Things to Do on Martha’s Vineyard | Coastal Weekend Getaways

The Yankee Magazine editors share some of their favorite places to eat, favorite places to stay, and favorite things to do on Martha’s Vineyard.

By Yankee Magazine

Mar 18 2019


Aquinnah Cliffs | Things to Do on Martha’s Vineyard

Photo Credit : C. S. Imming/Wikimedia Commons
Alongside Block Island, Nantucket, and the Elizabeth Islands, Martha’s Vineyard rounds out southern New England’s collection of top-notch offshore destinations, with the Vineyard alone attracting thousands upon thousands of visitors — U.S. presidents included — each year. The Vineyard’s pristine shores, boasting warm sands and cool ocean waters, provide summer visitors with countless places to relax, swim, and take meandering coastal strolls. And the bustling seaside towns that grace the island have their own sort of charm, too, what with their barnacle-encrusted docks and elegant Cape Cod–style architecture. From the red clay cliffs of Aquinnah to the busy streets of Edgartown, here are some of our favorite things to do on Martha’s Vineyard, as well as a few of the island’s most popular places to dine and stay. SEE MORE: Coastal Weekend Getaways in New England | Your Perfect Weekend
Things to Do on Martha's Vineyard | Coastal Weekend Getaways
The ferry On Time III heads toward Chappaquiddick Island | Things to Do on Martha’s Vineyard
Photo Credit : Arwcheek/Wikimedia Commons


Menemsha Hills Reservation

Salt marshes, sandy cliffs, swaths of beach roses — these are the sights that attract visitors to the Menemsha Hills Reservation’s 221 acres and 3.2-mile walking trail. Wind your way through a forest of deciduous trees that quickly turns to pitch pine scrub, to dune grass, and finally to sandy cliffs and rocky shoreline. There, engulfed in the salty ocean breeze, you’ll find an uninterrupted view of the Elizabeth Islands from the second-highest point on the Vineyard, Prospect Hill. North Road, Chilmark. 508-693-3678; MORE: Walks Worth Their Salt | New England Ocean Walks

East Beach, Cape Poge Wildlife Refuge

Martha’s Vineyard has so many great beaches lining its shores, it’s hard to pick just one to highlight. That said, one of the island’s best strips of sand might be East Beach on Chappaquiddick, aka “Chappy” — the small, largely forested piece of land that shifts between a peninsula and an island, depending on the weather. Chappy’s on-again, off-again relationship with the Vineyard’s main island keeps the land remote, as does the Trustees of Reservations, which long ago secured much of Chappaquiddick for its conservation efforts. East Beach offers warm, soft sands and cool ocean waves perfect for bodysurfing, and parts of the beach are accessible to over-sand vehicles, too. Also worth mentioning is Mytoi, a beautiful Japanese garden just minutes from East Beach. Cape Poge Wildlife Refuge,Dike Road, Chappaquiddick Island. 508-627-7689;

Chilmark Chocolates

Delicious handmade confections are the hallmark of Chilmark Chocolates, the island’s premier chocolatier. Here a wide variety of chocolates can be found — each one better than the last. Limited opening hours and extremely popular products make Chilmark Chocolates a magnet for long lines, but the consensus among patrons is that the heavenly chocolates are more than worth the wait. 19 State Road, Chilmark. 508-645-3013
Aquinnah Cliffs | Things to Do on Martha's Vineyard
Aquinnah Cliffs | Things to Do on Martha’s Vineyard
Photo Credit : C. S. Imming/Wikimedia Commons

Aquinnah Cliffs

The famous Aquinnah Cliffs are a sight to behold, with their steep streaks of red and gray clay. Drive as far into Aquinnah as the pavement takes you, then park and walk the rest of the way, past the gift shops and restaurant, to the overlook, where you’ll enjoy a panoramic view of the cliffs, Gay Head Light, and the ocean. For a different perspective, make your way down to either Moshup or Aquinnah Beach, two public beaches that will let you get a little closer to the scenery. Aquinnah Circuit, Aquinnah. 


