Best Things to Do in Martha’s Vineyard

Surf’s up! You didn’t come all the way to an island to not check out its iconic beaches. Whether you’re keen to lie in the sand with an issue of Fifty Grande or take to the water for some aquatic shenanigans, the Vineyard has you covered with an array of beaches in all directions. Joseph Sylvia State Beach is one great option, equidistant between Edgartown and Oak Bluffs and boasting two miles of sandy shore. It’s perfect for a bike excursion between the two neighborhoods. (If you’re centered on the west side, head to Menemsha Public Beach instead.)

Due east of the grand island of Martha’s Vineyard lies yet another island, albeit one a bit more sequestered. Easily accessible by ferry, Chappaquiddick is for the nature diehards: think isolated beaches and hilly, tree-filled terrain. Bring your bike to traverse the island’s trails or a fishing pole to try your hand at catching everything from striped bass to bluefish. The surroundings also boast a quaint Japanese garden (Mytoi Japanese Garden) and a golf course (Royal and Ancient Chappaquiddick Links).

A local landmark, this big, white lighthouse screams New England charm. Steps away from its namesake harbor, this is the ideal spot to take a breather (and a picture) before or after the beach. The lighthouse is dedicated to children who have passed away, the names of whom are added on an annual basis.

Cue John Williams’ iconic theme song. Steven Spielberg’s classic “Jaws” was filmed all over the island in the ’70s, and is one of the community’s many claims to fame. The man-eating legend is still alive and well at what’s popularly referred to as Jaws Bridge, the filming location of one of the film’s numerous gruesome shark attacks. Today, tourists gawk and fish on the bridge, which is officially named American Legion Memorial Bridge. Just don’t jump off it, as some do: it’s not only life-threatening, but illegal.

Ladies and gentlemen, step right up to the oldest operating carousel in these United States! A National Historic Landmark dating back to the 1800s, legend has it the massive contraption was originally based in New York City before moving to the Vineyard community of Oak Bluffs. As a result, generations of children have rode around this piece of history, still humming along to the music of a Wurlitzer organ.

Imagine walking through what amounts to a fairy-tale village where characters like Hansel and Gretel would reside and putter around on their cute little jaunts. That’s the best descriptor for this neighborhood of tiny houses in the Oak Bluffs section of the island, which was originally built for local Methodists and today comprises around 300 colorful little homes all with their own vibrant personalities. A quaint on-site museum is there to tell you all you’d want to know.

It’s the kind of neighborhood bar that has local brews on tap, cold Bud Lights at the ready, the day’s games on the TV, lively music and good vibes. The Wharf is a staple where locals and tourists alike either laugh the night away or drown their sorrows. Better yet, the establishment has live music on certain nights, as well as an attached restaurant space with seafood-filled grub for lunch and dinner. Don’t forget to pack your dancing shoes and keep tabs on their calendar of live entertainment.

A classy part of the Vineyard food and beverage landscape for the past two decades, Alchemy is highly regarded as whipping up the best cocktails on the island, as well as having one of the area’s most respectable caches of wine. Aside from the aforementioned cocktails (including the Edgartown Old Fashioned made with housemade apple cider bitters), the food here is just as high quality, from dinner (local scallops) to dessert (pistachio cake).

Lobster, anyone? This partly outdoor seaside oasis-slash-shack is a classic New England coastal eatery, boasting scrumptious oceanic treats such as clams, steamers and quahogs, all in addition to delights like fried pickles and top-quality wings. But if you’re a fan of those aforementioned red steamy lobsters, make sure you visit on a Tuesday when you can feast on a bad boy for just 22 bucks. Top it off with a local beer and you have yourself a quintessential Vineyard meal.

What started as a local bakery that began giving away goods at day’s end to hungry high schoolers out their back door has evolved into a local legend. With the unique hours of 7 p.m. to midnight, Back Door Donuts serves high-quality confections that could soothe any sweet tooth. The star attraction here is an apple fritter, a tremendous hunk of deliciousness the size of your fist outfitted with chunks of fresh apple. It’s a Martha’s Vineyard icon worth the hype.

It’s not a true summer day without an ice-cold, creamy cone in hand. An endearing local chain, Mad Martha’s has been serving up homemade ice cream and sundaes on the island since 1971. From classic flavors to more inventive ones (like mud pie, MV sea salt caramel and Chilmark coffee, named after the western Vineyard community), its beloved trio of outposts can make any lip-smacking customer anything but mad.

It’s not often one can stay in an eye-popping hotel that’s been in continuous operation since 1879. Towering over the water like a castle in the community of Oak Bluffs, Summercamp stays true to its name; it’s designed as a place to both rest after a long day and to hang out in. With a colorfully Instagramable lobby replete with couches and a ping-pong table as well as a massive wraparound porch filled with cushy seats outside, the joyful atmosphere of a camp is on full display. Aside from airy, spacious rooms with waterfront views, the property also offers massive wooden lockers so you can stash your bags before and after checkin. Even better: free coffee and tea in the lobby, and a canteen that sells breakfast sandwiches and fresh biscuits.

Relax in sweet comfort at the very place where a young John F. Kennedy once checked in and chilled out. A quick jaunt away from the bustling community of Edgartown (and its shops, restaurants and beaches) lies Hob Knob, a quaint boutique hotel that exudes the homey vibes of a bed and breakfast. That includes expansive rooms, an on-site spa and yes, even an included, delectable breakfast made to order featuring crisp scones, fresh coffee and eggs any way you like ’em. First opened nearly a century ago, another highlight of the Hob Knob is its ample common spaces: a wraparound porch and multiple living and dining rooms perfect for recharging before or after your day on the Vineyard.