Tony's Market

This chic bakery turns into a speakeasy at night, serving giant apple fritters and fresh donuts from its purple back door.

Step into the charming Pequot Hotel, a cozy retreat just a block from the beach where rocking chairs sway on the porch and fresh cookies await daily.

Charming Victorian B&B in Oak Bluffs with comfy rooms, killer breakfasts, a sprawling porch, and top-notch hosts just steps from town and beach.

MV Salads in Oak Bluffs is a vibrant eatery where you can dive into unique, health-centric salads and wraps made with local ingredients, all served with a side of kindness.

Lookout Tavern serves up huge, buttery lobster rolls, fresh seafood, sushi, and cocktails with unbeatable waterfront views in lively Oak Bluffs.

Nestled in a quiet street, this charming bistro boasts innovative New American cuisine with fresh, local ingredients and a cozy garden patio perfect for any occasion.

The Cardboard Box offers a vibrant mix of refined New American dining with a seafood twist, plus excellent cocktails and a lively atmosphere perfect for summer nights.

Mad Martha's Ice Cream on Martha's Vineyard is a beloved summer hotspot, offering local, inventive flavors and a vibrant community vibe.

Casualwear and gifts decked out with the iconic dog logo for the whole family, blending island charm with everyday style.

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.