A friend told me that when someone tells him they love Cape Cod, he asks: which Cape Cod? There are so many different experiences to be had on the Cape that often what one person thinks of as Cape Cod can be entirely different from another. So in this post I am going to share my version of Cape Cod: summertime in and around Orleans. Here are my top things to do this summer if you vacation in Orleans, Massachusetts.

About Orleans

Orleans is a small town on Cape Cod located 35 miles east of the Sagamore and Bourne bridges. It’s known for being quieter and less crowded than many of its Upper and Mid Cape neighbors - e.g. Barnstable, Mashpee, Dennis, Yarmouth, Sandwich. It also has more downtown and year round businesses than Outer Cape towns such as Eastham, Wellfleet and Truro. It has beaches on both the Atlantic Ocean (“the backside”) and Cape Cod Bay (“the bay”), several freshwater ponds, and two major intracoastal bodies of water. The town has great restaurants, ice cream shops, art galleries, a farmer’s market, t-shirt shops, artist cottages, mini golf, hiking trails, kayaking, the Rail Trail, and so much more.

Let’s get started with our top things to do in and around Orleans:

#1: Go to the Beach

The main decision in choosing a beach is whether you want to be on the Atlantic Ocean or Cape Cod Bay. The Atlantic beaches have the best surf and offer some of the best vistas on the Cape, but they have one downside: sharks. Over the last decade the increasing seal population in the northeast has brought with them great white sharks. It is common now for sharks to prowl close to the beaches in search of their prey, with regular shark sightings occurring from the shore. If you choose to go to an Atlantic side beach, definitely follow shark safety guidelines. While there are many beaches to choose from, here are a few of my favorites:

Marconi Beach (Wellfleet, 11 miles) - This was our go-to beach on the seashore when our kids were younger. It has great surf, plenty of parking, and white sand beaches surrounded by stunning reddish clay bluffs. Nearby is a nice short walking path called the Atlantic White Cedar Swamp Trail, and a historic monument to the Marconi wireless station. The remains of the Whydah pirate ship was excavated decades ago off the shore just north of the main beach.
Nauset Beach (Orleans) - The iconic beach of Orleans is Nauset Beach, which is located along the eastern edge of the town facing the Atlantic. It has great views, good surf, lots of parking, restrooms and lifeguards. While the beach near the parking lot is less than a half mile long, it continues north and south to cover over seven miles of the coastline. The more remote sections of the beach are only accessible via long walks, driving oversand, or a boat.
Coast Guard Beach (Eastham, 6 miles) - This is the southernmost beach of the Cape Cod National Seashore, a 40 mile stretch of federally protected land that includes dunes, marshes, woodlands and ponds. This beach has one of the great Cape vistas, with the white painted Coast Guard Station at the top of a hill overlooking the green marshes of the Nauset Estuary. If you choose this beach, you might consider a nearby stop at the Salt Pond Visitor Center or drive up Ocean View Drive to see the Nauset Light lighthouse, which is featured on every bag of Cape Cod Potato Chips.

The Cape Cod Bay beaches vary by town but have less surf, warmer water, and often attract more families with younger kids. While lacking the stunning vistas of the seashore, they are also beautiful. While there is still the possibility of sharks, they are seen much less frequently along the shores of Cape Cod Bay. Here are a few of my favorites bay side beaches:

Linnell Landing Beach (Brewster, 5 miles) - The Brewster Flats are almost as iconic as the Cape Cod National Seashore. At high tide this area will look like any other beach, but at low tide the waterline pulls back over a mile to reveal vast stretches of sandy flats and tidal pools.
First Encounter Beach (Eastham, 6 miles) - This is my favorite of the several bay side beaches in Eastham. It is surrounded by green marshland and low sand dunes. It also has an interesting historical connection: it’s where the Pilgrims first encountered Native Americans on their short stay on Cape Cod before landing at Plymouth. There is also a short “lazy river” here which is fun to float down.
Skaket Beach (Orleans) - Located on Cape Cod Bay, it has limited parking but does have restrooms and lifeguards. Since it is on the flats, at low tide the waterline recedes far out, exposing tidal pools that are popular with kids. You will also see some giant boulders in the sand, remnants from the last ice age.
Rock Harbor Beach (Orleans) - Located on Cape Cod Bay next to a marina, it offers sandy stretches, tidal flats, a fishing pier, and a boat ramp. During low tide, you can walk out to the sandbars and explore the area. You can also see the famous “clam trees” in the channel, which make for some great photos. There is also another less used section of the beach on the other side of the channel with limited parking at the end of Dyer Prince Road.

#2: Go for a Bike Ride

The Cape Cod Rail Trail is one of the hidden gems of the Cape. It is a 25-mile paved trail that runs from Yarmouth all the way to Wellfleet. Built on the former location of a railroad line that went bankrupt in the 1970s, it is wide, flat and incredibly scenic. If you didn’t bring your bikes, you will find rental shops on Main Street in Orleans right next to the trail: Orleans Cycle and Idle Times Bike.

One of our favorite family trips is to head west on the Rail Trail from Orleans, get off near Route 137, and follow streets to The Brewster Store for a coffee break and some penny candy (about 12 miles roundtrip). Another favorite route is to head toward Eastham and Coast Guard Beach. You need to leave the main trail in Eastham to follow the signs to the beach, which will take you across Route 6, to the Salt Pond Visitor Center, and then back on a bike trail through the woods. It's a beautiful ride that will give you several great views of the estuary as you approach the Coast Guard Station. If you have energy left when you arrive at the beach, bike up Ocean View Drive until you reach the Nauset Light lighthouse. This is one of the most photographed lighthouses in the area.

#3: Kayak / Paddleboard

With the Atlantic Ocean, Cape Cod Bay, the Nauset Estuary, Pleasant Bay and 11 ponds, Orleans is not lacking for places to get on the water. If you own a kayak or paddleboard, there are several public landings and docks from which you can launch. You can also rent from Goose Hummock (Nauset Estuary), Pump House Surf & Paddle (near Nauset Estuary), SUPfari Adventures (Pleasant Bay), or Down Cape Charters & Boat Rentals (Pleasant Bay). Nauset Estuary and Pleasant Bay offer some of the best waterways to explore on Cape Cod. Depending on the time of year, you will likely see many different types of marine creatures, waterfowl and even seals. But what I enjoy most is the incredible scenery: from the green of the coastal marshes to the wildflower meadows of Fort Hill to the yellow-green of the Nauset Spit.

