Soft As A Grape — Oak Bluffs

You'll spot the Soft As A Grape shop right on Circuit Avenue, perfectly placed for shoppers working their way through Oak Bluffs' lively main drag. This is the island's most casual-cool clothing stop — 100% cotton tees, comfortable sweats, and nautically inspired apparel that captures the spirit of a Martha's Vineyard summer without any fuss. Originally founded as a wine-making supply shop in 1972, the brand evolved into a staple of New England coastal retail with locations across the island and beyond. The Oak Bluffs shop is open daily with extended hours, and you can drop in after dinner or between activities. Pick up a matching set for the family, grab a classic Vineyard graphic tee, or find the perfect soft sweatshirt to make the ferry ride home a little cozier.