Edgartown, Massachusetts is a walking town on on Martha’s Vineyard with a compact village center, but the town itself is a total of 35 square miles. It contains miles of waterfront, either on the beaches, harbor or Edgartown Great Pond, with homes often tucked down dirt roads that feel especially “last century.” Edgartown also contains a portion of the Island’s state forest, with abundant walking, hiking and mountain bike riding paths.

The Town of Edgartown is an old whaling town that has reemerged as a charming village, characterized by elegant historic homes and churches. Main Street, Edgartown looks the way a Main Street in a small New England town should look: a one-way street barely two lanes wide with a few blocks of inns, shops and restaurants, a church or two and an old courthouse guarded by old growth elms.

The European settlement of Martha’s Vineyard began in Edgartown during the late 1600s. The town boasts a rich history as a whaling and shipping hub. Just off Main Street, there are modest houses dating from the 18th century, whalers’ mansions from the 19th century, and 21st-century renovations or reconstructions and additions scattered throughout.