See and be seen at the upscale American bistro Alchemy (71 Main St., Edgartown; 508-627-9999), whose large windows offer curious passersby a glimpse inside the stylish dining room. Sip a cocktail at the downstairs bar (try the New Orleans–inspired, Peychaud’s bitters-infused French Quarter, $13) before heading up to a booth on the quieter second floor for seasonal fare like butternut squash ravioli ($16), and year-round favorites like the tangy Jonah crab salad ($17).
Join islanders who like to warm up by the fire at Newes From America Pub, housed inside one of the Vineyard’s oldest buildings (the 1742-constructed Kelley House), and whose walls still contain ballasts from the original settlers’ ships. Straightforward pub fare like fish and chips ($14) and bangers and mash ($15) is best enjoyed accompanied by a five-glass sampler rack ($13.50) of the pub’s mostly New England ales.
Give the Black Dog a rest and head to the somewhat quirkier Art Cliff Diner (39 Beach Rd., Vineyard Haven; 508-693-1224), Vineyard Haven’s version of the traditional roadside diner, complete with retro signs on the walls and frequent coffee refills. The vibe is laid-back but lunch hour can get a little jammed, so your best bet is to show up around 11 a.m. for a leisurely brunch of black bean crepes ($8), blueberry pancakes ($9), or crab cake eggs Benedict ($10.50).