I highly recommend you plan your trip around winds and currents though. I personally only go out on days with little or no wind, and plan my return trip for a rising tide. I’ve watched many kayakers and paddle boarders struggle against an opposing current when returning from a trip due to poor planning (tip: if your trip seems delightfully easy at first because of the wind and current, it's likely your return trip won't be the same). One year my niece and her friends had to call home for a boat rescue from the Nauset Spit after tiring themselves out.

#4: Watch a Sunrise / Sunset

The sunrises and sunsets on the Cape are not to be missed. The best sunrises are on any Atlantic Ocean beach, and the best sunsets are seen from Cape Cod Bay. My go to places to watch the sunrise are Nauset Beach in Orleans and Fort Hill in Eastham. I like to bring beach chairs or a blanket with me to Nauset Beach, since sometimes the best color of a sunrise happens before the actual rise. Fort Hill offers a great view overlooking the green of the Nauset Estuary, and has a small parking lot at the top where you can watch the sunrise without leaving your car. For a sunset, Skaket and Rock Harbor Beaches offer great views, especially on evenings with a few scattered clouds. The Cape sunsets are so dramatic they can sometimes make an amateur photographer look like a professional.

#5: Powerboating

Powerboating is one of my favorite activities on Cape Cod. Your destination will likely vary based on what you want to do. The Atlantic Ocean is great for fishing, whale watching, seeing the National Seashore, and even day trips to Provincetown or Nantucket. Cape Cod Bay is great for fishing, traveling around Cape Cod, or just enjoying time on the water. Pleasant Bay and the Nauset Estuary make for fun places for a day at the beach, swimming, seal watching, exploring, and watersports (tubing, water skiing, wakeboarding).

There are no boat launches on the Atlantic side of the Cape, so if your plan is to go off the eastern shore, you must navigate your way through intracoastal waters to get to an inlet. The two inlets are: (1) the Nauset Inlet in the Nauset Estuary, or (2) the North Cut at the mouth of Pleasant Bay in Chatham (accessible from Little Pleasant Bay or Meeting House Pond in Orleans). Both inlets are considered challenging and not recommended for inexperienced captains. I regularly use the Nauset Inlet and even now will have an occasional white knuckle trip getting in or out. Access to Cape Cod Bay is much easier since you only need to find a nearby bay side launch to drop your boat in the water.

If you own a boat, you will find several launches in Orleans, Eastham, Brewster and Harwich. If you don’t own a boat, there are a few places you can rent one. If you are a member of Freedom Boat Club, you can book boats in several locations, including Chatham, Dennis and South Yarmouth. If you want to boat on the Nauset Estuary, you can rent an aluminum or pontoon boat at Goose Hummock.

#6: Cape Cod Baseball League

Eldridge Park, home of the Orleans Firebirds

The Cape Cod Baseball League (CCBL) is a summer league for top college athletes. Players are nominated by their coaches, drafted, and stay in the homes of local families where they live and work on the Cape. There are 10 teams from towns on and near Cape Cod, each with their own home field. Since it is one of the few wood bat leagues, it attracts a lot of scouts looking to see college players perform in conditions closer to the Major Leagues. Games are free to attend, and you will see people leaving blankets and chairs at the ballfields in the morning of a game to reserve their spot. The CCBL has seen many future Major League stars, such as Aaron Judge, Max Scherzer, Chris Sale and Jason Veritek. Orleans happens to have one of my favorite Cape League fields at Eldredge Park, which is home of the Orleans Firebirds. If you go with kids, at the end of a game the local players will stay around to meet fans and sign autographs. If you have a youth baseball player in the family, check out the clinics the players put on during the week.

#7: Sailing

I managed to sink the first sailboat I ever sailed as a young adult, so I really shouldn't be offering sailing advice. That said, both Pleasant Bay and the Nauset Estuary are great places for small sailboats, such as catboats and sunfish. Over the last few years I've also seen an increasing use of windsurfers and eFoils all the way out to the Nauset Spit. You can rent sailboats at Arey's Pond Boat Yard (Orleans), Down Cape Charters & Boat Rentals (Harwich, 4 miles), or Pleasant Bay Community Boating (Harwich, 3 miles).

#8: Walking / Hiking

If you like walking through nature, you will enjoy the walks of Cape Cod. These range from easy to moderate, taking you to widely varying landscapes - from the hills of Truro to the giant ocean-facing bluffs of the National Seashore to green estuaries of Wellfleet. During the Covid-19 lockdown, I obsessed over finding new places to walk, and explored much of the trails of the Lower and Outer Cape. My ultimate was a 28 mile “Thoreau Walk” along the Cape Cod National Seashore. Here are a few of my favorites, all within a reasonable distance from Orleans.

Great Island (Wellfleet, 18 miles) - Great Island is actually a peninsula in Wellfleet that juts out into the bay. With over 9 miles of trails and landscape that varies from estuary to pristine white beach to woodlands, it is one of my favorite places to visit. It is also a popular place with mushroom hunters. Pro tip: wear a swimsuit and pack a lunch to fully enjoy a private bayside beach.
Dune Shack Trail (Provincetown, 28 miles) - This is quite possibly one of the most dramatic trails of the Cape. It takes you up and down giant dunes, past cranberry bogs and scrub pines to a remote section of the Cape Cod National Seashore. You will also see the famous dune shacks of Provincetown along the way. Be warned though: this is all beach walking.
Pamet Area Trail (Truro, 20 miles) - The forested hills of the Pamet River Valley bordering the bluffs overlooking the Atlantic Ocean make for dramatic must-see vistas. If you do this trail, I recommend checking out the top of Bearberry Hill and going on the deer trail to the bluffs (watch out for poison ivy).
Fort Hill (Eastham, 5 miles) - What this trail lacks in length it more than makes up for in vistas. Park in one of the two lots, make your way to the top of the hill, and walk the trails that take you past a whaler captain’s home down to the estuary and through Red Maple Swamp.

