- First Friday - Friday, September 2 at 4:00pm to 11:00pm - First Friday is an outdoor event in Vineyard Haven, Martha's Vineyard.
- Vineyard Artisans Labor Day Weekend Festival - Friday, September 2 through Sunday, September 4th - The largest art show on Martha’s Vineyard featuring Island artists with unique furniture, clothing, ceramics, jewelry and fine art from the Islands top artists.
- Oak Bluffs Arts District Stroll - Saturday, September 3 at 4:00pm to 7:00pm - Dukes County Avenue Art District galleries will open their doors and invite the public for art, socializing and entertainment.
- The Vineyard's Drive-In: Friday, September 2 at 6:30pm, The Lego Movie. Saturday, September 3 at 6:30, Spider-Man No Way Home - The Vineyard's Drive-In at the YMCA is a pay-what-you-can event.
- Foot It for Felix 5K Trail Walk / Run - Saturday, September 3 at 9:00am - The race takes you through the beautiful trails of Felix Neck Wildlife Sanctuary, providing views and inspiration at every step.
- Sundays in the Park Concerts: The Black Eyed Susans - Sunday, September 4 at 5:30pm to 7:30pm - Made possible by the Oak Bluffs Parks Department.
- International Film Festival - Tuesday, September 6 through Sunday, September 11 - The recurring theme of the annual Martha’s Vineyard International Film Festival is “Other Places, Other People."
- Geraldine Brooks' Horse, To Benefit Vineyard Haven Library - Wednesday, September 7 at 5:00pm - Vineyard Haven Library Building Fund presents Pulitzer Prize-winner Geraldine Brooks in a discussion of her latest novel, Horse, based on the remarkable true story of the record-breaking thoroughbred Lexington.
- Moonrise Kayak Tour - Friday, September 9 at 5:30pm to 7:30pm - See Sengekontacket Pond in a new light—moonlight—as we celebrate each month's full moon.
- Martha's Vineyard Wind Festival - Saturday, September 10 at 6:15am to 4:30pm - Events include kite making and model sailboat racing for children, and kite flying and frisbee games for young and old.
- Martha's Vineyard Striped Bass & Bluefish Derby - Sunday, September 11 at 12:01am - For 77 years, "The Derby" has been a time to renew friendships, share a cup of coffee and create memories that fuel the winters exaggerated fishing stories.
- Poucha Pond Kayak or SUP Rentals - Sunday, September 11 at 9:00am to 3:00pm - Explore Poucha Pond and the salt marshes of Chappaquiddick by kayak.
- Salt Water Wednesdays - Wednesday, September 14 at 4:00pm to 5:00pm - Have you ever wanted to learn how to gut and fillet a fish? Sign up for this monthly workshop where you will learn about all aspects of Island seafood, from preparation to the ecological importance of buying local.
- Jon Stetson: America's Master Mentalist - Friday, September 16 at 7:30pm - Live Performance at the Film Center - One Night Only. There is simply NO other audience interactive performer like Jon Stetson.
- Tivoli Day Celebration - Saturday, September 17 at 8:00am to 7:30pm - An annual celebration of summer’s end on Circuit Avenue, featuring live music, arts, crafts, great food and family fun.
- Kids Derby Day - Sunday, September 18 at 6:00am to 8:00am - Part of the annual Martha's Vineyard Striped Bass & Bluefish Derby. For kids 4-14, no registration needed. Fish are judged not by weight, as in the main derby, but by length.