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The Five-Point Weekend Escape Plan

Taste Fall Flavors on Martha’s Vineyard

2. Where to Eat

It's worth the drive to State Road, where the island's autumn harvest takes center stage.  

Arrive early to claim a spot among the popped-collared and whale-belted crowd at the Port Hunter in Edgartown. Communal tables fill up as reggae or blues bands entertain the crowd nightly. Keep an eye on the market specials: Chef Jeremy Davis has made a commitment to using less common local catches, like bluefish and ocean perch, and puts one whole fish and one fillet on the menu each night. Or tuck into the slow-roasted chicken ($29), fresh-shucked raw bar, and an eclectic craft-beer list with local brews like Offshore Ale. Cap off your meal with the pavlova ($12); the Aussie favorite comes with fresh berries and cream.

Grab a glass at 20byNine, the island’s first craft-beer and whiskey bar, which just opened this year in Oak Bluffs. The name is drawn from the dimensions of the island, and the menu is, as well, with small plates like gnocchi and littleneck clams ($11) and Katama Bay oysters ($12), and entrées like a pair of young chickens served Peking style with fresh kale and duck-fat-fried potatoes ($40 for two). Chef Scott Cummings’s dishes all come with suggested drink pairings—the 16 draft beers, up to 30 bottles, and over 60 whiskeys are all American-made—but the sole dessert is a perfect complement unto itself: an ice-cream float made with caramel, whiskey-soaked pineapple, and crushed housemade beer nuts, served with Bell's Java Stout.

Venture “up island” to the Vineyard’s less-populated western side to sample seasonal New American cuisine at local stalwart State Road. The agrarian outpost’s remote location hasn’t stopped diners like the Obamas and Seth Meyers’s wedding after-partiers from trekking out to its refined barnlike space (the century-old beams are sourced from the original Necco candy factory in Cambridge). Stroll the elaborate edible gardens, then pull up a seat at the gorgeous zinc bar for a pour from their extensive domestic wine list or even their mean “Coast” mocktail, a blend of grapefruit, club soda, lime, and salt (the place opened first as BYOB, thanks to the town of West Tisbury’s longstanding dry status). Married owners Jackson and Mary Kenworth chose the restaurant’s location thanks to its proximity to nearby farms, whose produce stars in inventive, fresh dishes like pancetta-wrapped bluefish ($34), duck-confit panzanella ($19), and a chocolate-raspberry Black Forest torte paired with mint gelato ($12).

Published on Sep 25, 2014 as a web exclusive.