2019: Annual can’t-miss events on Martha’s Vineyard

Fireworks over Ocean Park in 2019. —Gabrielle Mannino

April 7- May 5: Silver and Gold Art Exhibit, Featherstone Center for the Arts, Oak Bluffs. Golf leaf, silver gelatin prints, metal art, gold pendants, silver bracelets, and more. The “ores of the earth” serve as inspiration for this annual show. All media will be showcased. Opening reception is Sunday, April 7, from 4 to 6 pm.

April 12-14: Wicked Good Musical Revue, Martha’s Vineyard Playhouse, Vineyard Haven. Singer, composer, and musician Molly Conole leads this group of talented and enthusiastic singers in musical revues that feature a selection of songs with a common theme. Friday and Saturday performances at 7 pm, Sunday performance at 2 pm.

April 20: Vineyard Conservation Society’s Earth Day Beach Cleanup, beaches across the Island. Join friends and neighbors for the 27th annual Earth Day Beach Cleanup. Head out to your favorite beach and volunteers will be there with all the necessary cleanup materials. Afterward, join VCS for lunch at the Sailing Camp Park in Oak Bluffs.

April 25-28: Spectrum Film Festival, MV Film Society, Vineyard Haven. The Martha’s Vineyard Film Society presents the 3rd annual Spectrum Film Festival — a world perspective on LGBTQ+ stories, people, and issues through a variety of films and includes guest speakers, discussions,  and a special event for LGBTQ+ youth.

May 4: Ride the Vineyard MS Cycle Race, starting line at MVRHS. An extraordinary experience marked by passion, inspiration, determination and fun. Choose between 18-, 30-, and 60-mile routes, all to benefit the National Multiple Sclerosis Society.

May 10-12: Pink and Green Weekend, various locations in Edgartown. Kick off spring in Edgartown during the annual celebration of the spring season and Mother’s Day on Martha’s Vineyard. Enjoy the Pink & Green Dog Show, sales and shopping specials, Fairyville at Donaroma’s, the Pink & Green 5K and more.

May 11: MV Mini Maker Faire, Ag Hall, West Tisbury. Enjoy a showcase of Vineyard-made arts and crafts, science, and engineering, food and music, fire and water. Maker Faire is a show-and-tell format for people of all ages that brings out the “kid” in all of us.

May 12-27: Art of Flowers, Featherstone Center for the Arts, Oak Bluffs. The age-old tradition continues at Featherstone of ringing in spring by filling the main exhibition room with paintings, drawings, sculptures, and pretty much anything you can think of, all centered around beautiful blooms. This year’s gallery will feature special guest Holly Alaimo.

May 18: MV Marathon and Half Marathon, at MVRHS. Both the full and the half marathon are relatively flat with a few gentle rollers in the full marathon. Whether you’re trying to qualify for Boston or just want to run a beautiful race, see why Martha’s Vineyard is so famous and a spend a few extra days pre- or post- race.  A destination favorite!

May 23-26: MV Environmental Film Festival, MV Film Society, Vineyard Haven. For four days, The MV Film Society will combine environmental films, discussions, and an art exhibit by MVRHS students that will adorn the walls of the Feldman Family Art Space in the Film Center. A Q&A follows each film with experts, community members, and special guests.

May 25, 26: Vineyard Artisans Festival, Grange Hall, West Tisbury. The opening show of the season. Come and see all the new work our Island Artists have been working on all winter, great food, free parking and admission, catered food, many demonstrations, and a playground for kids.

May 26: Memorial Day Road Race, Summercamp Hotel, Oak Bluffs. 26th annual 5K around Oak Bluffs harbor and East Chop Lighthouse. Timed 1-mile kids’ fun run. Online registration is $25, in-person registration is $30, open Saturday, 3 pm to 5 pm and day of the race from 8 am to 9:30 am. All proceeds to benefit Hospice of Martha’s Vineyard.



June 13, 15: Taste of the Vineyard, Dr. Daniel Fisher House, Edgartown. One of the most anticipated events of the year, the Taste of the Vineyard kicks off the social season with great wine tastings and food in a posh, pinkies-out environment. What started as a small potluck has now turned into a central event and fundraiser for the Vineyard Trust, which seeks to preserve some of the most historical landmarks on-Island. Tickets are $175 each, and boy, do they go quick.

June 20-23: Filmusic Festival, MV Film Society, Vineyard Haven. Music and film flow naturally together. The 7th Annual Filmusic Festival will bring you closer to the music you love, or introduce you to some you’ve never known, with great films and live music.

June 22: Harbor Festival, Oak Bluffs Harbor, 10 am- 6 pm. Live music, food, arts, crafts, Rain date June 23.  

July 4: Annual Kid’s Parade, Oak Bluffs. Open to all Island children and their parents. Begins on West Clinton Avenue. No motorized scooters, bikes, etc., please. Followed by an ice cream social under the tent.

July 4: Parade and Edgartown Harbor Fireworks, downtown Edgartown. The parade begins at 5 pm, and fireworks start at dusk on the harbor.

July 12-14: Vineyard Cup Regatta, Vineyard Haven. A full weekend of racing, socializing, and dining, benefiting Sail Martha’s Vineyard.

