One of our regular evening locations while on the Vineyard was Oak Bluffs. The kids wanted to go for the ice cream (Ben and Bill’s is a favorite). I always like visiting Vineyard Vines (where I got these shorts last year on our first rip). I’ve linked two similar pairs below. There are several great restaurants including Slice of Life. The kids also love running around the green around the gazebo and riding the Flying Circus Carousel, which is the oldest operating platform carousel in the United States. You really can’t go wrong anywhere on the Vineyard, but evenings in Oak Bluffs are always fun. Shopping and ice cream? I’m in.
J. Crew Shirt (20% off with code LOTSTOSHOP)
Jimmy Choo Sandals (older style) similar here.