Insider’s Guide: The Best of Cape Cod

18th June 2020

Cape Cod is a classic summer vacation spot that has been attracting families for generations — including my own. I started going here as a child, and now I take my own daughter. What I love is that not much has changed over the years.

There’s so much to see and do on Cape Cod, from visiting spectacular beaches and charming villages to putt-putt golfing to watching outdoor movies at one of the country’s last remaining drive-in movie theaters.

Here’s my insider’s guide to the best of Cape Cod.

Ocean Marshes at Sandwich, Cape Cod. Courtesy of Getty

Where to Go

A 70-mile-long peninsula that curls into the Atlantic Ocean, Cape Cod is home to some of the oldest villages in America. Near the entrance to Cape Cod is Sandwich, the most historic spot on the Cape. To the south is Falmouth, with a charming downtown and a windswept waterfront. Across a small spit is Woods Hole, a fishing village know for its famous oceanographic institute and a jumping-off spot for day trips to Martha’s Vineyard.

The biggest city on the Cape is that famous Kennedy enclave of Hyannis; it’s the place to catch the ferry to Nantucket. Dennis has plenty of family-friendly thrills (go-karts, squirt-gun boats, trampolines). The best-known town is Chatham, with its buzzing downtown, picturesque lighthouse and Friday night band concerts in summer.

The Lower Cape’s atmospheric villages include Brewster (nicknamed the Sea Captains’ Town), Harwichport (a former whaling center) and Orleans (the gateway to the national seashore).

After that, the peninsula gets narrower and the landscape wilder. Beachy Wellfleet is an enticing pit stop en route to Provincetown, also called P-town, an eclectic haven that attracts a mix of gay couples and families, artist and fishermen.

Courtesy of the Chatham Bars Inn/Facebook

Where to Stay

Nothing beats a stay at the historic Chatham Bars Inn, which was the first luxury hotel in Cape Cod, built by a wealthy Bostonian in 1914. Today, it’s a family-friendly getaway overlooking Chatham’s shifting Atlantic Ocean sandbars. Across town, the Wequasset is located on sailboat-filled Pleasant Bay and has a vintage ice-cream truck that passes out treats for kids; most of the guest rooms are in cottages scattered throughout acres of gardens.

Brewster’s Ocean Edge Resort & Club — set in an old mansion and villas on the waterfront — offers movies by moonlight and s’mores on the beach.

Another great place for families is the motel-style Crow’s Nest in Truro, which has full kitchens and opens right onto a pretty bayside beach.

The Cape is covered with old-fashioned bungalow hotels, and one of the most photographed is the Day’s Cottages in Truro. What it lacks for in luxury, it makes up for in charm.

Mac’s Shack in Wellfleet. Courtesy of Macs/Facebook

Where to Eat

No trip to the Cape is complete without a platter of fried clams. Mac’s operates a number of excellent seafood spots, from a shack on the dock in Wellfleet to a fish house in Provincetown. In Chatham, the Squire is a local institution, where crowds line up in the summer for live bands, a game room (which kids love) and simple eats.

Cap’t Cass Rock Harbor Seafood is a funky spot in Orleans with colorful buoys covering the exterior. An insider’s secret, Sesuit Harbor Café is hidden in a marina in Dennis. Arnold’s Lobster & Clam Bar in Eastham is known for its fresh seafood, mini golf and homemade ice cream. For amazing sunsets, head to Cataumet’s Chart Room Restaurant, a simple seafood haunt in a marina where crowds gather on the lawn to watch the spectacle. At Provincetown’s Red Inn in P-town, the view of the sun setting over the bay is so spectacular that you almost don’t even notice how good the food is.

The Beaches

If you’re a beach lover, you’re in luck. The Cape is lined with spectacular beaches. The protected Cape Cod National Seashore — with its wide, white-sand Atlantic beaches — stretches 40 miles, from Chatham to Provincetown. Don’t miss North Beach (reachable only by boat from Chatham), Nauset Beach or Provincetown’s Race Point, where you can spot whales offshore.

The other side of the Cape is lined with placid coves and appealing bay beaches. I love discovering hidden coves like Jackknife Beach in Chatham. One of my favorite places to visit is Lieutenant Island, which is only accessible at low tide. There’s a wild bayside beach here, hidden beyond the sand dunes.

Exploring with Arts Dunes Tours in Provincetown. Courtesy of Arts Dunes Tours


When you’re ready to peel the kids away from the beach, there’s plenty to keep the family entertained. The town of Dennis Port has plenty of family-friendly thrills (go-kart racing, squirt-gun boats, trampolines). With its flat terrain and paved bike trails, the Cape is perfect for cycling. Don’t miss the 26-mile Cape Cod Rail Trail, built on an old railway bed.

Another fun excursion is Chatham’s Beachcomber Boat Tours: Its bright-yellow vessels operate seal-watching tours and drop off passengers on secluded North Beach. The Cape Cod Museum of Natural History in Brewster has nature trails to explore, demonstrations by naturalists and even a resident beekeeper.

When we’re feeling adventurous we make our way to Provincetown, an artsy town at the tip of the Cape, where you can go on whale-watching tours with Dolphin Fleet Whale Watch. For kids, there’s nothing like seeing a humpback breaching on a whale-watching tour out of Provincetown. Kids also love exploring the dunes in four-wheel drives with Arts Dune Tours.

Strolling through Chatham, past the Candy Manor. Courtesy of Getty



While you don’t really come to the Cape to go shopping, there are several spots not to be missed. In Harwichport, Dr. Gravity’s Kite Shop in Harwich Port is a favorite stop for board games and beach toys. Chatham Candy Manor, in Chatham, is any kid’s dream: a classic sweets shop that sells fudge in every flavor: Marshmallow Fluff, Reese’s. The Brewster Store, an old-fashioned general store, sells just about everything you can imagine, from penny-candy to ice cream to puzzles.


Cape Cod isn’t exactly a cultural mecca, but there are some cultural highlights to keep the family entertained. One museum that is worth a visit is Yarmouth Port’s Edward Gorey House. The author, illustrator, puppeteer and playwright lived and worked here from 1986 until his death in 2000.

When I was a kid, I saw Jaws at the Wellfleet Drive-In, and now I enjoy taking my daughter. It’s one of the country’s last remaining drive-in movie theaters.

The Friday night concerts in the bandstand on the Chatham green are not to be missed; the whole town turns out.

Summer theater is big here. There are small-town play houses scattered throughout Cape Cod that put on theatrical productions. In Dennis, Cape Playhouse — one the country’s oldest professional summer theater — showcases performances for kids during the summer on Friday mornings. Cape Cod Theatre Company is home of the Harwich Jr. Theatre, which offers family programming with musicals like the Little Mermaid.

Getting Around

Depending on when you’re visiting Cape Cod, the traffic can be brutal. The main road that runs through the area is U.S. Route 6; for a more atmospheric drive, get off the highway and take Route 6A, which is also called “The Old King’s Highway” and winds through historic cottage-lined villages.

To the south is Route 28, which cuts through the southern Cape and is lined with all kinds of ticky-tacky summer activities that will make a child’s heart sing: putt-putt golf, petting zoos, bumper cart arcades and batting cages. There’s a public bus that roams the Cape, but a car is really the only way to get around.

By Laura Begley Bloom

For more on Massachusetts, see our Massachusetts Family Vacation Guide.

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