The town of Edgartown has the oldest architecture on the island, including many examples of Federal-style homes built by whaling captains in the 18th century, complete with white clapboard facades and widow’s walks. While the Vineyard never achieved the same prominence in whaling as New Bedford or Nantucket, you can learn more about the history at the Martha’s Vineyard Historical Society (59 School St., Edgartown, 508/627-4441, www.marthasvineyardhistory.org, 10 a.m.–5 p.m. Mon.–Sat. mid-June–mid-Oct.; 10 a.m.–4 p.m. Mon.–Sat. mid-Oct.–mid-June, $6–7 adults, $4 children 6–15, free children under 6), a complex of buildings filled with more than enough old artifacts to while away a rainy day.

Exhibits include scrimshaw whale’s teeth, Wampanoag arrowheads, models of whaling ships, and diaries of early settlers. The centerpiece of the compound, literally, is the huge Fresnel prismatic lens that used to shine from atop the Gay Head lighthouse.

The town of Vineyard Haven has its own collection of old captain’s houses, though not as impressive as those in Edgartown. It is also known as the main center for the island’s artists community, with galleries sprinkled throughout town. Near the ferry landing is the Black Dog Bakery (11 Water St., Vineyard Haven, 508/693-4786, www.theblackdog.com, $7), which has grown from a small sandwich shop supplying hungry vacationers boarding the ferry to a veritable symbol of the island. A complex of buildings now sells T-shirts, hats, beach bags, tennis balls, and every other imaginable object emblazoned with the eatery’s trademark black Labrador. The symbol has long since gone from cachet to cliché, especially after Bill Clinton gave a Black Dog cap to intern-turned-mistress Monica Lewinksy.