Martha’s Vineyard by Bike

Get recommended bike trails and rentals for two-wheeled touring of the island.

One of the best ways to tour Martha’s Vineyard is by bicycle. There are many options depending on how much time you have (and how fit you are!). Bring your own bike over on a ferry or rent one at any number of spots close to the docks to explore the island on your Martha’s Vineyard vacation.

There are bike paths recommended by Martha’s Vineyard Chamber of Commerce, which I have condensed below. Visit its Web site for other ideas. And remember, if you end up biting off more than you can chew, you can always flag down a Vineyard bus, which are equipped with bike racks. Make sure you have the dollar fare though!

Down-Island Route

The “down-island” Martha’s Vineyard trail, from Vineyard Haven to Oak Bluffs to Edgartown and back, is about 25 miles round trip. It is mostly flat and an easy ride. You can tackle all of it, or just parts.

To West Chop Lighthouse

From the Steamship Authority dock in Vineyard Haven, proceed straight up Union Street one block to Main Street, turn right on Main and proceed out of the central shopping district. Bike up Main Street out to West Chop (two miles) to see the West Chop Lighthouse and the summer homes. The road makes a lazy loop just past the lighthouse and returns you to Vineyard Haven center.

Vineyard Haven Harbor

Take Beach Road from Vineyard Haven to Oak Bluffs (3.3 miles). When you get into Oak Bluffs, just past Sunset Lake on your right (at the foot of a hill on New York Avenue leading into town), turn right onto Dukes County Avenue and then bear to the left to enter the Methodist Campgrounds. Ride around the circle of cottages to see the wrought-iron Tabernacle.

Exit by the Wesley Hotel, turn right and park your bike near the Flying Horses Carousel, the nation’s oldest continuously operating carousel. This area is the heart of Oak Bluffs. If you continue past the Flying Horses Carousel straight towards the ocean, you come to Seaview Avenue, which runs along the water past Ocean Park.

Oak Bluffs to Edgartown

Biking on Seaview Avenue from Oak Bluffs to Edgartown (six miles), you come to a paved, off-road bike path along the Joseph Sylvia State Beach. The fantastic view from this path makes it a popular route. Follow Beach Road to Upper Main Street in Edgartown, just beyond the Edgartown Triangle. Before you enter Main Street, traffic signs will direct you down Pease’s Point Way on your left. You can park your bike here for a walk through Edgartown.


A short ferry ride on the On-Time Ferry (leaving from the Edgartown town dock) takes you to Chappaquiddick, where you can bike to Wasque Beach two miles away. You can also visit the Mytoi preserve, a beautiful Japanese garden.

Up-Island Trek

Heading to Chilmark and Aquinnah is a tougher route, with hilly terrain and curvy roads. Plus, there are no bike paths or streetlights for the major part. This is not really a place for a family bike ride. One option is to bus up and bike back or to use West Tisbury as your starting point.

To Menemsh

From Edgartown, take the West Tisbury Road to West Tisbury center (four miles), marked by Alley’s General Store, the Field Gallery and the Grange Hall. Continue on South Road to Beetlebung Corner (5.4 miles), the center of Chilmark. Turn right and ride on to Menemsha (1.5 miles), the island’s small fishing village.

To Aquinnah

In Menemsha, you can rest and still get to Aquinnah with the bike water shuttle that operates in the summer. The Aquinnah Cliffs, a National Historic Landmark, should be a required stop. They were formed 10,000 years ago and feature magnificent colors.

To Vineyard Haven

Take State Road from Aquinnah to Beetlebung Corner (6.5 miles). For gorgeous views, continue straight at Beetlebung Corner and take Middle Road to Music Street in West Tisbury (5.4 miles). Turn left from Music Street to State Road. Continue on State Road toward Vineyard Haven (nine miles).  

Customized Cape Cod Tour 

For those who prefer to not bike it alone, here’s a bike tour option.

Roger and Suzie Knable started the Maryland-based Bike and the Like touring company in 1994 to promote cycling and human-powered travel. The couple personally host each trip and handpick accommodations and activities for guests. Their seven-day Cape Cod, Martha’s Vineyard & Nantucket trip was voted one of the best cycling tours by Bicycling Magazine. The two-day Martha’s Vineyard portion of the trip offers lodging at Madison Inn and breakfast at Linda Jean’s Restaurant in Oak Bluffs. [Read more about Linda Jean’s in Best Martha’s Vineyard Dining.]

Tel. 410-960-6572 or 877-776-6572. Package starts at $985 per person. Dates for Cape Cod tours: Sept. 11 to 18 and Sept. 19 to 26, 2009.

Destinations: Martha’s Vineyard

Themes: Beach Vacations

Activities: Cycling, Sightseeing