"For a little bit of nightlife, head to the Ritz, a lively dive bar in Oak Bluffs. They host live music and DJs most nights while slinging cocktails and beers from behind the bar. Order bar food classics like wings, burgers, and pretzels. On Sundays, Pocket Dogs pops up with $6.50 gourmet hot dogs from 1 to 6 p.m." - Celina Colby