Up Island:

Aquinnah (formerly Gay Head) is located at the western tip of Martha’s Vineyard.  The mile-long, red and orange clay cliffs in Aquinnah are a national landmark.  Aquinnah is one of the more rural communities on the island.  Most of it’s year round residents are decendants of the Wampanoag Indian tribe. 

Chilmark is bordered by Vineyard Sound to the north and the Atlantic Ocean to the south.  It’s rolling hills, once predominantly farmland, are now the site of many beautiful summer homes.  Menemsha harbor has many private boats, a fishing fleet, and a Coast Guard station

West Tisbury is a classic New England village with its white church, town hall, general store and scattered farms.  There are several nature preserves in West Tisbury, including Cedar Tree Neck and the Polly Hill Arboretum.

Down Island:

Vineyard Haven is located at the northern tip of Martha’s Vineyard.  Its protected harbor and convenient location made it one of the busiest New England ports during the 1800s.  Its harbor is now home of many private and commercial boats and is primary year-round ferry terminal for car ferries from Wood’s Hole.  Vineyard Haven sports many great shops and restaurants.

Oak Bluffs was the summer campground for the Methodist Church during the 1800s.  The campground eventually evolved into a community of brightly painted gingerbread cottages.  Oak Bluffs is home of the Flying Horses, the oldest carousel in America.  Oak Bluffs’ harbor hosts a large number of private and commercial sport fishing boats as well as two ferry terminals.  There are a number of waterfront restaurants and bars.

Edgartown is located in the southeast corner of Martha’s Vineyard.  Edgartown is an upscale community boasting many fine shops and restaurants.  With its large, protected, deep water harbor, Edgartown is a popular cruising destination and home of many fine sailboats and power boats.  There are typically several 100+ foot yachts in the harbor at any given time during the summer.