There are a million reasons why we return, of course, but in 2021, these are the 23 that are making us pack up the car right now and head south. See you over the bridge.
Edited by Brittany Jasnoff
Maybe you’ve had a beach cottage in your family for generations. Maybe you’ve been renting the same place for the same two weeks since your kids were in preschool. Maybe you just book little getaways here and there to watch the sun sink into Cape Cod Bay. No matter how you get your Cape and Islands fix, one thing’s for certain: You (and countless other Bostonians) always come back, year after year. It’s the memories, of course—that indescribable feeling of eating fried clams from the same picnic table every summer. But it’s also the excitement of discovering something new in a place that has stayed by and large the same for decades—that fantastic new doughnut shop that’s so popular it needs its own traffic detail, or that hip new glamping destination that feels just rustic enough. There are a million reasons why we return, of course, but in 2021, these are the 23 that are making us pack up the car right now and head south. See you over the bridge.
1. Because getting a room just got a lot cooler.
From Airstream glamping to charming inns, four new ways to check in this summer.
The Intel: Historical sites, year-round restaurants, and more than 50 acres of nature trails are mere steps from your front door at this stately 1716 manse, which reopens this month under new ownership. Beaches are a short drive away, but why use the car at all when there’s so much right at your fingertips?
Best Room to Book: The hotel’s fully remodeled Carriage House is well suited to family reunions and bridal parties.
Don’t Miss: A visit to the late author and illustrator Edward Gorey’s house, which is literally right next door.
The Intel: 1920s Parisian salon meets 19th-century sea captain’s abode at this glam new Blue Flag Partners hotel, comprised of four adjacent inns in the heart of town.
Best Room to Book: Stretch out in the light-filled Manor House deluxe king room, where the property’s high ceilings, wood floors, and original architectural details are on full display.
Don’t Miss: Sister Ship, the hotel’s 140-seat indoor/outdoor resto-bar, is the place to see and be seen this season.
AutoCamp Cape Cod
The Intel: Commune with the outdoors (without sacrificing creature comforts) at this California-based glamping group’s first East Coast outpost, conveniently located just 15 minutes from the Bourne Bridge.
Best Room to Book: Families will love the “Basecamp” option, which includes a kitted-out Airstream for grownups and an adjacent tent so kids can sleep outdoors (but still close by). Taller guests might want to book a “Vista X Suite,” which has higher ceilings and more space to move around.
Don’t Miss: Cruising on the Shining Sea Bikeway, courtesy of AutoCamp’s gratis bikes.
The Edgartown Inn
The Intel: Lark Hotels continues its spree of scooping up historical Vineyard buildings with the Edgartown Inn, its fifth property. As a departure from other hotels you’ll find nearby, the farmhouse-chic space takes its design cues from the island’s agrarian interior—no shiplap in sight.
Best Room To Book: Opt for a deluxe king room with a balcony on the third floor and you’ll be treated to glimpses of the water as well as unparalleled people-watching on North Water Street.
Don’t Miss: The complimentary small-plates breakfast, including a delicious chia pudding and baked eggs. —Todd Plummer
2. Because relaxation is just a swipe away.
Why trek across island to go to a spa when you can have the spa come to you? Just in time for summer, the beloved Nantucket holistic healing center Lavender Farm Wellness has released an eponymous app that founder Brandon Jellison calls the OpenTable of wellness. Massage therapists, private yoga instructors, reflexologists, and even Ayurvedic chefs can be booked through the app for one-on-one sessions from the comfort of your own home or rental, from the provider’s studio, or from Lavender Farm HQ. “It’s a way for people to truly DIY their own wellness retreat,” Jellison says. —T.P.
