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Drive through all the unique towns and recognizable landmarks which make the island what it is today on a self guided tour.

AQUINNAH, located at the westernmost tip of Martha’s Vineyard (known as Up-Island), is a small town covering less than six square miles of land with a population of just over 2,100 people. It is best known for the brightly colored clay cliffs, known as the Gay Head Cliffs, and the historic Gay Head Lighthouse. The town is also home to the Wampanoag Tribe of Gay Head (Aquinnah), a federally recognized Native American tribe.


  • Gay Head Lighthouse
  • Gay Head Cliffs
  • Moshup Beach
  • Wampanoag Tribe of Gay Head (Aquinnah) shop – Islander’s Tip: Take home beautiful one of a kind Wampum jewelry, photography, and gifts.

CHILMARK, located Up-Island next to Aquinnah, is famous for its scenic rolling hills, stone walls, nature preserves, and breathtaking coastlines. If you take South Road, you can catch a glimpse of Noman’s Land, a federal bird sanctuary that’s closed to human visitors. On the north shore, you’ll be able to enjoy stunning views of the Elizabeth Islands chain. Menemsha, a charming fishing village, is also part of Chilmark and is known for its delicious and fresh seafood. You can also witness the best sunset views on the Vineyard from Menemsha.


  • Chilmark General Store
  • Great Rock Bight Preserve
  • Catch a sunset
  • Grey Barn
  • Lucy Vincent Beach
  • Menemsha – Islander’s Tip: The locations of the fictional town of “Amity Island” in the 1975 Steven Spielberg movie Jaws.

EDGARTOWN, originally established as Great Harbour, is located in the southeastern corner of Martha’s Vineyard. It holds the distinction of being the oldest English settlement on the island. The town’s architecture is renowned for its white-painted captain’s houses and grand churches, which date back to the prosperous era of whaling. The plains district near the expansive South Beach is known as Katama (Kah-TAY-mah). In addition to its historical significance, Edgartown is also home to the Vineyard Gazette and the Felix Neck Wildlife Sanctuary.


  • Carnegie, Vineyard Preservation Trust
  • Chappaquiddick/Mytoi Gardens
  • Edgartown Books
  • Eisenhauer Gallery
  • Edgartown Lighthouse/Beach
  • Felix Neck Wildlife Sanctuary
  • Morning Glory Farm
  • Murdick’s Fudge
  • North Water Gallery
  • Old Sculpin Gallery
  • Old Whaling Church
  • South Beach/Katama
  • The Farm Institute
  • Vineyard Gazette Office
  • Vineyard Vines – Insider’s Tip: The flag ship store. You can only buy apparel with the Martha’s Vineyard map on island. 

OAK BLUFFS: North of Edgartown, Oak Bluffs is home to two main ferry ports on Martha’s Vineyard. It blossomed as a center for summer religious retreats, with its open-air Tabernacle built in 1879 located in its central park amidst colorful gingerbread cottages. One of Oak Bluff’s best features is the miles of public beaches available to visitors.


  • Barn & Bowl Bistro
  • Circuit Avenue
  • East Chop Lighthouse
  • Flying Horses Carousel
  • Gingerbread Houses
  • Inkwell Beach
  • Joseph Sylvia State Beach a/k/a Bend-in-the-Road Beach (Jaws Bridge)
  • Trinity Park Tabernacle
  • The Game Room
  • The Lazy Frog

VINEYARD HAVEN: This town has two names that are almost interchangeable. The official name is Tisbury, which is used by the town government and school. However, the Vineyard Haven Post Office and Public Library refer to it as Homes Hole. Homes Hole is a popular fishing village on the East Coast and is still the main port of entry, open year-round.


  • Black Dog Bakery (founded 1971)
  • Manuel  F. Cornelius State Forest
  • MV Museum
  • West Chop Lighthouse
  • Owen Park
  • Tisbury Town Beach

WEST TISBURY, located southwest of Vineyard Haven, has managed to preserve its rural charm despite the passage of time. The small downtown area houses Alley’s General Store which also serves as the town’s post office. Opposite the store, you can spot whimsical dancing lawn sculptures. This town is also known for its historical Grange Hall and the MV Agricultural Society, which hosts the famous fair every August. Additionally, the Polly Hill Arboretum is also located in West Tisbury.


  • Alley’s General Store
  • Cedar Tree Neck
  • Field Gallary
  • Granary Gallery
  • Lambert’s Cove Beach
  • MV Glassworks
  • Polly Hill Arboretum
  • Long Point Wildlife Refuge

A trip to the beautiful Island of Martha's Vineyard is only a few clicks away.