The Insider’s Guide to Cape Cod

You probably know Cape Cod as a beloved summer destination, but this arm-shaped peninsula on the coast of Massachusetts definitely has year-round appeal. While tourist season is in full swing from Memorial Day to Labor Day, insiders soak up the Cape’s natural beauty, cultural activities and crazy-fresh seafood in all months—there has to be a good reason to brave those harsh New England winters, right? Live like a local and enjoy some of these hidden and not-so-hidden attractions that draw visitors, “washashores” (that’s Cape-speak for transplants who never left) and natives alike.

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Smith Family Popcorn

Smith Family Popcorn, Hyannis

Located on historic Main Street in downtown Hyannis, this shop upgrades the humble kernel to delicious heights in flavors like sea salt caramel and cinnamon toast, all made with top-quality ingredients right on the premises. If savory is more your style, try the Tuscan Joy (a blend of olive oil, basil, garlic and sea salt that pairs perfectly with a glass of wine). Best of all, this family-run favorite ships worldwide and donates at least 5 percent of each sale to a local charity of your choosing.

545 Main St., Hyannis;

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The Red Inn/Facebook

The Red Inn, Provincetown

With sweeping views of Cape Cod Bay, a raw-bar happy hour and Sunday jazz brunch, this P-town favorite has welcomed weary travelers for more than a hundred years. Lunch and dinner reservations are recommended, but if you’re on a last-minute excursion to the Cape’s outermost town, drop in for sunset cocktails on one of the lawn’s harbor-facing Adirondack chairs, where you’ll be sure to fall in love with Old Cape Cod. 

15 Commercial St., Provincetown;

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Sunbird Cape Cod/Facebook

Sunbird Kitchen, Orleans

This casual Lower Cape café outpost boasts the area’s best coffee (of particular importance for discerning New Yorkers) and an inventive and ever-changing menu that includes options ranging from the healthy (quinoa porridge with coconut milk and lavender honey) to the indulgent (Mexican chocolate doughnuts). The shop’s retro-chic interior wouldn’t look out of place in Brooklyn; it’s also the perfect place to work remotely if you can’t fully disconnect during your seaside retreat.

85 Rte. 6A, Orleans;

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Cape Cinema

Cape Cinema, Dennis

What to do with a rainy day on Cape Cod? Same as everywhere else: Go to the movies. But unlike everywhere else, the Cape has a 1930 art deco auditorium furnished with black lacquer and tangerine suede armchairs by the Frankl Galleries in New York. Along with screenings of indie, blockbuster and foreign films, the space hosts live music performances and occasional simulcasts of the Metropolitan Opera and Royal National Theatre. Perhaps the most striking feature of the building (which sits directly next to the famed Cape Playhouse, where actress Bette Davis once worked as an usher) is the vivid 6,400-square-foot ceiling mural depicting the heavens and constellations.

35 Hope Lane, Dennis;

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Encore Bistro & Bar/Facebook

Encore Bistro & Bar, Dennis

Nestled beside the Cape Cinema and Cape Playhouse, this quaint eatery is the perfect spot to grab a bite before or after a show. Elevate your evening with a reservation in the white-tablecloth main dining room or go the more casual route in the adjacent bar and tavern space. Don’t miss the garlic and clam flatbread, locally sourced Chatham mussels or lobster mango tower.

36 Hope Lane, Dennis;

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Sesuit Harbor Café/Facebook

Sesuit Harbor Café, Dennis

What’s a visit to the Cape without a lobster roll? This seaside shanty tucked into the Northside Marina (fun fact: Senator Ted Kennedy once kept his boat here) offers incredible views of the bay from its outdoor picnic tables. Home to arguably the best lobster roll on the Cape, the cash-only restaurant also boasts a raw bar and a BYOB policy. So pack a cooler and post up alongside the steady stream of boats gliding in and out of the adjacent harbor. If you prefer to actually get out on the water, the café offers cruises aboard its boat, aptly named The Lobster Roll. It departs the marina daily from June through September for sunset excursions with a dinner menu and full bar.

357 Sesuit Neck Rd., Dennis;

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Freewheel Cycles/Facebook

Freewheel Cycles & Rideaway Adventures, Mashpee

If you’re looking for an outdoor excursion but don’t feel like schlepping your own equipment on vacation, this full-service rental shop in Mashpee’s Popponesset Marketplace has you covered. Rent a bike, kayak or paddleboard and explore some of the area’s best trails and channels without hassle. If you did bring your two-wheeler and it suddenly needs service, Freewheel also offers mobile on-call repairs throughout the Cape, which means you’ll be cruising again in no time.

259 Shore Dr., Mashpee;

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Cape Cod Cultural Center

Cape Cod Cultural Center, Yarmouth

Located in a former 1930s bank (the building’s imposing ground-floor vault now displays art), this multi-use cultural space has a year-round program of BYOB concerts, gallery exhibits, lectures and activities. This fall the Cultural Center welcomes singer Antonia Bennett (daughter of Tony) as well as an Italian-inspired weekend in November that will offer on-site cooking and oil-painting classes.

307 Old Main St., Yarmouth;