3. Because where else can you spot the Obamas and Spike Lee?
Sure, it’s a great town with charming candy-colored cottages, a rich Black tradition, and a kick-ass carousel, but Oak Bluffs has also become a major beacon for celebs. Spike Lee owns a house there and is a devotee of Mocha Mott’s coffee shop, and at any given cocktail party, you stand a chance of running into intellectual notables such as Skip Gates. Obama senior adviser Valerie Jarrett, meanwhile, can often be found holding court at OB favorite Nancy’s. While the Obamas themselves might have bought in Edgartown, daughter Sasha worked the takeout window at Nancy’s as a kid—and who knows? Maybe you’ll spot them enjoying some fried oysters there when you visit. —Jonathan Soroff
4. Because it’s party time in P-town (At last!)
Provincetown has been many things to many people over the years, but it is perhaps proudest of its designation as one of the top LGBTQ destinations in the world. That’s a title, says Province-town Business Guild executive director Bob Sanborn, that the town is hoping to reclaim after a year spent laying low. This summer, party central is relaunching annual themed events such as Provincetown Pride (June 4 to 6) as well as Independence Week, Bear Week, Girl Splash, and Province-town Carnival, all of which will feature brunches, bingo nights, and cabarets hosted by P-town’s new drag-queen tourism ambassadors. Planning on making the trip? Here’s what you can’t miss this summer.
With Provincetown’s expanded outdoor food licenses extended for the 2021 season, expect a series of relaxed al fresco options from restaurants and cafés all across town. Favorites include the Canteen, known for its hot and cold lobster rolls, street corn, and beachy vibe, and Sal’s Place, a 59-year-old institution that recently started a “Sal’s Place at Your Place” takeout box complete with cloth napkins and flowers.
P-town’s cultural institutions are packing in the fun this summer. Running June 16 to 25, the Provincetown Film Festival features a screening of Being BeBe, the documentary that follows 15 years in the life of BeBe Zahara Benet, the first winner of RuPaul’s Drag Race. In the mood for a little live theater? The Provincetown Theater is setting up an outdoor “Parking Lot Playhouse” in July and August for its first in-person shows since 2019. And P-town’s entertainment central, the Crown & Anchor, will be hosting a mix of drag shows and musical acts poolside: Expect performances from Divas by the Sea Drag Bunch and Thirsty Burlington, among others.
Looking to actually sleep on your visit? Rest easy at the Awol. Located along the West End moors, it offers a fresh, modern setting with plenty of plush amenities (hello, fire pits and beach cruisers) that complement the natural beauty around it. —Gabrielle de Papp
5. Because it pays to shop local.
Whole Foods has nothing on these fabulous food purveyors.
Nauset Farms, Orleans
What It’s Like: A one-stop shop for gourmet foods, you’ll find everything from lobster bakes in a bag to potpies and picnic lunches here. (And if you hunt, the staff will even dress your wild game for you.)
House Specialties: Meat for the grill, including marinated kebobs and sausages, as well as a dessert selection that pays homage to Parisian patisseries.
The Chatham Cheese Company, Chatham
What It’s Like: You’ve got the beach house with a killer view—now you just need the right wine and cheese to help wash down those summer sunsets at the end of the day. Lean on personal chef and fromage expert Heather Cantin, who hosts tastings, offers advice on creating the perfect charcuterie board, and helps customers select the right wine to pair with it all from her carefully edited selection.
House Specialties: Cantin’s signature macaroni and cheese, as well as specialty sandwiches such as the Blue and Bee—Gorgonzola dolce, fresh apple slices, and a drizzle of local honey.
Chatham Bars Inn Farm Stand, Brewster
What It’s Like: Looking to re-create the magic from your favorite Chatham Bars Inn meal at home? Simply visit the farm where the five-star resort grows produce for its restaurants (or order online for same-day curbside pickup).
House Specialties: Seasonal vegetables such as radishes, mushrooms, and potatoes; honey from the onsite beehive; and fresh-cut flowers. —G.D.P
6. Because baseball’s best tradition is back.
Families sitting on metal bleachers practically right on the field, chowing down on hot dogs, soda, and Hoodsie cups. Dads playing catch with their kids along the third base line. At Cape Cod Baseball League games—returning this month after taking a COVID-induced break in 2020—it’s like the Fourth of July every day, except here, the fireworks come off the future stars’ bats. —B.J.
7. Because biking with a rum swizzle is better than driving
Gone are the days of sparring for cabs after a night at the Chicken Box, or missing your dinner reservation at Galley Beach because you’re stuck in Nantucket’s notorious traffic. This summer marks the debut of Sandy Pedals, the island’s very first bike-share program. With some 46 stations sprinkled around town, there’s no longer a need to rely on unreliable taxi services or pricey traditional bike rentals: Instead, you can either pay as you go at 25 cents per minute, or purchase a $125 unlimited monthly pass. “The whole gist is to reduce traffic and reduce emissions on island,” says founder and Nantucket resident Thomas Holt. Bonus points for making it easier than ever to enjoy a Madaket sunset. —T.P.
