Every year come September, the majority of Martha’s Vineyard closes up shop. This may leave most to assume that there’s no good reason to head there after the summer, yet many a Vineyard regular will tell you that the 87-square-mile island is in fact quite an off season paradise. You may not find yourself soaking up the sun at Lucy Vincent Beach or queuing up for a double scoop at Bernie’s Ice Cream; but the Vineyard’s magic is by no means limited to the summer months.
One of the best things about visiting Matha’s Vineyard in the shoulder seasons is how easy it is to take your car out via the Woods Hole Steamship Authority ferry. Reservations are required well in advance for the summer months; however, in the fall, you can take your car out on a whim and enjoy exploring the island on four wheels to see all the best foliage, especially up island in Chilmark and near the Gayhead Lighthouse in Aquinnah.
While September may mark the end of the summer season, it brings with it the prestigious International Film Festival, which falls around the first week of the month. Shortly after, in October, island-goers can enjoy the annual Food & Wine Festival, a lively celebration of the Vineyard’s local farms, fisheries, and culinary talent.
You’ll find the Vineyard is just as striking in the colder months, when strong winds whip across the dunes and offer an excellent excuse to hunker down. Cozy into a room in Edgartown’s recently renovated Harborview Hotel, where you can stay in upscale accommodations and dine on fresh seafood right on the property at Bettini (prepare yourself for some breathtaking views from the dining room). If you want a particularly intimate experience, book the Presidential Skyhouse, which offers a stunning oceanside vista, a private butler service, and four spacious bedrooms. (The Harborview Hotel’s winter schedule is as follows: open Thursdays to Sundays November 1, 2019 to April 1, 2020; closed for maintenance January 5 to February 5, 2020).
Spend your days basking in springtime sun on uncrowded beaches and hiking on the island’s many sandy trails (Felix Neck is a great place to start). With 44 miles of bike paths, there’s plenty of off-road exploring to be done, and the spring months (and mild weather) yield beautiful views of the sparkling Sound. Celebrate the newly warm temperatures with a seafood dinner at Alchemy, or sit for a dozen cold water oysters at 19 Raw Oyster Bar in Edgartown (open April to November). Mid-April brings not only the first bout of colorful flowers, but also the 19th-century Flying Carousel in Oak Bluffs. Open for rides beginning April 13, the carousel is the oldest in the nation, and a beloved local landmark—especially for little ones.