If you would like to stay local, check out some of the many trails in Orleans, such as Kent’s Point, Nauset Marsh Trail, or Pochet Island.

#9: Fishing

A striper caught off the National Seashore

The Cape offers both saltwater and freshwater fishing. Your options will vary based on your access to a boat or willingness to pay for a charter. If you want to saltwater fish from the shore, there are plenty of great options. You can surfcast right from Nauset Beach, where you can catch big striped bass and bluefish. Some large stripers get pulled in on the Nauset Spit by night fishermen every season. The migrating stripers will also make their way into both Nauset Estuary and Pleasant Bay every season, allowing you to catch them right from the shore. The best time is usually right after high tide, as the flooding brings baitfish inshore to feed from the banks.

If you have access to a boat, you have outstanding fishing grounds within a reasonable distance, including Stellwagen Bank, Crab Ledge, Race Point, the Golf Ball, the Monomoy rips, and more. You can find almost any type of experience, from catching a trophy striper to a tuna. There are many charters available right in town too, including Dragonfly Sportfishing, Triton Unchained Fishing Charters and Uncle Charley’s Charters.

I always recommend a stop at Goose Hummock to talk to a fishing pro before making any trip. Their staff are always incredibly knowledgeable on all the local fishing spots.

#10: Swim at a Lake

Sometimes you may want a change of scenery, or maybe just to swim in a freshwater lake without a fear of sharks. With over 1,000 ponds on Cape Cod, there is no lack of places to go. Here are a few of my recommendations:

Great Pond (Eastham, 4 miles) - This is the largest pond in Eastham and one of the nicest. It has a great sandy beach.
Crystal Lake (Orleans) - You will see Crystal Lake on your left as you drive on Route 28 toward Harwich/Chatham. It is a big deep pond that is great for families. It unfortunately has limited parking, so plan accordingly.
Pilgrim Lake (Orleans) - Pilgrim Lake is in southern Orleans. It is a clear pond with space for parking about 20 cars.
Nickerson State Park (Brewster, 3 miles) - Cliff Pond offers great swimming in clear water and with a sandy bottom.

#11: Seal Watching

The seals start to make their way into the estuary in May, and by August you will find herds of them lounging on sandbars. The Cape has two types of seals: the smaller harbor seals, and the giant gray seals (500+ pounds). While they are surprisingly cute - sort of looking like puppies with their big eyes looking out from the water. But I’ve seen one too many YouTube videos of a 500 pound seal jumping in the back of a fishing boat to ever want to get too close. They are best seen from a boat, so if you don’t have one, you can either rent one or go on a tours (e.g. Nauset Boat Tours). But just kayaking or paddle boarding in the Nauset Estuary or Pleasant Bay will likely result in a few seal sightings.

I spend a lot of time passing seals in the Nauset Estuary. While the location of the herds will shift around throughout the season, I generally find them on my way to the Nauset Spit, near the fishing fleet, or sometimes on the sandbars at the entrance to the Nauset Inlet. Please make sure to view from a distance and stop or slow the use of your motor as you near them.

#12: Oversand

If you have a four wheel drive vehicle and are willing to pay for an oversand permit, you can go oversand in a few different areas of the Lower and Outer Cape. You will need all the requisite equipment - e.g. tire pumps, tow straps, shovel, tire gauge, wooden boards. The Town of Orleans offers two locations: Nauset Beach South and the Nauset Spit via Callanan’s Pass (which is closed due to storm damage as of this writing). Nauset Beach South will close for 7-8 weeks each summer due to nesting piping plovers, so check with Orleans Natural Resources before heading on the beach. I find the trails on Nauset Beach South to be much longer and more interesting, but the Nauset Spit is very popular with residents going to the beach for the day.

One of my favorite experiences is to pack a dinner and go to the Outer Beach with friends in the late afternoon (a.k.a. Nauset Beach South). We like to find a spot with a good view of both the ocean and Pleasant Bay, build a fire, and enjoy a nice glass of wine and dinner while watching the sun set over the bay. It is a quintessential Orleans experience.

The Cape Cod National Seashore also offers oversand permits in both Provincetown and Truro. The area around Race Point Beach is absolutely beautiful, with a trail going past the Long Point lighthouse. Unfortunately other sections of the seashore only open intermittently, so it’s important to check the updated map before going.

The typical Orleans oversand vehicle gets packed with food and drinks for the day, a firepit, beach chairs, volleyball nets, beach umbrellas, surfcasting rods, wind breaks, and more. My favorite time to go on Nauset Beach South is late May or late September when the crowds die down. If you go peak season, be prepared to see rows of RVs and camper vans lined up on the beach.

#13: Shellfishing

The Nauset Estuary and Pleasant Bay are filled with shellfish, including quahogs, steamers, razor clams, cherrystones, mussels, oysters, lobsters and more. I’ve been told there are places you can recreational dive for lobsters, but have never been able to pry this jealously guarded secret from the people who know it. But it is surprisingly easy to fill a bucket with fresh shellfish by just going a few feet into the water and digging.

The first step is to get a shellfishing permit. It is important to read the regulations before your first trip, which will include permitted locations and limits for keeping your shellfish. Unfortunately the Nauset Estuary and Pleasant Bay will periodically have a red tide bloom, so you will also need to pay attention to notifications on the town websites about shellfish closures.

Again Goose Hummock is a great place to go for both gear and recommendations. My favorite technique is to go swimming near the shore of the Nauset Estuary where you can feel the shellfish underneath your feet on the muddy bottom. All you need to do to collect your lunch is dive down and pull them up.

#14: Bird Watching

I’m not a birdwatcher so won’t be able to give a lot of detail here. That said, I know the Wellfleet Bay Wildlife Sanctuary in Eastham is one of the more popular locations on the Cape for birdwatchers. I have seen blue herons, egrets, hawks, cranes, bald eagles and more in the estuary. You might also want to check out the activities at the Massachusetts Audubon in Wellfleet, since they sometimes offer hikes and even birder boat trips. I wish I could tell you more, but unfortunately this one is just not my jam.