8. Because Jaws is only a movie…
Sure you can ride a roller coaster or bike down a mountainside, but is there anything more thrilling than coming face-to-face with an apex predator? Although great white sharks increasingly love to summer on the Cape, there still isn’t much reason to fear—despite the newsflashes and numerous beach closures you’ll see in the area whenever people spot fins from shore, there were only 57 unprovoked shark bites worldwide last year, none of which were in Massachusetts, according to the Florida Museum of Natural History’s International Shark Attack File. If those odds sound good to you, consider chartering a ride with Monomoy Sportfishing, which offers a “camera-only shark hunt.” The guides work in tandem with a professional spotter plane to steer you in the right direction, and while they don’t technically promise a shark sighting, they do claim to have a 97 percent success rate for eyeing those telltale fins. —T.P.
9. …But it still provides plenty of thrills from the comfort of your car.
If Spielberg’s take on sharks is a little more your speed, try pulling up to the old-school Yarmouth Drive-In or Wellfleet Drive-In Theatre, both of which screen Jaws several times throughout the summer in addition to other films. The outing promises to be so popular with your crew, it’ll have them saying, “We’re gonna need a bigger SUV” in no time. —T.P.
10. Because lush lawns aren’t the only grass on Nantucket now.
Bathing suit? Check. Overnight bag? Check. Legally purchased pre-rolled joint? Uh-oh. Nothing blows the high of planning a Nantucket getaway like the federal laws prohibiting the transfer of pot by air and sea. But fear not, green traveler, because the recently opened Green Lady Dispensary now grows, processes, and sells its own cannabis products all in one facility. That means now you can enjoy pre-rolls, delightful edibles, and vaporizers while on the island— then bring home a “Green Lady” T-shirt as a (legal) souvenir. —T.P.
11. Because the Kream ‘n Kone is still here.
I still remember the first time I spotted the Kream ‘n Kone. I was a college kid on one of my first trips down the Cape when I saw the old-fashioned sign boasting “the finest fried seafood anywhere” from the backseat of my friend’s rickety old Toyota Camry while cruising down Route 28 in West Dennis. Given that I’d already been in the car for an hour and a half and my stomach was growling louder than a truck motor, I begged her to stop so we could grab a quick bite.
The interior was not, even by a college student’s standards, impressive, with an old-school menu board and cafeteria-style food trays. Being from the mid-Atlantic, I wasn’t yet familiar with the idea of a classic New England clam shack, and I wasn’t expecting much when I ordered the fish and chips. But one bite of crisp, flaky haddock and thin-cut fries dunked in tartar, and I was hooked. I ordered a soft-serve vanilla cone to top it off (presumably the “kream” part of the name) and felt like I’d already arrived at the beach.
Of course, whether the Kream ‘n Kone actually has the finest fried seafood on the Cape is up for debate. In a world gone mad, though, I think we’re all really lucky that after nearly 70 years, it’s still there, bringing us the briny, salty joy of the ocean, one fried-clam dinner at a time. —B.J.
12. Because dining out this summer is more than just a meal.
Captain Baker Donut Shop, West Dennis
Owner Lauren Rengucci has painstakingly turned a former antiques shop into one of the best doughnut stands on the Cape—it’s so good, in fact, that a police detail is often called in to help with crowd control. Design your own ring with toppings, glazes, and drizzles, or keep it simple with an old-fashioned cinnamon.
Tree House Brewing Company, Sandwich
What goes better with a beer than ocean breezes? Nothing, that’s what. The panoramic deck at this brand-new beachfront taproom from cult-favorite Charlton brewery Tree House will be one of the Cape’s hottest spots to throw back a tall frosty one this summer.
Goldie’s Rotisserie, Martha’s Vineyard
Known for catering the Vineyard’s most exclusive parties, chef Lexie Roth—daughter of guitar legend Arlen Roth—brings her talents to a new arena this summer: a roving food truck serving up free-range, French-style rotisserie chicken. Be sure to order a side of schmaltzy potatoes drizzled with chicken drippings and crunchy sea salt.
