History of Martha’s Vineyard

Encompassing just 100 square miles, Martha’s Vineyard has six classic Cape Cod towns surrounded by farms, forests, beaches, and harbors. On the east side, or “down-island,” are the historic port communities of Edgartown, Oak Bluffs, and Vineyard Haven. On the west side, locally referred to as “up-Island,” are the rural villages of Aquinnah, Chilmark, and West Tisbury. Each town has a distinct atmosphere and its own intriguing history. The up-island towns of Aquinnah, Chilmark, and West Tisbury are quaint farming and fishing communities with several nature preserves, pastoral pastures, and vast stretches of beach.

Aquinnah is best known for the red clay Gay Head Cliffs and the historic red brick Gay Head Lighthouse and the island’s home of the Wampanoag Tribe.

Below the cliffs, Moshup Beach has strong surf, brilliant aqua blue water, and fantastic views of the sunset.

Above the cliffs, the Outermost Inn serves spectacular food. It offers stunning views of the countryside from its deck and lawn seating, where you can relax and take in the view.

Chilmark is just east of Aquinnah, with its rolling hills and dramatic coastlines. Chilmark includes Menemsha, a fishing village with quaint shops and fresh seafood, Menemsha Beach with its famous sunset views, and Prospect Hill, the highest point on Martha’s Vineyard.

Next over is West Tisbury, characterized by its rural charm and historic downtown. Features the oldest continuously operating business on the island, Alley’s General Store, and the Field Gallery, with its collection of unusual and playful lawn sculptures.

Nearby Long Point Wildlife Refuge offers an abundant bird population, hiking trails, and a large freshwater pond separated from the ocean beach only by a row of dunes.

Down-island, to the east, you’ll find the busier harbor towns of Vineyard Haven, Oak Bluffs, and Edgartown. Vineyard Haven, also known as Tisbury, has the island’s main ferry landing, scenic harbor views, and a bustling Main Street for shopping, dining, and people watching.

The town is best known for its unique boutiques, numerous art galleries, the Martha’s Vineyard Film Center, and the Vineyard Playhouse.

Further to the east, Oak Bluffs also has ferry service in season and a vibrant downtown experience with an active music and arts scene. Main attractions include the historic Flying Horses Carousel, the colorful cottages of the Methodist Campground, and Inkwell Beach. Its warm, shallow waters, swim clubs, yoga classes, windsurfing, kayaking, and jet skiing.

Finally, Edgartown sits south of Vineyard Haven and Oak Bluffs and features several iconic captain’s houses, beautiful churches, lighthouses, and miles of beaches. Just outside of town, several conservation areas offer hiking trails and wildlife viewing opportunities. Included are the Cape Poge Wildlife Refuge, Woodland Wonderland, and Felix Neck Wildlife Sanctuary.

With their close proximity to the small island, you could certainly visit all of Martha’s Vineyard’s towns in a day, but you would miss so much. Your best bet is to take a day for each and explore all the history, nature, shopping, dining, and entertainment the town has to offer before moving on to the next.