#15: Watersports

The two most popular locations for watersports in the area are Pleasant Bay and Nauset Estuary. Pleasant Bay offers a larger and more open area for boating, with fewer shallow sections to avoid. Nauset Estuary has Town Cove, a small and narrow section of the waterway that has the consistent depth you want for watersports. A prerequisite to watersports of course is that you have access to a boat, tube / skis / wakeboard, a spotter, and all the relevant safety equipment. If you are missing any equipment, stop by the Nauset Marine Store, where you will find everything you need.

#16: Go Out for Breakfast

When it comes to breakfast, I like to stay local and return over and over again to my favorite haunts. My go-to place is the Hole in One in Orleans on 6A, which has great options for breakfast and the best homemade donuts on Cape Cod. They also have indoor and outdoor seating. I do long for the day though that the Hole in One will return to its pre-Covid approach of having waitstaff - but admit the current order / sit / deliver approach only slightly diminishes from the great experience. The best breakfast sandwich on the Lower and Outer Cape can be found at Sunbird. This is also one of the better coffee shops in town. For the best experience, stop at Nauset Farms on your way to Nauset Beach for coffee and a breakfast sandwich. There is nothing like starting the morning watching the waves while eating breakfast and sipping a morning coffee from a beach chair. If you are looking for a morning bagel, you can’t do much better than JoMamma’s on 6A. And finally, if you are in the mood for a great breakfast burrito, stop by the Corner Store on Main Street.

#17: Antiquing & Vintage Shopping

Cape Cod is filled with antique and vintage shops for all types of shoppers. During the Covid lockdown, Kristin went to an antique shop in Dennis and while walking around overheard an early twenty something couple talking while they browsed. She was surprised by how enthusiastic the young man was about antiquing. When she went up to the cash register, the couple was already in line and she realized the young man was our nephew Alex. Unfortunately for her, antiquing must be a recessive gene in my family since I am mostly an unwilling participant on her trips. But here are her recommendations, all local to Orleans: Hidden Gems, Gallery at Post Office Square, Nauset Vintage, Garvey Rita Art & Antiques, and Yak Arts.

#18: Visit a Brewery

While there was a time not long ago when it was hard to find a brewery on Cape Cod, the micro brewery revolution of the last two decades has brought several good options to the Cape. The best local choice is Hog Island Beer Company (Orleans), which is a small brewery that offers food, drink and live entertainment on their lawn. While it’s a bit of a trek, Provincetown Brewing Company (Provincetown, 27 miles) is one of my favorite places for a good pint, with an eclectic atmosphere and surprisingly good food. For Mid Cape I like Devil’s Purse Brewing Company (Dennis, 13 miles), which has mostly been takeout since Covid-19 but previously had a small outdoor patio area. While there are many more breweries on the Cape - e.g. Tree House in Sandwich, Cape Cod Beer in Hyannis, Aquatic Brewing in Falmouth - I usually don’t venture much beyond Dennis once I am in Orleans, so will leave investigating those up to you. I will say though that Tree House has one of the best locations with a view (although all the actual brewing is done off-Cape).

#19: Mini Golf

There are few activities that feel more like summertime than mini golf. While there are several places to mini golf on Cape Cod, there are two in and near Orleans. Cape Escape (Orleans) is tucked back off a street behind the Route 6 rotary. It is Cape-themed, with boats, lighthouses, waterfalls and a koi pond. Arnold’s Adventure Mini Golf (Eastham, 7 miles) is on Route 6 and shares a parking lot with the attached restaurant. It is a pirate-theme with a ship and treasure chest.

#20: Visit a Bookstore

We are big readers and always enjoy a good bookstore. You will find great new and used book stores scattered throughout the Cape. Our favorite stores for new books include Sea Howl Bookstore (Orleans), Brewster Book Store (Brewster, 6 miles), and Yellow Umbrella Books (Chatham, 11 miles). For used books we like Herridge Books (Wellfleet, 14 miles) and Parnassus Book Services (Yarmouth Port, 20 miles). You might also want to stop at Snow Library in Orleans for their Saturday book sale.

It’s worth mentioning there are two must-read books that were written right in the local area (Orleans / Eastham). The first is The House on Nauset Marsh, by Wyman Richardson, which was written in the 1940s and captures the beauty of the Nauset Estuary in an era when it was much more rural and isolated. You will pass Richardson’s former house, which is still owned by his family, if you walk the Nauset Marsh Trail. The second book - and my favorite on Cape Cod - is Henry Beston’s The Outermost House, which chronicles a year the author spent living on the outer beach in Eastham in the 1920s. The beach shack Beston lived in was located not far from the northern side of the Nauset Spit. Unfortunately it was washed into the estuary during the great blizzard of 1978.

#21: Wine / Spirits Tasting

The Main Street Wine & Gourmet is one of our favorite local shops. They offer wine, beer, cheeses, and various other appetizers for entertaining. The owner is great, the staff very knowledgeable, and they regularly hold wine tasting events in the second floor back room. If your vacation doesn’t align with one of their events, you might consider stopping by the store on a weekend for their regular wine tastings (typically 3-6 PM on Saturday and Sunday). It’s a short experience, but always fun to try some wines and take home some appetizers for the evening.

While it's a bit of a drive, Truro Vineyards (Truro, 20 miles) is a beautiful venue for tasting their locally produced wines and spirits (gin, whiskey, rum). Advanced reservations are almost always required, and you can try out different flights of their products.

#22: Learn Some History

If you are a history geek like me, there is a lot of interesting history to learn on Cape Cod. The area was inhabited for thousands of years by the Nausets, a Native American tribe that farmed and fished these lands. The Pilgrims made their first landing in North America right here on the Cape before heading off to found the village of Plymouth. The Cape also has connections to key historical events - e.g. the first wireless telegraph, a minor battle at Rock Harbor during the war of 1812, an attack on Nauset Beach by a German submarine in World War I, and so much more. So if history is your thing, here are a few suggestions:

