Where to Eat, Stay, and Play on Cape Cod

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From afar, Cape Cod looks like one of many New England summer vacation destinations. But zoom in and it’s so many different, wonderful pieces. It’s the land of eccentric ice cream scoops heaped on fresh, buttery waffle cones. It’s the ecologically fragile peninsula where seals flop on tidal flats, whales come up for air, and bats swoop overhead. It’s a confluence of cranberry bogs, marshy lime green wetlands, and scrubby dunes. And though it’s a favorite summertime spot, it is just as nice off-season. It’s also 70 miles long so it’s best to break it into three regions—and to make more than a single trip so you can explore it all. The names for the regions can be confusing: Only in Massachusetts would the “Upper” actually be south of the “Lower,” so bear with us. Here is our guide for what to do in Cape Cod: where to eat, stay, and play.

Editor’s note: Due to ever-changing COVID-19 restrictions, visitors are advised to contact businesses directly for updated hours and safety guidelines. Advanced reservations are recommended.

Upper Cape

Towns of Sandwich, Bourne, Falmouth, Mashpee

Stay here if: You’re staying for one night—it’s only an hour from Boston and provides all the old school Cape eats and entertainment.

Where to eat

With live piano, regulars, New England clam chowder, and harbor views the Chart Room in Cataumet is an institution. For lunch, the must-order is the lobster salad, stuffed, and overflowing in an enormous tomato like some luxurious coastal Panera bread bowl. For dinner, it’s the baked stuffed lobster. The drink to order is the mudslide. Yes, that Mudslide: a blend of Bailey’s, vodka, kahlua, and lots of ice. Look around and everyone has one in hand—it’s a tradition. For a lobster roll en route to Surf Drive beach, swing by the Barking Claw, a seasonal stand which serves generous amounts of tail, knuckle, and claw meat Connecticut-style—that’s drizzled in hot melted butter, never mayo. Naturally, the bread is a New England hot dog bun, which means it griddles superiorly thanks to its flat cut sides. For a night of beer and artisan thin crust pizza, visit Bad Martha’s Falmouth Brewery (their original Martha’s Vineyard location is open seasonally). They have a rotating selection of at least 16 of their own beers on tap at any given time. Also on offer during the pandemic is beer to-go, which can be ordered online as four-packs or growler refills.

Where to stay

After a total redesign and renovation in 2018, the Coonamessett Inn (from $119 a night) in Falmouth remains a stalwart of old Cape Cod, but now with a modern touch—in-room USB chargers, smart TVs, and more. The hotel is a known wedding venue, but there’s no need to wait for a special occasion to spend a night. The rooms, with decor that includes knotty pine, iron frame beds, shiplap, lacy wallpaper, and more coastal elements, are tempting enoug, as is the on-site restaurant, Eli’s Tavern, where you can find scallop casserole with beurre blanc and their famous huge slices of carrot cake.

What to do

Go biking with the whole family along the 10.7-mile Shining Sea Bikeway in Falmouth that stretches from North Falmouth to Woods Hole. The trail name references a lyric from “America the Beautiful,” by Katherine Lee Bates, who was a Falmouth resident. Along the way, pass through a cranberry bog, spot horse crossing signs, spy the back of Bourne Farm, and take in Sippewissett Salt Marsh before making a pit stop at Surf Drive Beach. The terrain is flat, paved, safe, and doable for kids of all ages. Veer off at the end to check out Nobska Lighthouse, where you can find more on Katherine Lee Bates along with sweeping views of Vineyard Sound.

Mid Cape

Towns of Barnstable, Dennis, and Yarmouth

Stay here if: You want to be in a convenient commercial hub and have easy access to all the other parts of the Cape (as well as Martha’s Vineyard and Nantucket).

Where to stay

Dreaming of having a Cape house totally to yourself, with grey weathered shingles, white trim, wicker chairs, and your very own deck to sip coffee on in the mornings? Airbnb has a very good one in this one-bed, one-bath loft in the heart of Barnstable ($120 a night).

Where to eat

Remember that ice cream we mentioned up top? Here it is at the Cape Cod Creamery. The homemade hard ice cream comes in myriad flavors including Almond Joy, ginger, pistachio, heath bar, and bananas foster. Whatever flavor you choose, do not under any circumstances, forgo the waffle cone as its vessel. Soups and subs are also on the menu. There is a location in Hyannis as well as South Yarmouth. During the high season, swing by the seafood shack Sesuit Harbor Café in Dennis to snack on golden, crispy, briny fried littlenecks on a picnic bench overlooking the water on your way back from the beach.

What to do

Take a break from the beach and lobster and geek out on some history. You may not be able to scope out the Kennedy compound in Hyannis Port, six acres of waterfront property along Nantucket Sound where the family spent their summers and Ethel Kennedy still lives, but you can learn about the Kennedys’ connection to the Cape at the nearby Kennedy Museum. It reopens for the season on April 15—however private tours can be scheduled even while the museum is closed.

Lower Cape & Outer Cape

Towns of Brewster, Chatham, Harwich, Orleans, Eastham, Wellfleet, Truro, and Provincetown at the end

Stay here if: Secluded natural environments or the progressive community in Provincetown are what you seek on your trip.

Where to stay

The Mansion at Ocean Edge Resort and Golf Club (from $205 a night) in Brewster is a luxe stay with nine tennis courts, five pools, bike rentals with access to the Cape Cod Rail Trail, kayaking, paddleboarding, oyster bed tours, and its own beach. Its sister resort, the Villages at Ocean Edge Resort, (from $119 a night) shares the grounds and offers more private accommodations. The Beachfront compound of the Chatham Bars Inn (from $290 a night) has rooms and cottages that manage to be both luxurious and quintessentially Cape Cod (and super dog friendly). It also has special happenings, like a Friday night art series with local artists and gallery owners as well as a whole range of top-notch restaurants onsite (more on that below).

Where to eat

Whether you’re staying at the Chatham Bars or not, Stars, the hotel’s main restaurant, is a break from all the lobster shacks. The splurge spot has plenty of chilled shellfish and serious entrees like lobster fra diavolo and a tomahawk steak for two. During COVID-19, a new way to dine is available at the hotel, curbside pickup, with more casual items such as a dry-aged burger, crab cake sandwich, and a family-style apple crisp. Another new option is private dining.

What to do

There’s no time like the winter, spring, or a rainy day to gallery hop in Provincetown. The Rice-Polak Gallery features the work of mid-career and emerging artists alike, group and solo exhibitions, and contemporary art in an array of media including photography, sculpture, and digital art among the paintings. Cortile Gallery is another gem that’s worth browsing even if not shopping. When not impacted by a global pandemic, Provincetown also has great nightlife, whether you’re looking to see a cabaret show or check out the local theater scene.

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