The island classics
- See the Aquinnah Cliffs and the Gay Head Lighthouse, then stay for the sunset. Aquinnah guide.
- Ride the Flying Horses in Oak Bluffs and walk the gingerbread cottages of the Camp Ground. Oak Bluffs guide.
- Watch the sun go down in Menemsha with fish and chips from the harbor. Chilmark guide.
- Walk Edgartown’s harbor to the lighthouse, then take the Chappy Ferry across. Edgartown guide.
- Bike from Oak Bluffs to Edgartown along State Beach. Bike paths.
- Saturday morning at the West Tisbury Farmers Market. West Tisbury guide.
Places worth the trip
The red brick lighthouse sits above the colorful clay cliffs; climb it in season and walk the overlook at sunset.
Website →Wampanoag history and culture museum in the historic Vanderhoop Homestead near the cliffs.
Website →Harbor lighthouse at the end of a short walk from North Water Street, cared for by the Martha's Vineyard Museum.
Website →Built in 1876, it is America's oldest platform carousel and still gives rides with the brass ring in season.
Website →The Campground's gingerbread cottages surround the open-air iron Tabernacle; grounds are free to walk and there is a small cottage museum.
Website →Island history museum in the restored 1895 Marine Hospital overlooking Lagoon Pond.
Website →Seventy-plus acres of gardens, meadows and rare trees, with grounds open daily from sunrise to sunset.
Website →Quiet Japanese-style garden on a pond, cared for by The Trustees.
Website →The short crossing between Edgartown and Chappaquiddick for walkers, bikes and cars.
Website →Mass Audubon sanctuary with about four miles of easy trails through woods, meadows and salt marsh.
Website →Sheriff's Meadow Foundation preserve with trails through forest and bog down to a Vineyard Sound beach.
Website →Trustees refuge with a south shore beach, ponds for paddling and walking trails.
Website →Barrier beach of about seven miles with the Cape Poge Lighthouse, reached on foot or by permitted over-sand vehicle.
Website →Trustees beach at the southeast corner of Chappy, popular for surf fishing; swimming can be hazardous due to currents.
Website →The Land Bank owns many beaches and trail properties across the island that are open to the public.
Website →Over 5,000 acres in the middle of the island with paved bike paths, trails and a disc golf course.
Website →Arts campus with galleries, classes and summer events on six acres off Barnes Road.
Website →The island's year-round professional theater, in a restored 1833 church on Church Street.
Website →Home of the Martha's Vineyard Film Society, screening independent, classic and world films year-round.
Website →Nine-hole course from 1936 in West Chop that welcomes visiting golfers when tee times allow.
Semi-private club with an 18-hole course and tennis that takes public tee times, easier to get in spring and fall.
Website →Day and sunset sails from Vineyard Haven aboard the schooner Alabama.
Website →Private sailing charters from Vineyard Haven aboard a 42-foot sailboat, May through October.
Website →Inshore and offshore fishing trips from Menemsha with Capt. Buddy Vanderhoop, a member of the Wampanoag Tribe of Aquinnah.
Website →Water sports shop on Beach Road renting kayaks, paddleboards and sailboats, with lessons and delivery.
Website →Kayak and paddleboard rentals on State Beach and guided paddling tours.
Website →Bike rental shop near the Vineyard Haven ferry that also delivers island-wide.
Website →Upper Main Street bike shop for rentals, e-bikes, sales and repairs.
Website →Rainy day ideas
- The Martha’s Vineyard Museum in Vineyard Haven.
- A movie at the Martha’s Vineyard Film Center or a matinee at the Playhouse.
- Bookstores and galleries along Main Street in Vineyard Haven and in Edgartown.
- A long lunch and a game night: the best rental homes come with a shelf of board games.
Updated October 2026. Hours, seasons and rules change: check with each business or town before you go.