Atwood Museum (Chatham, 11 miles) - This is quite likely the best history museum on Cape Cod. The main museum includes a 1752 sea captain house that transports you back to a long lost way of life in Chatham. Built on to this house is the main museum, which includes a diverse collection of paintings and artifacts from many different eras. The highlight for me was the real North Beach dune shack (a.k.a. camp) they have on the grounds.
Whydah Pirate Museum (West Yarmouth, 21 miles) - Black Sam Bellamy was one of the most prolific pirates on the seas before he wrecked his ship in a storm off Marconi Beach in Wellfleet. This museum is dedicated to telling the story of pirates on Cape Cod, and showcases many of the artifacts from the salvage of the Whydah wreck. I know it sounds cheesy, but I really like this museum. Interesting fact: John Kennedy Jr. worked on the salvage of the Whydah in the 1990s.
Cape Cod Museum of Natural History (Brewster, 12 miles) - This museum has exhibits for local wildlife, marine life, geology, and Native Americans. It also includes a great trail that takes you on to the Brewster Flats. Check out their guided walks.
Eastham Historical Society (Eastham, 6 miles) - There are actually two locations for the Eastham Historical Society and I would highly recommend you visit both. The first is right on Route 6 near the Superette and includes a 1741 farmhouse, a beach camp from the Outer Beach, and a toolshed. The second location is located on School House Road across from the Salt Pond Visitor Center, and includes an 1869 schoolhouse and a main museum with an assortment of artifacts. The volunteers who staff these two locations are what make this such a great experience. We actually got a tour from the granddaughter of one of the previous owners of the farmhouse.
Pilgrim Monument & Provincetown Museum (Provincetown, 30 miles) - The Pilgrim Monument rises from the landscape at the tip of the Cape. It commemorates the hot minute the Pilgrims spent on Cape Cod. You can visit the museum and climb to the top of the monument for a great view of the local area.

#23: Cocktails With Atmosphere

We enjoy an occasional cocktail out on the Cape and have a few go-to places. Our favorite for happy hour (3:30-5:00) is Caroline’s Cape Cod Bar & Grill (Eastham, 5 miles), which opened in 2021 and has been bringing in the crowds. They have live entertainment and $1 oysters during happy hour. We also enjoy the Wequassett Resort & Golf Club (Harwich, 5 miles), which has multiple great venues for having a drink. We particularly like the outdoor bar (LiBAYtion) and patio (The Verandahs) - but Thoreaus is also a good choice if you want an indoor venue. A last recommendation is Ocean’s Edge Resort & Golf Club (Brewster, 6 miles), which also offers multiple options. The Ocean Terrace, Front Lawn and Shark Bah are all great venues for drinks.

#24: Plan a Lobster Night

One of our extended family traditions is Lobster Night (a.k.a. Lobstah Night). We usually designate a night toward the middle of vacation when the refrigerators are packed with leftover sides from our previous dinners. We start the day by finding who in the family wants lobsters and/or steamers. We place the order with a local market early, ask them to steam everything for us, and then at dinner time lay out all the sides before picking up the order. We usually go with a 1 ½ pound lobster and ½ pound of steamers per person - although this is an annual debate between my sister and I (I still think 1 pound of steams per person is better). While there are many reputable markets in the area to choose from, my go-to is the Nauset Fish Market and Lobster Pool on 6A.

In a family of six kids, six spouses and 16 grandkids, there are a few poor misguided souls who don’t like lobster. My brother Steve for example has very specific rules around what he will eat, and his rule #2 says: “Don’t eat something that looks like it did when it was alive.” Yeah, lobsters are a strong fail on this rule. My nephew Dan is also not a big seafood fan, claiming that eating shellfish is like “dragging my open mouth along the bottom of the ocean.” But for the rest of us, it is our favorite dinner of the week.

#25: Trip to Provincetown

Race Point Light from the oversand trail

A trip to Cape Cod is incomplete without a visit to Provincetown. In addition to its picturesque beaches, charming downtown, great restaurants, art galleries, and a vibrant nightlife, it is also an LGBTQ+ friendly town known for its inclusiveness. No two Provincetown visits are the same. Once we brought a friend of Kristin’s who had never been to Provincetown. After a walk around town, we stopped for lunch at the Nor’ East Beer Garden. When Kristin and her friend started talking about their favorite TV show (Real Housewives), two men at the bar turned around to join in on the discussion, with one being a well known Real Housewives TikTok influencer. The entire conversation bordered on a comedy skit, as the four of them talked about different reality characters as though they were close personal friends.

Since there are too many places to see and visit for me to give you a complete list of to-dos in Provincetown, here are a few of my favorite places:

Race Point Beach - This is one of the ironic beaches of the Cape Cod National Seashore, and a great place to spend the afternoon at the beach.
Province Lands Visitor Center - This is one of the two visitor centers of the National Seashore. I particularly like this once for the view of the Province Lands from the upper deck.
Penny candy, fudge & ice cream - When our boys were younger, one of their favorite activities was to walk down Commercial Street and stop at penny candy stores.
Dune Shack Trail - We discussed this walk in a previous section but it is worth repeating here. It is one of the best hikes on Cape Cod.
The Red Inn - There are so many great places to go for food and drink in Provincetown that I feel bad to single one out. But The Red Inn has a great back porch that steps down onto a white sand beach along the harbor. It also has Adirondack chairs you can sit in while sipping a cocktail and enjoying the views.
Province Lands Bike Trail - There is a great bike trail that goes through the Province Lands, with beautiful vistas of dunes and water.
Wood End hike - Cape Cod is shaped like an outstretched curled arm, with the fingers of this arm being a remote area known as Wood End. This area includes two lighthouses, Long Point Beach and lots of sand and dunes. You can get to Wood End by walking across a mile long rock jetty known as the Provincetown Causeway. Plan this walk around the tides, since some high tides will wash over the causeway.
Pilgrim Monument & Provincetown Museum - We covered this already under history but is worth mentioning again here.
Drive oversand - Near Race Point Beach are two entrances to the oversand trails. You will need to have a permit and the required equipment to enter the trails. These are usually open year round.

I could go on here but you get the idea. I recommend you check out a few travel guides before making this trip to maximize your visit.

#26: Go Crabbing

Years ago while getting my hair cut in Eastham, I asked a barber if he had any recommendations on things to do with young kids on Cape Cod. He suggested we go crabbing at Meetinghouse Pond in Orleans. My boys were nine or ten at the time, and talked all day about our plan to go crabbing that night with their cousins. There was so much excitement that I began to worry the event might be a bust. But as dusk was falling, my brother and I drove to the pond with a van filled with boys. We walked out on the dock and cut lengths of twine to which we attached raw chicken wings (don’t forget the hand sanitizer!). Within seconds of lowering the wings to the bottom of the pond, my boys were pulling up blue crabs. They learned quickly that the crabs would let go once they saw the surface approaching, and adapted to having a second person gently put a net underneath the crabs before they let go.

