Famous coast of Oak Bluffs Martha's Vineyard
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Things To Do

From Oak Bluffs to Edgartown, to the cliffs of Aquinnah and the beaches of Menemsha, Martha's Vineyard offers so much to do and see! Oak Bluffs is a funky, thriving hive of activity, and the perfect home base for your Martha’s Vineyard vacation.

Here are our suggestions for exploring Oak Bluffs and beyond:

1. Historic Oak Bluffs Gingerbread Cottages

Located right outside our front door, these boldly painted, ornately carved cottages were built by Methodist Church campers during the mid 1800’s. The Martha’s Vineyard Camp Meeting Association offers tours of the Campground every Tuesday and Thursday in July and August. The central Tabernacle is on the National Register of Historic Places and is still home to weekly church services and a host of cultural events throughout the summer.

2. Ride the Carousel

Be a child again on the Flying Horses Carousel. Housed in a dark red building near the Steamship Authority Oak Bluffs terminal and a close stroll from Summercamp, it’s the oldest operating platform carousel in America. Reach for the brass ring to win a free ride. 

3. Fishing and Boating Excursions

Plan Sea

Embark on a daytime cruise, set out to sea as the sun sets over the horizon, enjoy a one-of-a-kind bachelorette party, or witness a 4th of July fireworks show you’ll never forget––all possible aboard the Plan Sea. With the capacity for up to 22 passengers, this sea vessel offers indoor and outdoor seating, plus a wet bar and is sure you to leave you with memories of a lifetime.

Skipper

For an ocean fishing expedition on the protected waters of Vineyard Sound, we recommend the Skipper out of Oak Bluffs harbor.

Magic Carpet

Sailing daily (in season) from Edgartown's Memorial Wharf, the Magic Carpet is a gorgeous, classic 56’ wooden yawl. True sailing at its best, you’ll feel the splash of the sea as this beautiful boat comes about.

Mad Max

This massive catamaran offers two-hour smooth and graceful cruises around Edgartown harbor. 

4. Biking and Hiking

Martha’s Vineyard features miles of biking and hiking trails all over the Island. Hop on a bike and peddle the 14 miles round-trip along the water to Edgatown. For hiking, trek through the stunning scenery of the Martha’s Vineyard Land Bank, Sheriff’s Meadow, or Mass Audubon’s Felix Neck Wildlife Sanctuary. We’ll give you directions and tips.

5. Kayaking & Kiteboarding

Rent from Island Spirit Kayak and paddle your way through the island’s rich wildlife. Spy shellfish beds, ospreys and their nests and small islands inhabited by rare Piping Plovers. Or, paddle into the calm waters of Sengekontacket Pond to watch the kiteboarders lift off the water into flight. (Or for the really adventurous, try kiteboarding lessons yourself with Skyhigh Kiteboarding.)

6. Sunset in Menemsha 

Picnic in the party scene and waning light of Menemsha Beach at dusk. Impromptu jam sessions, volleyball games, and squealing children add to the atmosphere. Ask our guest services crew to call ahead to Larsen’s Fish Market to arrange a take-out New England Clambake of lobster, clams, corn on the cob, and all the fixin’s. (Menemsha)

7. Feed Your Sweet Tooth 

Trek to the little Chilmark cottage that houses one of the Island’s sweetest secrets. Chilmark Chocolates are highly addictive and only available at this tiny store and at a handful of other island locations. Sorry - no website. Queue up (there’s ALWAYS a line) and shuffle through to make your selections and assuage your inner raging chocoholic. (Chilmark)

8. Beaches for Every Occasion

Oak Bluffs Town Beach

Just off the town green, this gentle, shallow beach begins near the Steamship Authority dock and ends at Joseph Sylvia State Beach. 

Joseph Sylvia State Beach

Calm waters and plenty of sand space make this a gathering spot for many visitors. It’s an easy bike ride from Summercamp. Call on your inner movie buff and join the crowds jumping off “Jaws Bridge.” Search for sea glass along the water line.

Katama/South Beach

A bit further afield, this expansive and sprawling Atlantic Ocean beach is all about volleyball, romping in the tide and summer fun. Be careful in the water as the waves can get large and undertows are common.

9. Mytoi Japanese Gardens in Chappaquiddick

As the locals say, take the “on time ferry to Chappy” and discover the Mytoi Japanese Gardens. Winding footpaths guide you through a birch walk, camellia dell, stone garden, and hillside garden. A rustic shelter offers a broad view of this garden of exotic and native plantings that encircle a serene pond full of turtles, frogs, and goldfish.

10. Island Sightseeing Tour

Hit Martha’s Vineyard’s major highlights and learn a lot of island lore on the Martha’s Vineyard Sightseeing bus. The company offers a 2½-hour tour with a ½-hour stop at the Aquinnah Cliffs and Gay Head Lighthouse. The cliffs are a protected National Historic Landmark and clay bricks excavated from the site were used in constructing the lighthouse. We highly recommend this tour for first time visitors to Martha’s Vineyard.

11. Polly Hill Arboretum

Located in picture-perfect West Tisbury, this horticultural and botanical landmark features trees and shrubs from around the world set among stone walls, meadows, and fields. Developed by legendary horticulturist Polly Hill (1907-2007) the arboretum displays trees, scrubs and flowers, such as Polly’s famous North Tisbury azaleas, the national stewartia collection, camellias, hollies, rhododendrons, crabapples, conifers, and magnolias.

And, there is so much more on the island to explore! Ask us about:

  • Horseback riding
  • Moped/Jeep Rentals
  • Golf Courses
  • Up Island

12. Martha's Vineyard Theater Foundation

Let's go to the movies! Take a cinematic trip back in time with a visit to The Strand in Oak Bluffs and The Capawock in Vineyard Haven, operated by the Martha's Vineyard Theater Foundation. Built in the early 20th century as "places for amusement," both single screen theaters have undergone extensive renovations while retaining their historical island charm. The theaters are seasonal (mid-May to mid-October) and offer nightly showings of blockbusters, classics-in-the-making, engaging documentaries, and local film festival presentations.

For Vineyard events, virtual tours, live web cams and blogs, be sure to consult the Martha’s Vineyard Online or the Chamber of Commerce websites. For ideas on the perfect Martha’s Vineyard weekend getaway, consider this New York Times advice from Danielle Pergament’s 36 Hours on Martha’s Vineyard.