July 17-20: Blue Water Classic Fishing Tournament, Oak Bluffs Marina. This annual event welcomes fishing enthusiasts with vessels that have the range to fish in the vicinity of northeast canyons, raising funds for the Island Autism Group of Martha’s Vineyard and the MGH Colon Cancer Research Fund in memory of Kevin Glynn.

July 20: Featherstone Center for the Arts Gala, Oak Bluffs. Enjoy artwork, cocktails, hor d’oeuvres, dinner, and silent and live auctions on the grounds outside the Art Barn. Proceeds from the event benefit Featherstone’s year-round programming and community outreach.

July 21, 22: Portugese Holy Ghost Feast & Festival, Portugese American Club, Oak Bluffs. Parade, auction, food, music, dancing, games, and fun for all ages.

July 28: Possible Dreams, Tilton Farm, Chilmark. Support Martha’s Vineyard Community Service’s largest annual fundraiser. This year’s event is making the move up-Island and will feature live music, an online Super Dreams auction, the 12 Dreams of Summer (our live auction), a raffle and much more. Possible Dreams highlights the passion and dedication of Island community, staff, volunteers, sponsors, donors, and everyone who makes each event so special.

August 2-4: Martha’s Vineyard Book Festival, Chilmark Community Center. This annual book festival returns for its eighth season. Set in spectacular locations across Martha’s Vineyard, this year’s lineup includes Pulizer and National Book awardwinners, plus many New York Times best sellers.

August 5-9: Martha’s Vineyard Documentary Film Week, Martha’s Vineyard Film Center, Oak Bluffs. Documentary films have become the conscience of the nation, providing a deeper study of contemporary, and often unnoticed, social issues. The M.V. Film Society presents Doc Week in collaboration with HBO Documentary films on recognition of the rising importance of documentaries to public dialogue.

August 8-11: Built on Stilts, Union Chapel, Oak Bluffs. Celebrating its 22nd year, Built on Stilts is the Vineyard’s own community dance festival, offering up a different show each night. Free and for all ages.

August 11, 12: Islanders Write, Presented by The MV Times, Featherstone Center for the Arts, Oak Bluffs. An evening panel discussion on Sunday night followed by a full day of panel discussions, workshops, author signings, and readings.

August 14: The Grand Illumination of the Oak Bluffs Campground, a.k.a. “Illumination Night,” the Tabernacle, Oak Bluffs. The iconic gingerbread cottages will be adorned with colorful Chinese and Japanese lanterns, which will be lit at dark. A Community Sing will precede the Grand Illumination, and the Vineyard Haven Band will play at the Tabernacle at 8 pm. The event is open to the public with a suggested freewill offering.

August 15-18: 158th Annual Martha’s Vineyard Agricultural Fair, Agricultural Hall, West Tisbury. Rides, games, live music, livestock, competitions, craft demonstrations, food, shopping, art show, and awards for homegrown vegetables, fruits, flowers, and homemade goodies.

August 16: Band Concert and Fireworks, Ocean Park, Oak Bluffs. Hosted by Oak Bluffs Fireman’s Civic Association. Band performance starts at 8 pm, and fireworks will light up the sky around 9 pm.

Sept. 3-8: Martha’s Vineyard International Film Festival, Martha’s Vineyard Film Society, Vineyard Haven. The 2019 Martha’s Vineyard International Film Festival will present a selection of films from around the globe by International filmmakers. Films drawn from top-notch festivals like Sundance, Berlin, and Cannes, with a few surprises thrown in.

Sept. 7: Annual Wind and Kite Festival, Ocean Park, Oak Bluffs. Free kitemaking and kite-flying competition for kids and adults. Plus Frisbee games, model sailboat racing, live music, bubbles, and more.

Sept. 14: Tivoli Day Festival, Circuit Ave., Oak Bluffs, 10 am- 6 pm. The Oak Bluffs Association holds its annual Tivoli Day celebration, featuring live outdoor music all day, as well as food and retail vendors set up on the street, and special sales and events in nearby Oak Bluffs stores. Circuit Avenue will be closed to traffic during the event, which celebrates the end of the summer and the beginning of the Island’s shoulder season. Rain date Sept. 15.)

Sept. 15- Oct. 19: Martha’s Vineyard Striped Bass and Bluefish Derby, For over 70 years, “the Derby” has been a time to renew friendships, share a cup of coffee, and create memories that fuel the winter’s exaggerated fishing stories. It is a time when all are able to refocus on the natural beauty of this Island sanctuary.



Oct. 23-27: Martha’s Vineyard Food & Wine Festival, Edgartown. The Martha’s Vineyard Food & Wine Festival invites you a four-day feast celebrating the Vineyard’s best culinary talent — and the farmers, fishermen, oyster producers, and artisans they work with — paired with guest chefs and vintners from around the world for a unique-to-the-Island experience.

Oct. 26: Halloween in Oak Bluffs, Trick-or-treating on Circuit Ave. Free.

Dec. 12-15: Christmas in Edgartown. A winter weekend festival not to be missed, including family-friendly events that capture the magic of the holidays.