Over the next couple hours we had a great time catching and releasing our crabs. We probably caught 40 or more crabs (or maybe we caught one crab 40 times). The cousins competed to catch the biggest crab, and everyone busied themselves to support anyone who shouted: “I got one!”. As the evening wore on, the boys’ older cousin pulled up what has forever been known as Crabzilla. It was a giant spider crab that was so large he couldn’t fit in our net. He stared at us menacingly as he neared the surface before letting go, never to be seen again. In the years since, the size of Crabzilla has increased with each retelling of the story.

#27: Visit a Farmers Market

I’m always a little skeptical of farmer’s markets and stands on Cape Cod, since many of them just import their produce from off Cape. In many cases, you are better off going to your local grocery store than a nearby farm stand. But I do like the Orleans Farmers’ Market on Colony Way, which brings together a collection of local vendors that sell everything from produce to meats to honey. Another great choice is the Chatham Bars Inn Farm (Brewster, 3 miles), which has a farm stand and a working farm that provides the produce for the luxury resort of the same name.

#28: Go Out to Dinner

The food of Cape Cod is so varied that it’s hard to give a list of restaurant recommendations without first telling you my biases. So here they are: (1) I like casual restaurants that I don’t feel out of place wearing shorts, (2) while I may occasionally eat at a fried seafood restaurant on the Cape, I rarely find one I recommend, (3) the price of dinner should be aligned with its quality or I usually don’t return, and (4) I am all about great service and experience. So with that said, here is my favorite restaurant per town in or near Orleans:

The Pheasant (Dennis, 17 miles) - I’m going to make the bold claim that this is the best restaurant on Cape Cod. This former classic Cape Cod seafood restaurant was taken over a few years ago by a couple from Brooklyn who renovated the restaurant and menu. The menu makes heavy use of local ingredients and sustainable wines, and includes a variety of shared plates that can be ordered like tapas. We love to sit at the bar and have one of their custom cocktails with our dinner.
3 Monkeys (Harwich, 11 miles) - Three Monkeys has an Asian-influenced menu that includes sushi, ramen and bahn mi sandwiches. Its location along the main street in Harwich is ideal, with outdoor seating that puts you right in the middle of the action. You might want to add some pre-dinner shopping or a visit to The Nines Gallery while you are here.
Bluefins Sushi & Sake Bar (Chatham, 10 miles) - This American-influenced Japanese restaurant is located right on Main Street in Chatham. They are always busy and consistently serve good food. My nephew told me after coming here for the first time that this was the best dinner he had on the Cape.
The Brewster Fish House (Brewster, 5 miles) - With a contemporary bistro-style menu and a nice bar, the Brewster Fish House delivers consistently good food and service. This is a go-to place for us in the off season.
La Bella Vita Kitchen and Bar (Orleans) - This is our favorite local place for a good dinner. It is an Italian restaurant with indoor and outdoor seating. It's also a nice place to have a drink outside by the firepits.
Mac’s Shack Wellfleet (Wellfleet, 13 miles) - Located on an estuary, this restaurant has both indoor and outdoor seating. The outdoor seating includes a long open bar that is my preferred place to sit. The food and service is consistently solid. You can make a quick after dinner stop at Uncle Tim’s Bridge while you are here.

#29: Visit an Art Gallery

There are lots of great art galleries on Cape Cod for anyone interested in art at any budget, and I won’t pretend to give you a definitive list. But here are three of our favorite stops:

The Nines (Harwich Port, 11 miles) - This is our favorite artist-owned gallery on the Cape. The oil paintings and photographs are high quality and incredibly unique, the owners are really friendly, and the gallery is super classy.
The Frying Pan Gallery (Wellfleet, 13 miles) - There is a lot of unique art in this gallery, with my favorite being the steel marine sculptures. It’s located right on Wellfleet Harbor, with a second location in Orleans on 6A (which I have not yet visited).
Artist Cottages at Orleans Market Square - Several of the towns of Cape Cod have their equivalent of the artist cottages in Orleans. These bring together a collection of local artists in one locale where you can shop for a variety of art, jewelry and clothing.
Eastham Painters Guild (Eastham, 4 miles) - You will find this outdoor art market across from the Salt Pond Visitor Center on scheduled days. It is one of the better places to see paintings from various artists in one place - many at affordable prices.

#30: Visit a Lighthouse

There is something about a lighthouse that fascinates many of us. Maybe it is the scenic views, the rhythmic sound of crashing waves, their symbolism of hope, or the romanticism of another age. Whatever it is, visiting a lighthouse is a fun activity for all ages. There are 14 lighthouses on Cape Cod, with three on the Lower Cape and six on the Outer Cape. Here are five within a reasonable distance of Orleans:

Nauset Lighthouse (Eastham, 6 miles) - This lighthouse was built in 1877 in Chatham and moved in 1923 to Eastham to replace one of the Three Sisters lighthouses. Located on Nauset Light Beach, this lighthouse is operated by a non-profit and is open in-season for visits on Wednesdays and Sundays. This is considered by many to be the most beautiful lighthouse on Cape Cod.
Three Sisters Lighthouses (Eastham, 6 miles) - The Atlantic coast of Cape was one of the most dangerous areas to shipping through the 19th century. It was known as the “Graveyard of the Atlantic”, where thousands of ships would see their demise. The Three Sisters were originally built as masonry towers in 1836 before being replaced by wooden ones. While they are no longer active, they can be visited at their current location on Cable Road.
Highland Lighthouse (Truro, 20 miles) - The original lighthouse here was commissioned by George Washington in 1779 and became the 20th lighthouse in the United States. Its replacement you see today was built in 1831 and is located today next to a golf course. You can view the tower and the Highland House Museum in the same visit.
Chatham Lighthouse (Chatham, 12 miles) - Located on a site managed by the US Coast Guard and across from Chatham Light Beach, the original tower was a twin built in 1808 and replaced in 1841. The twin now resides in Eastham as Nauset Light. Unfortunately this lighthouse is not open for visits.
Stage Harbor Light (Chatham, 11 miles) - Built in 1880, this lighthouse is located at the mouth of the iconic Stage Harbor. You can see it with a short walk from Hardings Beach, or you can view it from the other side of the inlet from the Morris Island Trail, which is one of my favorite Chatham walks.

