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The Five-Point Weekend Escape Plan

Enjoy the Off-season in Martha’s Vineyard


5. Oddball Day

Gay Head is one of the island's most stunning lookout points.  

Soak up the Vineyard’s natural beauty on a leisurely up-island drive—minus the obnoxious summer crowds and traffic. Start off the day with a brunch of housemade, granola-encrusted French toast ($9) at Black Dog Tavern, the island’s best-known restaurant. After you’ve warmed up by the fireplace, drive fifteen minutes west to Great Rock Bight Preserve, where a short, one-mile hike through dense woods leads down to a dramatic 1,300-foot stretch of beach. Gaze west from here to catch a glimpse of the Aquinnah Cliffs, where a lighthouse was built in 1799 using bricks made from the cliffs’ natural clay. Afterwards, make a quick stop at Alley’s General Store (299 State Rd., West Tisbury; 508-693-0088)—the area’s main hardware store, post office, and convenience store, all rolled into one since 1858—and shop for gag items like a metal-and-rubber-band jaw harp ($2.99) and a cobra oil soap bar ($7.49). Once you’ve loaded up on souvenirs, have lunch at the vegetarian-friendly Scottish Bakehouse, and be sure to leave room for some of the bakery’s decadent flourless chocolate cake, gluten-free brownies, or Scottish shortbread. Next, drop by Allen Farm Sheep & Wool Co. (421 South Rd., Chilmark; 508-645-9064), whose unmanned shop, selling hand-knit sweaters, specialty foods and other gifts, works on the honor system during the off-season, allowing for a relaxed, unhurried shopping experience. Then drive along State Road, taking in the beauty of the surrounding windswept dunes, until you reach Gay Head, the alternate name for Aquinnah Cliffs. Stroll up the path, bypassing the mostly useless souvenir shops, until you reach the landmark’s stunning lookout point: from here, watch the sun set over the Atlantic. Finally, circle back to Vineyard Haven, where the newly opened Martha’s Vineyard Film Center ($10) screens a mix of international contemporary and classic films like Jules and Jim and the dance documentary First Position. Next door, keep dinner simple with a slice ($2.75) at local favorite Rocco’s Pizza (14 Beach Rd., Vineyard Haven; 508-693-1125).

Published on Oct 12, 2012 as a web exclusive.

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