The Front Lawn at Ocean Edge, Brewster
This al fresco experience on Ocean Edge’s expansive grounds returns for the second summer, offering tasty lobster sliders and wood-fired brick-oven pizzas brought straight to your lounge chair.
The Club Car, Nantucket
Thanks to a brand-new chef, the food at this iconic island nightspot—from skillet shrimp to a rib-eye for two—will be just as much of an attraction as the late-night scene this season.
Chatham Bars Inn, Chatham
The Cape’s most glamorous hotel adapted to the pandemic last year by offering its famed lobster rolls in a picnic basket to go. That service returns for hotel guests this summer, as well as an expanded Beach Bar menu so guests and non-guests alike can indulge in food and drink while relaxing on Chatham’s toniest stretch of sand. —T.P.
13. Because the second you cross the bridge, the tension begins to melt away.
The smell of salt air. The sound of the ocean and seagulls. The distinctive pitch pines. It’s the very embodiment of “Ahhh.” Upon reaching their destination, even the crankiest workaholics suddenly become beach bums, and the most helicopter-y of moms practically let their kids play in the middle of the street. There’s just something magical about the place. As the classic song goes, “If you’re fond of sand dunes and salty air….” —J.S.
14. Because clams and lobsters aren’t the only island foods we crave.
On the steamiest summer days, it’s easy to feel like you’re vacationing not on the Cape but a tropical island. And there are plenty of restaurants to reinforce that notion, thanks to a thriving Jamaican community in the area. Chef Shrimpy’s Jerk Café in South Yarmouth specializes in (you guessed it) jerk-style meats—don’t leave without taking home a bottle of his secret sauce chock-full of traditional Jamaican spices. Husband-and-wife team Cliff Harvey and Amelia Kisna-Harvey opened Eastham’s Brickhouse in 2018; now their coconut shrimp, orange rum scallops, jerk curry, and rum cake—a family recipe—are crowd favorites. Branches in Chatham, meanwhile, serves up a modern twist on Jamaican classics: Don’t miss the lemon-pepper shrimp and dirty rice with a side of plantains. —G.D.P.
15. Because the playgrounds here rock.
The Discovery Playground at Hinsdale Park
What it’s Like: As a STEAM-based playground, this park blends sensory play—thanks to optical illusion boards and musical games—with physical fitness, in the form of monkey bars, slides, and jumping courses.
Coolest Feature: “Everyday Science” signs that show visitors the mechanics behind the playground’s equipment and activities.
Village Science Playground
What it’s Like: In addition to the usual swings and slides, this nautical-themed play area highlights the region’s maritime history with seascape murals, a landbound wooden boat, and a small stage that resembles a nautical compass. There are also numbered plaques around the playground for kids to find, scavenger-hunt style.
Coolest Feature: A charming lighthouse replica that adventurous wee ones can summit.
Luke’s Love Boundless Playground
What it’s Like: An inclusive play space for kids with and without disabilities, this fenced-in park featuring music stations, ramps, and colorful play boards with buttons to press was improved and expanded during a two-year renovation completed in 2019.
Coolest Feature: Quiet zones under the slides for kiddos who tend to steer clear of loud environments. —Madeline Bilis
16. Because there are plenty of quirky, off-the-beaten-path activities.
Hunt for gnomes
You’ll find more than trees and plants at Polly Hill Arboretum in West Tisbury this year—if you know where to look, that is. Garden gnomes are in hiding, waiting to be discovered across the park’s 70 acres. Upon arrival, pluck a list of clues (written by an expert gnome spotter) out of the brochure box next to the visitor center, then see if you can find them all.
Smell the lavender
Reminiscent of the south of France, Cape Cod Lavender Farm in Harwich erupts in shades of purple and gold each summer. Swing by to see (and smell) the lavender harvest in its peak bloom period in late June and mid-July. Once you’ve followed the winding paths on its grounds, duck into the farm’s gift shop to peruse the very violet selection—the lavender-filled hair scrunchies are a favorite.
Visit the scene of an art heist
No, not that heist. Two years before the Isabella Stewart Gardner Museum was famously robbed, two thieves tied up the caretaker of the historical Captain Bangs Hallet House in Yarmouth and made off with 19th-century paintings, 200 pieces of scrimshaw, and other valuables. There’s a theory the theft is connected to the Gardner heist—and it is, in a way: Both cases remain unsolved.