If you are serious about seeing as many lighthouses as possible and willing to hike, there are three more lighthouses to be seen in Provincetown: Race Point (best seen with an oversand drive or walk on Hatch Harbor Trail), and Long Point / Wood End (best seen with a walk across the Provincetown Causeway).

#31: Go Out to Lunch

I usually like to stay relatively local for lunch. Here are a few of my favorites:

Mac’s Market & Kitchen (Eastham, 9 miles) - Mac’s offers great sandwiches and outdoor picnic tables for seating.
Hole in One (Orleans) - The Hole in One has indoor and outdoor seating and a wide range of menu items. I particularly like their homemade potato chips.
Cibo Italian Kitchen & Market (Orleans) - This has been a relatively new addition to the town. Cibo’s has great food, great service, and you can eat inside or out.
Mac’s Shack Wellfleet (Wellfleet, 13 miles) - Yes there is a second Mac’s on this list. If you are in Wellfleet, this is always a great place to stop for lunch.
Bookstore & Restaurant (Wellfleet, 13 miles) - I’ll add one more go-to Wellfleet lunch spot: the Bookstore & Restaurant. It’s right on the pier so you can walk across the parking lot for great water views. One of my favorite hikes, Great Island, is just down the road.

#32: Listen to Live Music

Orleans has live music in several locations. The Nauset Beach Summer Concert Series is a great way to enjoy music with a view. There is also regularly live music at the Artist Cottages at Orleans Market Square, and downtown at the Orleans Community Center or in front of the Trove Gallery. The Wequassett Resort and Golf Club also has an annual jazz festival that is worth checking out.

Many of the nearby towns offer similar opportunities for live music that you will find in Orleans, so definitely check out town websites and event calendars.

#33: Go to a Drive-In Movie

Even if you were born long after the era of the drive-in theater, there is still something nostalgic about watching a movie on a giant outdoor screen from the comfort of your car. With drive-ins increasingly becoming an endangered species across the country, we have the luxury of having one right in our backyard. The Wellfleet Drive-In Theatre (Wellfleet, 8 miles) is a great place to go with the whole family to watch a movie on a warm Cape Cod summer evening. Plan to arrive early since the best viewing locations get filled quickly.

#34: Go Out for Ice Cream

Growing up with a dad who loved ice cream, a trip to the local shop was a childhood ritual. I still remember my dad coming outside at dusk with us kids playing in the yard and saying: “Anyone want ice cream?” Everyone would shout “Yes!” and scramble into the back of his giant red station wagon. I’m pretty sure he didn't know which neighborhood kids were in the car with us as he drove away.

After we grew up and started our own families, my dad continued the tradition with his grandkids on Cape Cod. At least a couple times during our extended family vacation he would ask: “Anyone want ice cream?” Within minutes he would be surrounded by a gaggle of grandkids who would walk with him to the nearest ice cream shop. I always thought it odd that he never changed his order: maple walnut. I learned recently that when he was a child there were only three types of ice cream, and maple walnut was one of them.

My go-to is the Ice Cream Cafe right near the Orleans rotary. But Smitty’s Homemade Ice Cream on Beach Road or Emack & Bolio’s Ice Cream on 6A are also great choices. You can’t go wrong when it comes to ice cream.

#35: Dinner at the Beach

We have a tradition when we gather with my extended family for a Cape Cod vacation that each of the six siblings take turns making dinner one evening. This simplifies the coordination around dinner, which is especially complex in a large family. But there was always one night that no one covered. One year we decided to fill this slot by ordering pizzas and bringing them to the beach. Since beaches stop charging for parking in the evening, it provided the least expensive waterfront dining on the Cape. It was such a success that we have repeated this many times over the years.

This last year my sister decided to incorporate a beach dinner into her cooking night. We helped her bring everything she needed to First Encounter Beach - e.g. beach chairs, a serving table, hot food in covered trays, plates, silverware, drinks, wind breaks, garbage bags, towels, beach toys. We set up our chairs in a giant circle and ate while watching the sun setting over Cape Cod Bay. It was… perfection.

#36: Find the Perfect Lobster Roll

I don’t remember where or when I had my first lobster roll, but that moment was clearly the beginning of a lifelong love affair. Having grown up far from lobster country, I was not aware of the great New England debate regarding the Maine versus Connecticut question. For those of you not already briefed, here is the TLDR. Maine lobster rolls are served cold, with the lobster meat tossed lightly in mayonnaise and heaped on a toasted Frankfurter roll. Connecticut lobster rolls are served warm and doused in melted butter. While there are many minor variations of these themes, all lobster rolls will fall in one of these two categories.

While I am an omnivorous lobster roll eater, as a resident of Massachusetts, I know which side my lobster roll is buttered on (Maine of course). That said, every year on the Cape I continue my lifelong quest to find the perfect lobster roll. Some people say it can be found at the Sesuit Harbor Cafe (Dennis, 11 miles), the Friendly Fisherman (Eastham, 6 miles), Chatham Pier Fish Market (Chatham, 11 miles), or Mac’s Shack (Wellfleet, 13 miles). I have tried them all and will admit they are excellent. But to date, the best lobster roll I have had on Cape Cod is found only in one place: in my kitchen in Orleans. But since it is not yet perfect, the quest continues.

