The Vineyard has three distinct seasons, at least when it comes to travel. From Memorial Day to Labor Day, beach weather is perfect, prices at hotels and inns run high, and ice cream shops have lines out the door. Forget what you know about typical East Coast weather—everything is tempered on the island, making for cooler summers and warmer winters than what you get in Boston. Of course, this being an island, things can turn stormy, rainy, and foggy no matter the time of year. By July, the water warms up to a comfortable temperature for swimming and stays that way until October. High season is the time to come for most events, whether it’s the Striped Bass and Bluefish Derby (September); the 5K Chilmark Road Race (August); Grace Church lobster rolls (Friday afternoons in Vineyard Haven); theater at the Vineyard Playhouse; or the relatively new and eclectic Aquinnah Music Festival, which brings together hip-hop, bluegrass, and folk in a natural amphitheater on the Gay Head Cliffs (July). Expect multiple summer solstice celebrations and opportunities for parades and fireworks.
In spring and fall—the shoulder season—rates drop, but the weather is still mild and the pace of life relaxes. September and October are prime months for destination weddings. After October, the island empties and only locals remain behind.
If you don’t need the beach and want good deals on lodging, come in the winter: Though some businesses are closed, there are plenty of boutiques and restaurants to keep you entertained. And the holidays are magical (think snow-covered sand dunes and gingerbread Victorians strung with lights).