Everything You Need To Know Before Your First Trip To Cape Cod

Stretching out like an arm from the rest of Massachusetts, Cape Cod beckons visitors to play in the sand, eat plenty of “lobstah” rolls, and watch the sun shimmer over the water as it sets. With delicious, local food, abundant opportunities for both outdoor excursions and lazy beach days, a thriving arts scene, and lots and lots of ice cream possibilities, the hardest part of visiting the Cape is deciding how to make time for everything. Spoiler: There’s too much to cover in one week, so you’ll just have to make your Cape Cod vacation a yearly tradition.

Find your favorite beach.

A trip to the Cape isn’t complete without plenty of time in the sand, and both quiet and lively beaches line the shore and the bays. Check out Nauset Light Beach, a popular mile-long sandy stretch in Eastham that’s part of the National Seashore. Those who get antsy in the sun can go surfing or swimming or walk over to get your lighthouse fix at the Nauset Light or the Three Sisters lighthouses. For a family-friendly beach atmosphere on the Mid Cape, consider heading over to busy Craigville Beach. When it’s time for lunch, just pop across the road to The Barnacle for fuss-free seafood options including lobster rolls and shrimp tacos, as well as homemade potato chips. Sister shop The Barnacle Too has pizzas and subs. Pro tip: Make friends with locals wherever you are staying, and ask for their favorite spot.

Create your own ice cream tour.

Although most serial summer visitors have their favorite ice cream spot, sampling the plentiful options on the Cape is a large part of the fun. Four Seas in Centerville has been around since 1934; the ultra rich and creamy ice cream was beloved by generations of Kennedys. Sundae School has several locations including their main one in a charming renovated barn in Dennisport. Other favorites include Katie’s on Main Street in Hyannis and Cape Cod Creamery. Also irresistible: the coffee-flavored soft serve topped with sprinkles or dip at Steve and Sue’s Par-Tee Freeze.

Pick a seaside town to explore.

Driving onto the Cape on a summer Saturday is enough to make you want to find a place in the sand and park it for a few days, but don’t miss out on mini road trips to the numerous charming towns. Chatham, located on the southeastern tip of the Cape, has a Main Street with unique jewelry, clothing, and gift stores that are perfect for stocking up on souvenirs. And there’s the must-visit Chatham Candy Manor to satisfy your sweet tooth. Pick up some beach reading material at Where the Sidewalk Ends, and stop at The Impudent Oyster, just off the main drag, for a drink or delicious upscale bar fare with a focus on seafood. For a splurge, grab a meal at the gorgeous Chatham Bars Inn (we like The Beach House for its unparalleled views) or book a treatment at their luxurious day spa. You can even stroll down to watch the day’s catch come in at the Chatham Fish Pier.

Bike your way through the landscape.

Biking is a great way to experience some classic Cape scenery. The Old Rail Trail passes through towns including Dennis, Harwich, Brewster, Orleans, Eastham, and Wellfleet. Along the way, cyclists will see the terrain change from cranberry bogs and marshlands to forested areas. Avoid saddle fatigue by packing a picnic or riding into one of the towns. Bike rental outfitters dot the path if you didn’t bring wheels of your own. Runners and walkers are also welcome!

Indulge your inner artist.

Provincetown’s history as a haven for artists dates back to the 1800’s. The picturesque scenery and once-affordable housing offered creatives an escape from bustling New York or Boston, and gave them the opportunity to become inspired and refreshed on the Cape’s northern tip. With dozens of galleries representing artists in every medium, you could spend all your days strolling and admiring their work…or brush up on your own skills with a class at the Provincetown Art Association and Museum. Provincetown’s nightlife scene is just as colorful as the artwork with drag shows, live music, and a Friday Night Gallery Stroll.

Go whale watching.

Although Cape Cod and its surroundings have a reputation for attracting more than their fair share of great white sharks (Jaws was filmed on nearby Martha’s Vineyard), a more gentle and gigantic mammal is the focus of most tourist boating ventures: the whale. Day trips with The Dolphin Fleet of Provincetown or Hyannis Whale Watcher cruises explore Cape Cod Bay and the Stellwagen Bank National Marine Sanctuary to the north. Each cruise has a naturalist on board to help curious passengers identify whales, dolphins, and, yes, even the occasional shark.

Settle in for a movie, snacks, and some nostalgia at the Wellfleet Drive-In.

Watch new movies in an old-fashioned setting at the Wellfleet Drive-In, the Cape’s only drive-in movie theatre. Stop in early for a round of mini-golf (another beloved Cape activity), and then grab some popcorn or candy before settling back in your car. The nightly double feature isn’t the only reason to visit this fun entertainment throwback spot. The grounds become a flea market with up to 200 vendors multiple days each week, and there’s also a Beer and Wine Garden and a playground.

Make time for museums.

For days when the rain won’t stop (or sunburned skin needs a little R&R), visit one of the quirky or educational museums that crisscross the Cape. The Sandwich Glass Museum includes a daily glass blowing demonstration as well as exhibits featuring the works of contemporary and historic glass artists. The Edward Gorey House celebrates the art and life of the cult favorite author, illustrator, playwright, and costume and set designer. Cape Cod Museum of Art in Dennis highlights the works of artists with a link to the region. And there’s also the JFK Hyannis Museum for history buffs.

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