The Vineyard has activities year-round, whether you’d like to enjoy nature and take a beautiful walk, participate in community events, rent athletic equipment to explore… Below are just some of our favorites.

We always advise booking ahead when possible, and for the high season July-August, make any reservations you can well in advance. When visiting parks and beaches, and where admission charges apply, it’s wise to have cash on hand.

  • Celebrating its 25th anniversary as of 2023, the Heritage Trail follows thirty sites around the island, all marked by plaques detailing the contributions of people of color.

  • Visit the area at the top of the cliffs to learn more about the importance and history of the Wampanoag people on the island.

  • This protected area of Christiantown has a chapel and Wampanoag burial grounds.

  • The Martha's Vineyard Camp Meeting Association manages the grounds and activities for the gingerbread cottages in the center of Oak Bluffs. This community began as a summer campground for Methodists visiting the island for community gathering and prayer. Stroll the area to take in the elaborate architecture and vibrant colors of this unique location. There are summer concerts on Friday nights 6:00-7:30 (free, donations encouraged).

  • If you’re lucky to be on the island for Illumination Night, don’t miss it! Grand Illumination is the 3rd Wednesday in August, and all the cottages in the Oak Bluffs campground are illuminated with lanterns – it’s magical.

  • Commonly referred to as the, “MV Museum,” this place was once the island’s naval hospital, and now houses temporary and permanent collections about the natural, political, and creative histories of the island.

Island history

  • Ryan Amusements on Circuit Avenue is a couple levels of classic, colorful, loud arcade mayhem.

  • Classic Aviators offer two-person biplane rides around the island, complete with goggles and an audio tour from the captain.

  • The Barn & Bowl Bistro has great drinks, bar snacks and full meals, and bowling.

  • In July and August, Community Sings take place in the Tabernacle at 8:00pm every Wednesday. Visitors of all ages can sing along with a large band – bring a picnic and some chairs to enjoy the lawn, or sit on the Tabernacle benches.

  • The Farm Institute offers tours of the working farm, which is also an educational space.

  • The Flying Horses is the nation’s oldest platform carousel, and is one of the oldest still in existence. If you get the brass ring, you’ll earn another turn. There’s also a small arcade onsite, and the carousel is at the base of Circuit Avenue in Oak Bluffs, perfectly located to take a spin around town.

  • Visit Island Alpaca year-round to see the animals, learn about farming their wool, and buy alpaca products.

  • Visit the farm to meet the goats, take art classes, and to learn more about the island and native plantings.

  • MV Pirates is based out of the Oak Bluffs harbor, and while it may technically be for kids, the ship can also be privately chartered for sunset cruises (we know from experience).

Family fun

  • The Gazette’s calendar has a thorough and frequently updated list of island events.

  • The Flea runs 9:00–2>00 on Wednesdays and Saturdays, mid-June through Labor Day, and is the oldest outdoor venue on the island, with hand made items, antiques, and vintage.

  • The historic Derby runs annually for a month from the second week in September.

  • First Friday is a free community-inspired outdoor event.

  • This farmers’ market runs all summer long, rain or shine.

  • The Wind Festival is a free event in Oak Bluffs’ Ocean Park includes kite making, model sailboat racing for children, and kite flying and frisbee games for all.

  • The Artisans Festivals run summer though the winter holiday season, and highlight some of the best arts and crafts of the island.

Markets & Annual Events

  • Island Spirit Kayak in Oak Bluffs offers canoe and kayak rental, as well as organized events, such as sunrise and sunset tours.

    Wind’s Up in Vineyard Haven rents boards, kayaks, sailboats, canoes, and windsurfers, and offers lessons.

  • Farm Neck is one of the most beautiful courses in the country, with sprawling ocean views. Tee times can be reserved three days in advance, and the course is open mid-April through Thanksgiving.

  • Felix Neck has wonderful walking paths and beaches to explore year-round. Mass Audubon members visit for free; non-members pay $4.00 per per (as of spring 2023).

  • Long Point in one of the largest publicly accessible properties on the entire island. From mid-September to mid-June, access is free. Mid-June to mid-September, there are a range of admission costs for bike and car access (children 15 and under are free).

  • A visit to Mytoi (pronounced “MY-toy”) combines two things: a ferry ride on the Chappy ferry and experiencing this beautiful Japanese garden.

  • Ocean Park is the beautiful area right by the OB ferry, complete with views of the ocean and the quintessential gingerbread homes (some of the very finest examples on the island. Picnic, play some soccer, swim… it’s so easy.

  • Take a stroll year-round through this beautiful sprawling arboretum, open sunrise to sunset.

  • It’s a kind of right of passage on the island to bring a picnic to Menemsha and watch the sunset. Parking is very limited, so plan ahead, or make a full day of it and enjoy the beach. We love grabbing fish sandwiches from Larsen’s, and then ice cream from Marshall’s Texaco.

Outdoor activies