Flying Horses Carousel

At night, this unassuming bakery transforms into an enchanting speakeasy, serving warm, massive apple fritters and a mouthwatering array of donuts from its purple back door.

Nestled by the water, Lookout Tavern serves up fresh New England seafood and burgers with creative cocktails, all while boasting stunning ocean views.

This funky spot serves up massive portions of Caribbean classics like ribs and oxtail amidst lively music and a nostalgic vibe, perfect for takeout.

Nestled in Oak Bluffs, this welcoming, sandy beach features clear waters, vibrant morning meet-ups, and stunning sunrises, perfect for all visitors.

Upscale spot in a tranquil space with seasonal, area-sourced New American fare & an ample wine list.

At Red Cat Kitchen, you’ll find a cozy, art-filled space serving up creative, ever-changing New American dishes with a local twist, all just a hop from the ferry.

Tony's Market in Oak Bluffs is a charming spot where you can munch on gourmet sandwiches, sip local beers, and stock up on fresh produce—all while basking in top-notch service.

Chow down on seafood classics and sip vibrant frozen cocktails while soaking up the harbor views, whether you’re on the breezy deck or inside.

Charming, cash-only eatery dishing out hearty Italian classics and New York-style pizza, perfect for a laid-back meal near the Oak Bluffs ferry.

This stunning 2-mile stretch of pristine sandy beach, known for its calm waters and kid-friendly vibe, was featured in "Jaws" and is perfect for family outings.