May 6–8: Pink & Green Weekend, Edgartown
Celebrate the spring season and Mother’s Day in a family friendly annual festival in picturesque Edgartown. Enjoy horse-drawn carriage rides, pop-up shops, brunches and luncheons, goodie bags, store specials, snacks and refreshments, a dog show, plant sales, raffles, a 5K run/walk, and much more. For the full schedule, see edgpinkandgreen.com.
May 6–8: SPECTRUM Film Festival, Film Center, Vineyard Haven
This innovative festival offers a variety of films that give a global perspective on LGBTQ+ stories and issues. It also includes guest speakers, discussions, and a special event for youth. For the program schedule, check mvfilmsociety.com.
May 18–22: Martha’s Vineyard Film Festival, Grange Hall, West Tisbury
Watch curated films from around the world in the 22nd annual M.V. Film Festival, which takes place in its new home in the Grange Hall’s upstairs theater. MVFF screens movies that can inspire, educate, spark discussion, and strengthen the community. For more details and the film lineup, visit tmvff.org.
May 26–29: Environmental Film Festival, Film Center, Vineyard Haven
Enjoy inspirational and engaging films with an environmental theme, presented by the M.V. Film Society and the Vineyard Conservation Society. The thought-provoking movies explore humanity’s relationship with the natural world. Check the festival schedule at mvfilmsociety.com.
May 28–29, June, July: Vineyard Artisans Festival, Grange Hall, West Tisbury
Meet more than 70 local artisans, buy directly from them, and see demonstrations of fine art and crafts. Discover furniture, pottery, stained glass, paintings, sculpture, jewelry, quilts, handmade books, and much more. This annual tradition is open Memorial Day weekend, every Sunday starting June 12, and every Thursday starting July 7. For details, visit vineyardartisans.com.
Starting May 29, Sundays: Oak Bluffs Open Market, Washington Park
Shop for Island-grown produce, original artwork, handmade jewelry, fine crafts, summer flowers, specialty foods, and vintage finds in an open market near Oak Bluffs Harbor. It is like a farmers market, antique show, artisan fair, and a body/mind/spirit expo all in one, plus live music. For the schedule, visit facebook.com/oakbluffsopenmarket.
May, June, July: Magical Sculpture Trail, Island Folk Pottery, Chilmark
Walk along a quarter-mile enchanting trail through the woods and discover whimsical sculptures on the way to an Island Folk Pottery shop. Created by artists Bill O’Callaghan and Heather Goff, the path is open daily from 9 am to 5 pm. Their pottery studio is open Wednesday to Saturday, 11 am to 5 pm, and Sundays, 2 to 5 pm. To learn more, visit islandfolkpottery.com.
Starting June 11, Sat. and Wed.: West Tisbury Farmers Market, Agricultural Hall
The Island’s oldest and largest farmers market features locally grown, seasonal produce, as well as homemade bread, savory condiments, fresh honey, homemade jams, beautiful flowers, artisan chocolates, sweet desserts, and unique gifts. Before visiting this popular market, review the shopping guidelines at wtfmarket.org, and consider preordering online.
June 16, 18: Taste of the Vineyard, Daniel Fisher House & Gardens, Edgartown
Sample a variety of local foods at the Gourmet Stroll on June 16, featuring the Island’s finest restaurants and caterers. Then on June 18, enjoy an evening of cocktails, arcade games, a silent and live auction, and a catered dinner at the Patrons’ Party and Auction. Find all the details at vineyardtrust.org/upcoming-events.
June 17–19: Blooming Art, M.V. Garden Club, West Tisbury
This delightful springtime show pairs the work of Vineyard artists with the floral designs of M.V. Garden Club members who were inspired by the art. All of the artwork and flower arrangements are for sale. It takes place in a beautiful setting at the Old Mill, which is across from Mill Pond. For more information, visit marthasvineyardgardenclub.org.
June 18: HarborFest, Oak Bluffs
Kick off the summer season with a fun-filled harborside festival in Oak Bluffs. Celebrate with live music, food, art, crafts, and shopping from local vendors. This annual one-day event is from 9 am to 7 pm along Lake Ave. For the latest information, check obamv.com.
June 23–26: Filmusic Festival, Film Center, Vineyard Haven
Watch feature films and musical performances come together in a celebration of culture, movies, and music. This 10th annual festival is at the M.V. Film Center and online. For the full lineup and the schedule, visit mvfilmsociety.com.
Starting June 25, Wed. and Sat.: Chilmark Flea Market
Visit the oldest outdoor flea market on the Island, offering antiques, imports, vintage finds, and high-quality handmade items from Vineyard artists and craftsmen. Discover jewelry, clothing, art, food, and much more, all in a beautiful outdoor setting at 142 North Road. It is open from 9 am to 2 pm, with free entry and parking. For updates, check facebook.com/chilmarkflea.
June and July: Drive-In Movies, MVFF and YMCA, Oak Bluffs
Enjoy an old-fashioned drive-in movie experience, complete with live music and food trucks. The M.V. Film Festival and the YMCA of M.V. are showing feature films on a large screen in the parking area behind the M.V. Ice Arena. To view the movie schedule, visit driveinmv.com.
Starting July 1, Mon. and Fri.: Outdoor Concerts, Featherstone, Oak Bluffs
Enjoy musical performances on the beautiful lawn surrounding the Art Barn’s deck. All tickets for the performances will be sold online starting at 12 pm the week prior to a concert. The lineup includes Johnny Hoy and the Bluefish, Jon Zeeman, Grateful Dread, and much more. For the full schedule, visit featherstoneart.org/music.html.
July 7, 9–10: Seafood Buffet and Auction, Vineyard Cup Regatta, Vineyard Haven
Along the Tisbury waterfront, enjoy seafood, refreshments, live entertainment, views of beautiful sailboats, and a chance to win local experiences and products. The Sail MV buffet and auction are on July 7, and the regatta takes place from July 9–10. To learn more, visit sailmv.org.