The Cardboard Box

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.

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

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

Nestled in a vibrant, historic building in Oak Bluffs, the Summercamp Hotel captures the charm of summer camp with chic rooms, harbor views, and a playful café.

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.

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

Nestled in a charming clapboard house, this cozy B&B offers warm hospitality, stylish rooms, and a prime location just steps from the beach and shops.

Nestled between bustling Oak Bluffs and Edgartown, this relaxed resort boasts cozy studios with kitchens, a refreshing outdoor pool, and easy beach access.

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.