Tuesday, June 24, 2025
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    Festival round-up

    If you think the Martha’s Vineyard season ends after August — think again. From beer, food, wine, and chocolate, there are plenty of themed festivals that extend the local season well into the fall and winter. Checkout this round-up of Island festivals, and we’ll see you there! 

    Tivoli Day: Saturday, Sept. 14
    10 am – 6 pm; Circuit Ave., Oak Bluffs
    The celebration of summer’s end and beginning of the shoulder season. Join this annual event for food, shopping, music, face painting, and more. oakbluffsmv.com.

    Martha’s Vineyard Striped Bass and Bluefish Derby: Sept. 15- Oct. 19
    Now in its 74th year, “the Derby” is a beloved Vineyard fishing tradition wrangling anglers from all walks of life. mvderby.com.

    Martha’s Vineyard Craft Beer Festival: Saturday, Sept. 21
    12:30 – 7 pm; Waban Park, Oak Bluffs
    If you love beer, you’re going to love this event. Join the fourth annual Craft Beer Festival, featuring over 150 brews, ciders, wines, and more. mvcraftbeer.com.

    Art of Chocolate Festival; Oct. 12-13
    12-4 pm; Featherstone Center for the Arts, Oak Bluffs

    Taste chocolate concoctions made by Island bakers, artist, and chocolate lovers for the 18th annual chocolate festival. featherstoneart.org.

    Vineyard Artisans Columbus Day Festival; Sunday, Oct. 13
    10 am – 4 pm; Grange Hall, West Tisbury
    Catch all your favorite Island artisans for this one-day only festival. Weaving, fine furniture, pottery, leather goods, oil paintings, pastels, mixed media, sculpture, wampum, and more. vineyardartisans.com.

    Native Earth Popcorn Festival; Sunday, Oct. 13
    10 am – 3 pm: Native Earth Teaching Farm, Chilmark
    Family, fall, farm fun. Free popcorn for all. nativeearthteachingfarm.org.

    Morning Glory Pumpkin Festival; Saturday, Oct. 19

    11 am – 3 pm; Morning Glory Farm, Edgartown

    Rain or shine, the annual Pumpkin Festival is a free celebration for all ages. Games, hay rides, face painting, live music, and more. morninggloryfarm.com.

    Ladyfest: Saturday, Oct. 19
    5 pm – 1 am; the Ritz, Oak Bluffs
    A night of female-fueled music to raise awareness and funding for Connect to End Domestic Violence on Martha’s Vineyard. Live music and dancing all night. theritzmv.com.

    Martha’s Vineyard Food & Wine Festival; Oct. 23-27

    Four days and four nights of unique-to-the-Island food experiences. The annual festival invites you into the local culinary talent of farmers, fishermen, oyster producers, chefs, and artisans. mvfoodandwine.com.

    Women in Film Festival; Oct. 25-27
    M.V. Film Society, Vineyard Haven
    First annual Women in Film Festival is a celebration of women in front of and behind the camera. This festival will feature stories that haven’t been told from a woman’s perspective. mvfilmsociety.com.

    Felix Neck Fall Festival; Friday, Nov. 29
    11 am – 3 pm; Felix Neck Wildlife Sanctuary, Edgartown
    This celebration of fall is a Vineyard tradition held the day after Thanksgiving, drawing hundreds of Islands and visitors every year. Food, hayrides, face painting, music, and food. massaudubon.org.

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