As the vibrant summer days give way to the crisp air of fall, Martha’s Vineyard comes alive with a variety of events that capture the island’s unique charm and spirit. This autumn, the Vineyard is packed with exciting festivals and celebrations that promise something for everyone. From arts and film to family fun and Halloween festivities, here are the top Martha’s Vineyard fall events you absolutely can’t miss this year!
Vineyard Artisans Festivals Fall Festival (October 12-13)
Kick off your fall season with the Vineyard Artisans Festivals Fall Festival, where you can immerse yourself in the extraordinary craftsmanship of local island artisans. This event showcases a diverse range of talents including weaving, fine furniture, pottery, leather goods, oil paintings, pastels, mixed media, sculpture, and stunning wampum jewelry. You’ll also find hand-knit items, unique clothing, photography, handmade books, and so much more.
6th Annual Women In Film Festival (October 18-20)
The Women In Film Festival (WIFF) is back for its sixth year, celebrating the voices and stories of women in the film industry. This three-day event is dedicated to showcasing films that feature strong female characters and highlight narratives often overlooked by mainstream cinema. With six diverse films, WIFF will take you on a journey through genres and stories that break the mold and challenge the status quo. It’s a fantastic opportunity to enjoy powerful storytelling and support women in front of and behind the camera.
Morning Glory Farm Pumpkin Festival (October 19)
Get ready for a day of wholesome family fun at the Morning Glory Farm Pumpkin Festival. This free celebration of the harvest is packed with activities that will delight kids and adults alike. From pumpkin carving and cider pressing to games, hayrides, and a mini-hay maze, there’s plenty to keep everyone entertained. Enjoy festive autumnal treats and delicious foods that capture the flavors of the season.
Halloween in Oak Bluffs
Halloween in Oak Bluffs is a spooktacular event that brings the community together for a fun-filled evening of trick-or-treating on Circuit Avenue. Dress up in your best costume and join the parade of ghosts, goblins, and ghouls as you collect sweet treats from local shops and businesses.
Oak Bluffs Turkey Trot (Thanksgiving Morning)
Start your Thanksgiving Day with a burst of energy at the Oak Bluffs Turkey Trot! This 5K road race takes runners through the scenic streets of Oak Bluffs, offering a fun and invigorating way to kick off the holiday.
Stay at Surfside Hotel
Enjoy the Martha’s Vineyard fall events and book a room at Martha’s Vineyard Surfside Hotel when planning to visit! Nestled in the heart of Oak Bluffs, our dog-friendly hotel is one of the premier lodgings in the area. Choose from accommodations with ocean-view rooms, garden views, modern amenities, and enough space for the entire family. We are a short four-minute walk from Ocean Park and a convenient location for exploring the rest of the island!
Our seaside accommodations are proud to be family-owned and operated since 1987. We look forward to welcoming you and your family to your home away from home at Martha’s Vineyard Surfside Hotel. Book your vacation with us today!


