Ten Great Things to do on Martha’s Vineyard

Jumping off the bridge at State Beach, Oak Bluffs, Martha's Vineyard. Max Hartshorne photos.
Jumping off the bridge at State Beach, Oak Bluffs, Martha’s Vineyard. Max Hartshorne photos

By Shannon Broderick

In 101 Things to Do in Martha’s Vineyard, Gary J. Sikorski gives travelers 101 reasons to hop on a ferry headed to Massachusetts’s star-studded vacation destination. From breathtaking cliffs to beautiful beaches, the Vineyard is full of beautiful views and fun activities.

Sea captain's houses on South Water Street in Edgartown.
Sea captain’s houses on South Water Street in Edgartown.

Sikorski is a freelance photographer and restauranteur who has worked in the tourist-related industry on Martha’s Vineyard and Cape Cod for several decades.

Here is a sample of some of Sikorski’s recommendations.

#10. Listen to live local music at clubs and restaurants in Edgartown or Oak Bluffs

If you still have some energy left for live entertainment after spending your day in the hot sun, you’ve got lots of nighttime options. National and local rock, reggae, rap and electronic bands pack in the summer crowds from Edgartown to Oak Bluffs. One of the local favorite spots is the Rare Duck Lounge, located right beneath the Lampost Bar. There is live music here from May through October.

Tip: Check out the listings in the MV Times to find out what’s currently happening at the Lampost and all over the island.

#9. Take a walking tour of the old dignified whaling captains’ mansions along the harbor in Edgartown

During the 1880s, Edgartown was a prime port for whaling vessels, and many of the successful whaling captains stayed and built these stately, white-clapboard homes facing Edgartown Harbor. Hundreds of these Federal-style mansions, complete with adorning white picket fences, line both sides of many of the streets in town. Take a walk down North or South Water streets to see the best selection of these immaculately kept grand structures.

#8. Go for a sunset sail on the ocean aboard the Mad Max catamaran

Sit back, sip on a cool beverage, and pretend you are one of the Kennedys aboard this beautiful sixty-foot, twin-hull catamaran. Departing right behind the Seafood Shanty on historic Edgartown Harbor, this state-of-the-art sailing vessel glides past the grand whaling ship captains’ mansions, the Edgartown Lighthouse, and Chappaquiddick Island. The sunset sail departs at 6 PM daily.

Mad Max charter sailboat, out of Edgartown for sunset cruises.
Mad Max charter sailboat, out of Edgartown for sunset cruises.

Tip: It’s B.Y.O.B, so grab yourself a little something to drink before you board.

#7. Rent a bike in Oak Bluffs, and ride the six-mile bike path along the ocean to Edgartown
The most popular bike ride on the island is this winding six-mile path that leads from Oak Bluffs to Edgartown. There are sweeping ocean views on one side and lush marshlands surrounding Sengekontacket Pond on the other. It’s a very scenic ride, but you’ll be sharing the path with walkers, runners, and inline skaters, so use caution and keep your eyes on the road.

Tip: So as not to backtrack on your return trip, take Edgartown-Vineyard Haven Road to County Road to Wing Road up to Oak Bluffs. It’s inland, so it’s not as scenic, but it makes for a nice change of pace.

Oak Bluffs Harbor bars and cafes, great people and boat watching.
Oak Bluffs Harbor bars and cafes, great people, and boat watching.

#6. Check out the artful creations at the Field Gallery & Sculpture Garden in West Tisbury
Established in 1970, The Field Gallery is another one of the must-see “things to do” on Martha’s Vineyard. Inside the gallery are three spaces with rotating exhibits, while the outside is home to dancing bronze sculptures and whimsical resin statues created by gallery founder Thomas Maley. The gallery is located right across the street from Alley’s General Store.

Tip: Check out one of the artist’s receptions held every Sunday afternoon in the summertime.

#5. Hang out at the bars and restaurants overlooking the boats in the harbor at the Oak Bluffs Dockside Marketplace & Marina

The heartbeat of the waterfront action on the island can be found up and down the boardwalk that surrounds this popular, active marketplace harbor. Beautifully scenic and bustlingly busy both day and night, there are dozens of open-air bars and restaurants with sunny porches that are always crowded.

The Oak Bluffs Marina is a great place for old and young alike to ogle the sailboats and the yachts docked in and along the harbor. Belly up to a bar stool, order up some raw bar favorites and enjoy the views. It’s a great place to people watch as well!

#4. Look in awe at the more than 30,000 items in the Martha’s Vineyard Museum

Tucked away on the corner of Cooke and School Streets in a residential neighborhood in Edgartown is Martha’s Vineyard’s historical museum. More than just a museum, this facility features outdoor exhibits, a reference library, and the remarkably preserved eighteenth-century Cooke Family House. Spend an afternoon and really get to know the island, historically speaking.

#3. Join the crowd jumping off the wooden drawbridge into the water at State Beach

Step atop the railing along the wooden drawbridge at the Joseph A. Sylvia State Beach, and your heart has to be pounding. It sure does seem like a long way down to the water.

But it’s packed with kids lining up all summer long to get their chance to perform an outrageous jump. This famous bridge, also know as the American Legion Bridge, is right on Beach Road and yes, you do recognize it from the movie Jaws.

Enjoying a lobster feed at Dutcher dock, Menemsha harbor.
Enjoying a lobster feed at Dutcher dock, Menemsha harbor.

Tip: The island bus stops here!

#2. Hike the scenic clay cliffs of Aquinnah, a.k.a Gay Head Cliffs

These epic, brilliantly colored clay cliffs are one of the island’s major attractions, and rightfully so. They were formed millions of years ago by glaciers and are now part of the Wampanoag Reservation and under special environmental protections to deter erosion. They are located on the western-most part of the island, making it a long trek out there–about an hour on the bus from Oak Bluffs–but it is time well spent.

Tip: Walk down to the beach parking lot, then take the worn path that leads down to the beach where you will be rewarded with spectacular (and the best!) views of the towering clay cliffs from sea levels.

#1. A must-do: get a steamed lobster at Larsen’s Fish Market then watch the sunset on the beach in Menemsha.

If you travel to Martha’s Vineyard and don’t get a steamed lobster and watch the sunset on the beach in Menemsha, you blew it! This is my many accounts the #1 thing to do on the island. You’ll need to call ahead to reserve your sunset lobsters, scallops, chowder and steamers. Don’t forget the melted butter. Then walk down the street, spread out a blanket or some beach chairs, and watch the sunset on the beach. Unforgettable!

Buy the book on Amazon here.

Sikorski's book provides readers with plenty of recommendations for fun activities to do on the Vineyard, both for new visitors and regulars.

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