Vineyard Haven is the town least buffeted by the dramatic population cycles of the summer and winter seasons. It’s a densely settled community, with a population that matches Edgartown’s but on one-quarter the land area.

One of the natural treasures of Vineyard Haven is its harbor, which is protected by two promontories of land known as East Chop and West Chop. “Chop” is an old word for jaws, and these two jutting landforms have left Vineyard Haven with a natural enclosure that made it one of the busiest harbors on the East Coast during the heydays of coastal schooners in the United States. Along that harbor are such working businesses as the Island’s main ferry terminal, the Island’s only gasoline and heating oil depot and the famous Gannon & Benjamin boatyard, one of the finest builders of classic wooden yachts in the United States.

The man-made treasures of Vineyard Haven speak mainly to the town’s history. A drive out to the West Chop point will take you to the lighthouse, and past impressive private homes with sweeping ocean views. A walking tour of downtown is a chance to enjoy such Island landmarks as the Bunch of Grapes bookstore, honored as the best private bookstore in the United States, the Black Dog Tavern and the Black Dog Bakery and bustling family businesses like the Net Result Fish Market.