Say “om” with alpacas
Yes, you read that right: Alpaca yoga is really a thing. Island Alpaca Company in Oak Bluffs introduced three new babies to the herd this spring, and in addition to patting their fuzzy heads and feeding them snacks, you can reserve a spot in an alpaca yoga class. For a slightly less hands-on experience, try a yarn-spinning course, or just shuffle home in a pair of alpaca fleece slippers. —M.B.
17. Because food trucks are the ultimate pop-up beach party.
Forget boring old hot dogs and chicken tenders: For the past few years, hungry sun worshipers on Orleans’ Nauset Beach have had a much more exciting option when the beach munchies strike. After a series of nor’easters in 2018 laid waste to Liam’s—a local snack shack renowned for its onion rings and summer concerts—the town of Orleans decided to create a designated food-truck area at the beach instead. This year, they’re back with a lineup that includes sweet treats from the Ice Cream Café, an Orleans institution, as well as savory sustenance from Capeside Kitchen Beach Patrol (wraps, sandwiches, all-day breakfast) and High Tide Burger Co. Roll out a towel, then roll up to the ordering window for the food of summer. —G.D.P.
18. Because everything’s more fun along the Cape Cod Rail Trail.
We don’t hop on the longest dedicated bike path in Massachusetts to put the pedal to the metal—we hop on to enjoy a leisurely ride with spectacular vistas from Yarmouth all the way to Wellfleet. Oh, and to take a break at these prime spots along the way.
MILE 11.5 Swing by the old Pleasant Lake General Store, a.k.a. Pizza Shark Cape Cod, in Harwich to scoop up freshly made sandwiches and chips for a picnic (and some quarter-pound bags of penny candy for later—this is a vacation, after all).
MILE 16 It’s just a few more miles to Nickerson State Park, where you can cool off with a dip in a kettle pond before enjoying your repast in a shady grove.
MILE 17.5 Continue on to Orleans and pause for a thirst-quenching Outermost IPA or Far Out Stout (and maybe a little live music) at Hog Island Beer Co.
MILE 22 Stop by the Cape Cod National Seashore Salt Pond Visitor Center in Eastham to marvel at the salt marsh and check out the museum, which includes an Indigenous village, a whaling skiff, and a spectacular collection of scrimshaw.
MILE 27.5 The trail ends in Wellfleet, where you can reward yourself by slurping back a few bivalves on the Wicked Oyster’s patio before catching a ride home. —J.S.
19. Because science lessons go down better in a quaint seaside village.
If you’ve lived in New England for any amount of time, you know that cool, rainy June days happen—and when you have impatient kiddos, it always pays to have a backup beach plan. That’s where Woods Hole—for years a mecca for marine science research—comes in. While the village’s free aquarium and its much-loved touch tanks remain closed due to COVID, the Ocean Science Discovery Center is reopening just in time for summer exploration. The little ones will love checking out the REMUS SharkCam, as well as an interactive display about the discovery of the Titanic, and a new exhibit (coming in late June) about the bioluminescent creatures found in the Ocean Twilight Zone—and you’ll love the center’s brand-new touchscreen stylus pens so they can stay germ-free. —B.J.
20. Because playing in the surf is way More Interesting than looking at it.
Must-try water sports for every kind of thrill-seeker.
Who among us has never longed for the power of flight? Now, on the Vineyard, your wish can come true. Part skateboard and part jetpack, flyboards are actually made using the steering nozzle from a Jet Ski attached to a fire hose, which shoots out streams of water that propel you through the air. Martha’s Vineyard Ocean Sports is one of the only companies in Massachusetts to offer flyboarding lessons, starting at $120 per session—superhero cape not included.
Next time you’re on Nantucket, dive into the latest water-sports craze: eFoiling, which lets you glide above the water thanks to a battery-powered surfboard. As it turns out, the placid waters and sheltered bays of Nantucket Harbor are uniquely suited to this surfing upgrade. The experts at Next Level Watersports will ride alongside you in a boat, providing instruction as you cruise ahead.
Consistent breezes off Nantucket Sound make the Cape an excellent place to try windsurfing, and the pros at Wellfleet’s Fun Seekers have been introducing beginners to the sport since 1985. First-timers can start off gently at Gull Pond, while more experienced students are taken to Cape Cod Bay at Indian Neck Beach. Though the guides can’t guarantee you’ll be shredding the gnar and navigating gale-force winds from the get-go, they do promise to get you up and sailing with just one introductory lesson. —T.P.