Art Cliff Diner

Rightfully considered an island icon, the Art Cliff Diner has been serving up some of the best breakfasts on the Vineyard since 1943. Tasty twists on favorite diner food classics make the tiny, vintage-themed restaurant occasionally see a line out its door — and for good reason. Needless to say, get there early! 38 Beach Road, Vineyard Haven. 508-693-1224;

Chilmark Tavern

Using a slew of locally grown ingredients, the Chilmark Tavern’s head chef, John Thurgood, creates an ever-changing menu of delicious, upscale dishes. Surf, turf, and greens galore, the restaurant’s recipes use only the best of the best. The Chilmark Tavern also offers takeout, meaning its top-notch cuisine can be enjoyed even in the comfort of your own home. 9 State Road, Chilmark. 508-645-9400; [text_ad]

Larsen’s Fish Market

Larsen’s Fish Market is located just minutes from the busy docks of Menemsha, a small fishing village on the Vineyard’s western shore. The village itself is packed in the summer months, when parking can be scarce, which is why Larsen’s dockside location makes it extra popular with boaters and fishermen. The market’s presence on the water is also reflected in the freshness of its seafood — and if you wait around long enough, you’re sure to see the latest catch arrive. Right beside Larsen’s you’ll find the Menemsha Fish Market, another great spot for fresh seafood. 56 Basin Road, Chilmark. 508-645-2680;

Martha’s Vineyard Chowder Company

Best known for its award-winning clam chowder, the Martha’s Vineyard Chowder Company is your quintessential seafood restaurant with a sleek, modern ambiance. You’ll find all the favorites here, like fish and chips, raw oysters, and a half-pound lobster roll, as well as an extensive list of cocktails and other drinks. The restaurant’s location couldn’t be better: minutes away from the ferry and across the street from the famous Flying Horses Carousel9 Oak Bluffs Ave., Oak Bluffs. 508-696-3000;

Mocha Mott’s

With locations in Oak Bluffs and Vineyard Haven, Mocha Mott’s is a must-visit for anyone wanting to experience some of the best coffee on the island. Get there early to grab a freshly delivered Cape Cod bagel or a homemade pastry, then indulge yourself in a cappuccino, espresso, or one of many other caffeine boosters. 15 Main St., Vineyard Haven, 508-693-3155; 10 Circuit Ave., Oak Bluffs, 508-696-1922.


Mansion House

Mansion House is conveniently located right at the end of Vineyard Haven’s lively Main Street, where restaurants and boutiques abound. Fantastic eateries and shops are just minutes away, as is the Vineyard Haven ferry. The inn’s rooms are clean and colorful, and some of them even feature balconies and fireplaces. Mansion House also boasts a spa and health club, making the decision to escape to the Vineyard for a weekend even easier. 9 Main St., Vineyard Haven. 508-693-2200;

Harbor View Hotel

A sunrise over busy Edgartown Harbor and its charming lighthouse is a sight to be seen from the Harbor View Hotel’s large wrap-around porch. The hotel occupies almost an entire block with its huge main building, dining areas, luxury cottages, and amenities, like the heated outdoor pool and gym. The Harbor View Hotel is just a short walk from the main streets of Edgartown, where you’ll find restaurants, galleries, and shops galore. 131 N. Water St., Edgartown. 508-627-7000;

Outermost Inn

Its location atop the beautiful Aquinnah cliffs gives the Outermost Inn unrivaled and uninterrupted views of the Vineyard Sound and Elizabeth Islands. The rooms are spacious and — thanks to large windows and a colorful palette — bright and welcoming. The inn’s intimate restaurant receives rave reviews and, unsurprisingly, requires reservations made well in advance. In the summer, enjoy a breathtaking sunset while relaxing in an Adirondack chair on the inn’s private lawn. 81 Lighthouse Road, Aquinnah. 508-645-3511; What are your favorite things to do on Martha’s Vineyard? Let us know in the comments!

SEE MORE: Coastal Weekend Getaways in New England | Your Perfect Weekend