Concierge.com's insider take:
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).
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