Brasserie–style Détente , in Edgartown, serves locally raised organic chicken and island-grown veggies in a golden-hued dining room dotted with black-and-white photos of European wineries. If you can’t snag a reservation (this has been one of the island’s most popular restaurants since opening in 2005), go before 7:30 and grab a spot at the seven-seat bar.
Owned by James Taylor’s brother Hugh and his wife Jeanne, the Outermost Inn unsurprisingly attracts a celebrity crowd: Bill Clinton, Carly Simon, Dan Aykroyd, and of course, brother James. But despite the high-profile clientele, the vibe remains low-key and casual, thanks to the meadowy surroundings, the views of the sound, and cooking that makes use of locally grown squash blossoms and arugula, herbs from the Taylors’ own garden, and just-caught striped bass.
Book at least a month ahead in the summer to secure a table at the perennially packed Beach Plum in the fishing village of Menemsha. Though the décor's a bit Pottery Barn, the ocean views and lenient BYOB policy are hard to knock. Bring a bottle of Chenin Blanc and pair it with the pan-seared halibut, served in a shallow bowl with tomato confit and basmati rice.
Island newcomer Mark Goldberg, formerly of Boston’s Mistral restaurant, mans the kitchen at Lure, the Winnetu resort’s nautically themed restaurant, which dishes out sublime Katama Bay oysters and butter-poached local lobster. Parents should request space in the family dining room, where there’s a kid-height buffet, beanbag chairs, and movies in the corner.