21. Because buying a summer home is hotter than ever.
Been dreaming about escaping to the Cape for the past 15 months? You’re not alone. As hordes of Bostonians (and—cringe—some New Yorkers, too) continue to hunt for a place to spend their WFH days relishing the fresh salt air, demand for housing in the area has rocketed through the stratosphere. The median home price in Falmouth, for example, increased by 19 percent in 2020. In P-town, it shot up by a whopping 24 percent. And the town of Barnstable was the fourth-most-popular place to move in the country. “We’ve had rapid appreciation in the past, but probably not as rapid as this is,” says Bernie Klotz, a Cape-based broker associate with Kinlin Grover Real Estate. “On top of that, we’ve never had bidding wars here. And we are now having those.” If you’ve already scored your slice of paradise, sit back, relax, and enjoy it. And if not? Well, there’s always next year. —B.J.
22. Because there’s plenty of life on the other side of the Cape Cod Canal, too.
For those times when sunburn or lousy weather rule out the beach, try one of these quick day trips.
Edaville Family Theme Park, Carver
What’s one thing the Cape doesn’t have? A Jersey Shore–like amusement park. Luckily for the kids, there’s one less than 20 minutes from the Bourne Bridge. What started out as a narrow-gauge railroad through a series of cranberry bogs now has an area devoted to Thomas the Tank Engine, a dinosaur-themed section with 23 life-size animatronic models, and rides that include a Ferris wheel and tilt-a-whirl. And what’s not to love about a spinning Ladybug coaster at the height of summer?
Myles Standish State Forest, Carver
If the nature trails on the Cape are overrun with annoying hordes of tourists, try this superb alternative in Plymouth County. An underappreciated outdoorsman’s dream, it offers 13 miles of trails and 35 miles of bridle paths for equestrians. Kettle ponds and pine barrens make up one of the prettiest landscapes in New England, and you can end your visit with a dip in College Pond.
The South Coast Vineyards
Who says good wine only comes from Napa? The fertile soil along the New England coast actually makes for ideal grape-growing conditions—including on the South Coast of Massachusetts, where you’ll find a handful of spots to tour, from Running Brook Vineyard & Winery in Dartmouth to Westport Rivers Winery, known for its sparkling vinos. We’ll drink to that. —J.S.
23. Because there’s no better place to get lost.
Ditch the Sand for the day and get moving on these four breathtaking hikes.
Pleasant Bay Woodlands, East Harwich
What to Expect: See a new part of the Cape this year thanks to the Harwich Conservation Trust, which recently debuted walking trails at Pleasant Bay Woodlands that protect some 50 acres of watershed landscape. Rolling hills make for a gentle milelong walk that curves through the trees.
Keep an Eye Out For: Bird species such as red-bellied woodpeckers and eastern bluebirds.
Middle Moors, Nantucket
What to Expect: Bring a hat and sunscreen—there’s no shade cover in the Middle Moors, the largest stretch of undeveloped land on the island. The former sheep-grazing pastures are a wonder in their own right, but you’ll want to take the trail toward Altar Rock for panoramic views of the ocean and several lighthouses.
Keep an Eye Out For: Species of asters, goldenrods, and other wildflowers throughout the summer and fall, plus some blueberry bushes.
Nauset Marsh, Eastham
What to Expect: The trail begins behind the Salt Pond Visitor Center; take it to hike an easy 1.3 miles beside a kettle pond and then over a small bridge, which opens to stunning views of Nauset Marsh.
Keep an Eye Out For: Two particularly fragrant plants growing beside the trails: salt spray roses and bayberry.
Atlantic White Cedar Swamp, South Wellfleet
What to Expect: Late last summer, the Atlantic White Cedar Swamp trail reopened after parts of its wooden boardwalk and seating areas were replaced. Now you can walk freely along the planks that wind through a grove of white cedar trees.
Keep an Eye Out For: In addition to white cedars, try to spot the black and white oak trees, as well as red maples—and don’t forget to snap photos of the curvy, Dr. Seuss–like pitch pines flanking the trailhead. —M.B.