#37: Watch a Movie

Since much of the enjoyment of the Cape happens outdoors, rain can definitely put a damper on a vacation. Our go-to option for a rainy day is to watch a movie at home. While our choices usually range from Top Gun to the most recent Marvel Comic release, there are a few Cape-themed movies worthy of consideration:

The Finest Hours (2016) - This is based on the true story of a 1952 Coast Guard rescue after the sinking of the SS Pendleton during a severe winter storm. The events take place in and near Chatham, and this is considered the greatest small boat rescue in marine history. After watching the movie you can visit the Coast Guard boat used in the rescue at Rock Harbor in Orleans.
Jaws (1975) - While the fictional Amity Island was off Long Island, much of the filming took place on the Cape and the Islands, with Martha’s Vineyard and Provincetown being two key locations. This is a classic that never gets old.
Give or Take (2020) - This is a story about a man who returns to his childhood home to get it ready for sale after the death of his father. It was filmed in multiple locations across the Cape, but highlights several in Orleans, including the restaurant Land Ho.
Starboard Light (2015) - This is a documentary of five generations of a family and their vacation home in Chatham.

#38: Take a Plane Ride

A friend made me an offer I could not refuse this summer: to take the third seat on his plane tour of Cape Cod. We met at Chatham Airport, where our pilot Jimmy from Stick’N Rudder Aero Tours was waiting for us. We piled into a small four seat Cessna for an hour long ride that brought us up the Outer Cape on the bay side, then down the Atlantic side. We passed over Chatham, Harwich, Brewster, Orleans, Eastham, Wellfleet, Truro and Provincetown. The highlight for me was flying around Monomoy National Wildlife Refuge. The pilot even took the time to fly over my house. I realize this is likely the most expensive recommendation on my list, but I honestly think the experience justifies the cost. If you haven't taken a plane tour of Cape Cod yet, I would highly recommend it.

#39: Visit the Paranormal

Have you heard the story of Goody Hallett, the lover of the infamous pirate “Black” Sam Bellamy, whose ghost haunts the dunes above Marconi Beach? Or the first documented case of UFO abduction which happened at Salty Market in Truro? What about the ghosts that haunt the Orleans Waterfront Inn, which were documented in an episode of the SYFY channel series Ghost Hunters? These are just a few of the many great paranormal tales of Cape Cod.

Some of the best tours are the ones you create with your own internet sleuthing. On a recent family vacation, we visited three spots in Truro: the haunted Highland House, the site of a 1966 alien abduction, and a visit to the always spooky abandoned Air Force Base. But if you would prefer to have a guided journey into the paranormal, consider going on the Cape Cod Haunted & History Tour (Barnstable, 23 miles), or the Provincetown Ghost Tours (Provincetown, 29 miles).

#40: Float Down a Lazy River

Floating down a lazy river on an inflatable is a unique Cape Cod experience. It is also an activity that takes a little planning to be safe and enjoyable. The “lazy rivers” on Cape Cod are really tidal creeks in estuaries whose currents change with the incoming and outgoing tides. The nearest one to Orleans is Bee’s River, which runs through the marsh behind First Encounter Beach in Eastham. While you will see riders on it during an outgoing and incoming tide, some people say it’s safest to ride up the river with younger kids (i.e. incoming tide) - but to be careful to get off before you get pushed too far back in the marsh. Others however say the best ride is going down the river (i.e. outgoing tide), but to be aware there is a strong current and a dropoff as the river enters the bay. I’ll let you figure out what is right for you, but will pass on a few tips: 1) time your ride for the tide change but be aware the river current usually lags behind the tide tables, 2) don’t let the slow current at the start deceive you since it will pick up speed over time, and 3) make sure to supervise younger kids to ensure they ride safely.

We recently did a great lazy river ride in Sandwich down Scorton Creek that dropped us at Craven’s Landing by Scorton Harbor. We had 20 floats lashed together with carabiners, brought music with us, and had a great day on the water.

#41: Golf

What stands between me becoming an average golfer is about 10K hours of practice. My life hack for all that frustration and hard work is simple: I don’t golf. But since I know some of you are golfers, I will list this as one of the activities to do in and around Orleans. Here are some of the popular courses in our area:

The Captain’s Golf Course (Brewster, 6 miles) - This course has two championship courses for a par-72.
Highland Links (Truro, 22 miles) - This course is located on the bluffs overlooking the National Seashore, making it one of the most beautiful on the Cape. You can visit Highland Light and Highland House while you are here.
Cranberry Valley Golf Course (Harwich, 13 miles) - Includes a driving range and short game practice area that is touted as one of the best on the Cape.
Chatham Seaside Links (Chatham, 12 miles) - Located right next to the beautiful Chatham Bars Inn, this makes for a beautiful course located near downtown, a beach and a fishing pier.
Ocean’s Edge Golf Course (Brewster, 6 miles) - This is a private course only available to resort guests, but is one of the most beautiful on the Cape.

#42: Trip to the Islands

One of the most popular activities we with my extended family is to make a day trip to the islands, where we visit beaches, shop, dine, and enjoy the beautiful vistas. We usually prefer Martha’s Vineyard for a day trip, but Nantucket is also a great fun. Some years we brought our car over, other times we carried bikes, and a few times we rented mopeds or Jeeps. While you can visit Nantucket on foot, Martha's Vineyard does really require some form of locomotion.

The ferries have been booking up quickly over the last few years, so this activity does require a little advanced planning. If you are going to Nantucket, you can leave from Harwich on Freedom Cruise Line (80 minutes), or from Hyannis on Hy-Line Cruises or the Steamship Authority (60 minutes). For Martha’s Vineyard, you will need to leave from Hyannis on Hy-Line Cruises (80 minutes), or make the long trek to Falmouth for some additional ferry options.

For Martha's Vineyard, we always enjoy a trip to the Aquinnah Cliffs, a walk through the Oak Bluffs Campground, a visit to Chappaquiddick, a stop at the Edgartown Lighthouse, and of course a visit to the "Jaws bridge."

#43: Plan a Game Day

World Corn Hole Classic Championship Trophy

If the Kennedy’s were famous for their touch football on the lawn of the Kennedy Compound, the Kinsellas are a lot less famous for our volleyball. We started this tradition when our children were small, and unfortunately our kids’ skill level has increased far beyond our ability to compete. So more recently we have added cornhole into the mix, with our self-created World Cornhole Classic. One of my nephews organizes the teams and brackets, another films the event and produces a humorous video, and everyone competes to win the championship trophy: a 3D printed trophy of a figure throwing a bean bag (spray painted gold to look valuable of course).

Whatever your games of choice are, there is almost always time and a place for organizing a game day. It’s inexpensive, fun, and a great way to spend the day with family on Cape Cod.