The Vineyard in October is nothing short of magical. Enjoy the warm daylight with a serene sea-glass hunt along quiet shores or an amazing visit to the extraordinary MV Museum. Then enjoy the crisp evenings for a perfect night out at one of the many delicious restaurants, live music, and cozy fireside relaxation. This island has so much to offer this fall. Here’s our guide to the must-do events on the Vineyard this October. “Autumn is a second spring when every leaf is a flower.” Albert Camus.
- It’s still Derby time! 2025 80th Anniversary Derby - Until Saturday Oct 18 - Come to the Vineyard and Fish the Derby! For eight decades, "The Derby" has been a time to renew friendships, share a hot cup of coffee and create memories that fuel the winter's exaggerated fish tales. It is a time for all to refocus on the natural beauty of this Island sanctuary. So come and join us, to experience great fishing, rich history, meeting new friends, and generous sponsor-donated prizes - all in support of our scholarship program.
- Cooper Gilkes & Nelson Sigelman: Fishing, Friendship & the Derby - October 1st from 5:30pm to 6:30pm - This fall, the Museum joins the Martha’s Vineyard Striped Bass and Bluefish Derby celebrating eight decades of fishing, community, and Island tradition. Through this special lecture series, hear directly from those who have lived the Derby—seasoned anglers sharing stories, memories, and the enduring connections forged along Vineyard shores. This evening, join longtime friends and Derby veterans, Cooper "Coop" Gilkes and Nelson Sigelman, who have spent decades casting lines and sharing stories on Martha's Vineyard. Coop, owner of Coop’s Bait & Tackle, is a fixture in the fishing community and has been instrumental in organizing the Derby and the Catch & Release Tournament. Nelson, a former editor at The Martha’s Vineyard Times, is an award-winning outdoor writer whose fishing columns have captured the essence of Island life.
- First Friday Vineyard Haven - Friday, October 3rd at 4:00pm - First Friday is a free community-inspired outdoor event in Vineyard Haven, Martha's Vineyard. Started in 2016 and based on the nation-wide First Friday art walks, we celebrate the local art and culture of our island.
- PA Family Day - October 4th from 1:00pm to 4:00pm - Food, games, music, costumes welcome!
- Ghosts, Gossip and Downright Scandal Walking Tours - October 3, 7, 10 & 14 from 5:00pm to 6:15pm - A light-hearted walking tour of historic Edgartown. Actual history of the town with four scandals, four ghost stories, and lots of gossip. If you are looking for the history of the town, its people, and its building, this is the right tour for you. If you are looking for scary ghosts, it is not. Reservations requested.
- History Matters: An Evening with the Words of David McCullough - October 9th from 5:00pm to 6:00pm - A conversation with Dorie McCullough Lawson, David McCullough’s daughter and editor of History Matters. Pulitzer Prizes. National Book Awards. Presidential Medal of Freedom. A voice that made history breathe. In this posthumous work, History Matters, drawn from McCullough’s lifetime of scholarship, we are reminded that history isn’t dusty dates, it’s human drama, lived courage, and the compass we use to navigate the present.
- Vineyard Artisans Fall Festival at the Union Chapel in Oak Bluffs - October 11th & 12th from 10:00am to 4:00pm - Catch all your favorite Island artisans! Weaving, fine furniture, pottery, leather goods, oil paintings, pastels, mixed media, sculpture, wampum jewelry, hand knit items, clothing, photography, handmade books and much more.
- 7th Annual Women in Film Festival - October 17th-19th from 4:00pm to 10:00pm - The Martha’s Vineyard Film Society is excited to present our 6th annual Women in Film Festival (WIFF) at the MV Film Center. WIFF is a celebration of women in film: both in front of and behind the camera. This festival features stories that have not usually been told from a woman’s perspective. On the big screen, WIFF will include six films featuring female characters who break the mold in as many genres as possible.
- The Sound of Jaws: John Williams and the Score That Changed Everything -October 23rd from 5:00pm to 6:00pm - Everyone knows the two terrifying notes that launched the Jaws theme—and with it, an entire era of cinematic sound. But what followed those notes transformed film music forever. Join us on Thursday, October 23 as acclaimed journalist and author Tim Greiving for a riveting dive into John Williams: A Composer’s Life, the first major biography of the man behind the music that shaped generations.
- Halloween in Oak Bluffs - October 25th - all day - Costumes, trick-or-treating, and more
- The Farmer and The Shark - October 25th from 4:00pm to 5:30pm - After two sold-out screenings, The Farmer & The Shark returns for one last encore. Don’t miss this final chance to experience the extraordinary Vineyard story of Craig Kingsbury and his unforgettable influence on Jaws.
- Howl-a-ween Bark and Boo Bash - October 31st from 12:00pm to 5:00pm - Howl-a-ween Bark and Boo Bash at the MV Chamber of Commerce! Join us in Vineyard Haven for a spook-tacular Halloween celebration! Bring your kids and pets for a day of fun and festivities: Costume Contest: Dress up your pups in their spookiest, funniest, or most creative costumes for a chance to win prizes! Categories include Best Overall, Most Creative, and Cutest Costume. Pet Photo Stop and Repeat: Capture the Halloween spirit with our themed photo display. Don’t forget to strike a pose with your four-legged friends against our spooky backdrop! Marilyn Roos Photography will be on site to capture all the fun! Trick or Treat Stations: Enjoy safe and fun trick-or-treating with special treats for both dogs and their owners. Plus, a portion of the proceeds will benefit Martha’s Vineyard Animal Shelter! Costumes encouraged—see you there!
- Bass in the Grass - Through October 19th - Be sure to bid on your favorite Bass by the end of the derby for a chance to have a piece of the island in your home. The Vineyard Preservation Trust is proud to host the 8th Annual Bass in the Grass Fundraiser at The Carnegie in partnership with the Edgartown Board of Trade. This creative community initiative honors the Martha's Vineyard Striped Bass & Bluefish Derby and supports local artists, the EBT, and the Derby Scholarship Fund, which benefits qualified Vineyard students annually.
- Kismet Outfitters Group Fly Casting Lesson - Wednesdays in October - Capt. Abbie Schuster, Kismet Outfitters owner, and head fly fishing guide, will be leading weekly fly-fishing casting classes at the Edgartown Lighthouse. All equipment is provided, and no experience is necessary. This is the perfect opportunity to learn the art of fly casting with a certified casting instructor.
- Blues Duo at the Ritz - Thursdays in October from 6:30pm to 8:30pm - This is an evening of Blues music! Jimmy Carnazza sings a cappella, while playing a soulful Harmonica, Larry Lusignan accompanies on lov vol. guitar