Don’t Miss Events: May – June 2023

May, June: Polly Hill Arboretum, West Tisbury
Discover unique trees, cones, berries, and blooms in the spring season by taking a stroll through the beautiful historic grounds at Polly Hill Arboretum. Guided tours, scavenger hunts, and other activities are often available, and pamphlets can be picked up near the visitor center, which is on a bus route off State Road. To learn more, check or call 508-693-9426.

May, June: 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

May, June: Island Alpaca, Oak Bluffs
Spend some time with adorable and gentle alpacas and learn more about these curious creatures, including where they come from, their interesting behaviors, and why they are important. To find out what this unique farm has to offer, such as fun classes, events, and a gift shop, visit or call 508-693-5554.

May, June: Martha’s Vineyard Playhouse, Vineyard Haven
Enjoy stage plays, live music, poetry, art exhibits, classic films, and much more at the Island’s only professional year-round theater. M.V. Playhouse is located on Church Street, just around the corner from Main Street. For the latest information, visit or call 508-696-6300.

May 12–14: 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, refreshments, a dog show, plant sales, raffles, a 5K run/walk, and much more. For the full schedule, see

May 25–28: 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

May 27–28, June 11, 18, 25: 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 11, and every Thursday starting July 6. For details, visit

Starting May 28, 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

June: Drive-in Movies, Circuit Arts and YMCA, Oak Bluffs
Enjoy an old-fashioned drive-in movie experience, complete with live music and food trucks. Circuit Arts and 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

June: 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

Starting June 10, 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, 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

June 16–18: 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

June 17: 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

Starting June 17, 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 setting at 142 North Road. It is open from 9 am to 2 pm, with free entry and parking. For updates, check

June 22–25: Filmusic Festival, Film Center, Vineyard Haven
Watch feature films and musical performances come together in a celebration of culture, movies, and music. This 11th annual festival is presented by the M.V. Film Society. For the lineup, visit

Starting June 26, 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 schedule, visit