Top Things to Do in Oak Bluffs

Flying Horses Carousel, Oak Bluffs, Alison Shaw
The Flying Horses Carousel in Oak Bluffs (oldest continuously operating carousel in the country) is a lively place to be on a rainy day. (photo by Alison Shaw).
  • Come in August to catch the annual fireworks and Illumination Night
  • Take a stroll up Circuit Ave for shopping, galleries, snacks, and more
  • Do a bar hop along the Harbor
  • Cast a line from the fishing pier while watching the ferries come and go
  • Rent a bike and cruise along the path to Edgartown
  • Ride the historic Flying Horses carousel
  • Toss some frisbees at the Riverhead Disc Golf Course
  • Take a paddle around Sengekontacket Pond
  • Hurl yourself off the famous Big Bridge