Embracing the Colors of Autumn: A Guide to Fall Events on Martha’s Vineyard

As the summer crowds disperse and the Island’s landscape transforms into a picturesque tapestry of vibrant hues, Martha’s Vineyard enters a new chapter of its annual charm with a delightful array of fall events. This quintessential New England destination offers a unique blend of cultural celebrations, outdoor festivities, and culinary experiences during the autumn season. From international film showcases to kite-filled skies, from competitive fishing derby to delicious gastronomic adventures, Martha’s Vineyard becomes a haven for both locals and visitors. In this blog post, we’ll explore some of the best fall events that make this Island an enchanting destination during the autumn months.

Sept. 3: MV SOUNDFEST, Family-Friendly Festival at The Cove

On Sunday, September 3, MV SOUNDFEST, a musical mashup of reggae, rock, soul, and more will be held behind The Cove Golf & Grill in Vineyard Haven. MV SOUNDFEST will feature a diverse lineup of talent including renowned reggae music headliner Anthony B, as well as local acts, Workman Song, Rose Guerin, Dock Dance Band, DeeJay Supa Ricky Prime & DJ D-DUB. Vermont-based hip hop  Mister Burns will be joining with a one-man show and a very special guest act to be announced. Bring the family (kids 12 and under are free!) for a full day of fun and entertainment this Labor Day weekend!

Sept. 5–10: Martha’s Vineyard International Film Festival, Celebrating Cinematic Art 

Kicking off the fall season is the Martha’s Vineyard International Film Festival. Film enthusiasts gather to immerse themselves in a curated selection of thought-provoking, diverse, and inspiring films from around the world. The festival not only showcases cinematic artistry but also fosters discussions and interactions among filmmakers and audiences through panels, workshops, and Q&A sessions. This year the festival will be held on September 5-10 at the Martha’s Vineyard Film Center. With films from Switzerland, Italy, Mexico, and more, there is something for all interests! Explore the films and purchase tickets here

The Martha’s Vineyard wind Festival comes to Oak Bluffs’ Ocean Park each September.

Sept. 9: Wind and Kite Festival, A Sky Full of Colors

Against the backdrop of the Island’s stunning coastline, the Wind and Kite Festival paints the sky with an array of vibrant kites. Families come together to fly kites of all shapes and sizes, creating a mesmerizing spectacle against the autumn skies. This event embodies the joy of simple outdoor pleasures and offers a sense of childlike wonder to attendees of all ages. The Kite Festival will be on Saturday, September 9th in Ocean Park, and you can learn more on their website! We recommend packing a picnic, or grabbing food from one of the incredible restaurants in Oak Bluffs and spending the day in the park enjoying the views! 

Sept. 10–Oct. 14: Fishing Derby, A Test of Angling Skills 

For those with a passion for fishing, the Martha’s Vineyard Striped Bass and Bluefish Derby is a fall event not to be missed. Anglers of all levels compete in this challenging yet exhilarating competition to catch the biggest fish. With a sense of camaraderie and a dash of friendly rivalry, participants cast their lines into the Island’s waters in hopes of reeling in a remarkable catch. Locals joke that they won’t see their partners for the whole month, and the beaches and bridges will be scattered with hopeful fishermen. This year marks the 78th annual derby, and the dates are September 10 to October 14. If you’re not interested in casting a line, we recommend visiting one of the daily weigh-ins, to take a look at the catch of the day! Weigh-ins are at the Edgartown Harbor in front of the Atlantic, from 8am-10am and 7pm-9pm. Learn more and sign up by visiting their website

The MV Striped Bass & Bluefish Derby attracts anglers from all over each fall.

Sept. & Oct.: Bass in the Grass, Art For A Noble Cause

The Edgartown Board of Trade presents the 6th annual Bass In the Grass Fundraiser, a tribute to the Martha’s Vineyard Striped Bass & Bluefish Derby of the fall of 2023. This remarkable initiative not only resonates with the Island’s rich angling heritage but also serves as a platform for raising funds to support local artists, the Edgartown Board of Trade (EBT), and the Derby Scholarship Fund. Running from mid-September through October 15th, this event offers a unique chance to secure your own piece of the Island’s heritage. Take part in the excitement by participating in the bidding process for your favorite Bass during the derby’s duration. Starting Friday, September 22nd, visitors are invited to admire these pieces of art at The Carnegie Heritage Center. Make sure to visit their website for more information.

Sept. 16: Tivoli Day, Embracing Autumn with a Time-Honored Celebration

Bid farewell to summer as you embrace the cherished tradition of Tivoli Day, a lively September street fair and block party in downtown Oak Bluffs that has graced Martha’s Vineyard for over four decades. A day of revelry dedicated to acknowledging the summer’s diligent efforts and ushering in the picturesque Island autumn. The festivities encompass live entertainment, street vendors, music, dancing, arts, irresistible end-of-summer sales, and an array of delectable cuisines, marking a vibrant and heartwarming welcome to the season ahead. Head to the festival on September 16th from 10am to 6pm in Oak Bluffs and shop those end-of-season sales!

The Martha’s Vineyard Food & Wine Festival returns after a three-year hiatus. Photo by Vineyard Lights.

Oct. 19–22: Return of the Food & Wine Festival, A Gastronomic Affair

Foodies and wine connoisseurs rejoice as the Food & Wine Festival returns on October 19th to the 22nd to tantalize taste buds. Renowned chefs, sommeliers, and culinary experts gather to present a symphony of Martha’s Vineyard flavors, highlighting the Island’s rich culinary heritage. From exquisite wine tastings to gourmet dinners, this event promises a delectable journey through Martha’s Vineyard’s gastronomic landscape. Dine at some of the best restaurants on the Island, from Bettini to Atria, to the Dunes and Red Cat, each chef will be preparing something unique and inspiring! Visit their website to explore the different events and chefs and purchase your tickets! You can read all about our experience at the 2019 festival on the blog here.

Oct. 21: Brunch Run, Where Fitness Meets Flavor 

Combining exercise with indulgence, the Brunch Run offers a unique blend of fitness and flavor. On October 21 at 8am, participants engage in a scenic run through the Island’s picturesque trails, followed by a well-deserved brunch. This race is hosted by the Edgartown Board of Trade and has both a 5k and 10k course through Edgartown. This event encapsulates Martha’s Vineyard’s commitment to a healthy lifestyle and a celebration of its natural beauty. Register for the race here

As summer makes way for autumn, Martha’s Vineyard transforms into a captivating haven of fall events that celebrate culture, community, and creativity. From the allure of international films to the joy of kite-filled skies, from the thrill of fishing competitions to the indulgence of gourmet delights, the Island offers an enchanting array of experiences that capture the essence of this vibrant season. Whether you’re a film buff, an outdoor enthusiast, a culinary adventurer, or someone seeking unique local crafts, Martha’s Vineyard’s fall events promise to leave an indelible mark on your heart and memories that will last a lifetime.

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