Martha's Vineyard Nightlife
Compared to the hangouts of Oak Bluffs, the watering holes of Edgartown are more upscale and attract an older crowd. After dinner at David Ryan's, a pedestrian-looking restaurant, the capri-pants-and-Top-Siders set gets loud and lively on frozen daiquiris (11 North Water St.; 508-627-4100; www.davidryans.com). Tanned couples gather at Détente's soapstone bar to sample from the impressive wine list (Nevin Square; 508-627-8810; www.detentewinebar.com). Henry's at the Harbor View Hotel (131 North Water St.; 508-627-7000; harbor-view.com/dining_henrys.asp) and Newes from America (23 Kelley St.; 508-627-7900; kelley-house.com/dining_news_from_america.asp) are staid alternatives for quiet conversation (both close at 11; the kitchens close at 10). Flip-flops and bathing suits are acceptable attire at Sea Shanty, a kitschy bar where stiff-upper-lip types from the neighboring Edgartown Yacht Club move early in the evenings and loosen up in time to party with the younger, rowdier crowd that shows up around 11 pm. Its fun harbor-view deck is the best feature, but there's also a personable bar staff, live music, and free-flowing beer and booze (31 Dock St.; 508-627-8622).
Oak Bluffs, particularly Circuit Avenue, is party central for the young and unrulywhere college kids come to let off steam from their summer jobs driving taxis and waiting tables. Hordes of them congregate at Island House, a rollicking sports bar (11 Circuit Ave.; 508-693-4516), and Sharky's Cantina, a tiny Spanish and Mexican eatery where the tequila flows freelyalthough it's the larger and newer Sharky's location on Upper Main Street in Edgartown that's the most hopping place on the island (31 Circuit Ave.; 508-693-7501; www.sharkyscantina.com). Things can get pretty sweaty on the dance floor of The Lampost, where the live music includes reggae and rock bands (111 Circuit Ave.; 508-696-9352). When it's time to cool off, head for the string of outdoor bars and fried-fish restaurants (just a short stagger away) along the harborside wooden boardwalk known as Dockside Marina. However, the best bar on the Vineyard isn't on the Oak Bluff's harbor or main drag; it's the Offshore Ale House, a microbrewery one block over from Circuit Avenue, with excellent food, spirited conversation, live music, and great beer made in those big vats just above your head. Distinguished by the carpet of discarded peanut shells on the floor (it's known around town as the "peanut bar"), the Offshore Ale House also has an open kitchen that turns out sophisticated takes on pub food and wood-fired, brick-oven, thin-crust pizzatry the truffled variation (Kennebec Ave.; 508-693-2626; www.offshoreale.com).