The Art of Flowers: Creativity in Bloom Opening Reception - Sunday, May 3rd from 4:00pm to 6:00pm - Our annual Art of Flowers show returns this May! Join us for Creativity in Bloom, a celebration of vibrant colors and warmer days as the world blossoms into spring. From wildflowers to garden favorites, there is inspiration to be found everywhere. Light refreshments will be served.
Locals: A Two-Night Festival of Vineyard Talent - Friday & Saturday, May 1st & 2nd at 7:00pm - Locals is a two-night mini-festival featuring live performances by the Vineyard community, including music, theater, dance, spoken word, and improv. Now in its fourth year, the festival offers a welcoming space for artists to share new work and connect with audiences.
Paleface and Mo Live in Oak Bluffs - Friday, May 1st from 7:00pm to 9:00pm - Paleface is a prolific American songwriter and recording artist currently performing as a dynamic acoustic-electric duo with his Puerto Rican drummer and partner, Mo.
Maypole Celebration - Saturday, May 2nd at 11:00am - Join the Friends of the West Tisbury Village for a Maypole Celebration on the Field Gallery Lawn! Snacks and crafts after on the library’s porch. For all ages!
4-H Farm Animal Meet and Greet - Sunday, May 3rd from 10:00am to 12:00pm - Meet Island farm animals, from calves to pigs to goats, at our annual fundraiser for Martha's Vineyard 4-H! This event is good for the whole family and all funds raised will support Martha's Vineyard 4-H. COST: $5 kids, $2 adults. Pay cash or card at the door!
Growing Tomatoes with Lydia Fischer - Tuesday, May 5th from 5:30pm to 7:00pm - In this talk, Lydia Fischer, owner of The Garden Farm, will share everything you need to know to successfully grow tomatoes: place and time to plant, diseases or pests to look out for, benefits of pruning, favorite varieties, trellising suggestions, and more. There will then be time for Q and A! COST: FREE and open to all, from beginner to experienced gardeners. Registration helpful. Sign up on our website!
Community Greenhouse Annual Sale - Saturday, May 9th from 10:00am to 3:00pm - Community Greenhouse Annual Plant Sale! We have beautiful annuals and perennials for your gardens.
Minnesingers Spring Concert - Saturday, May 9th from 7:00pm to 8:30pm & Sunday, May 10th from 2:00pm to 3:30pm - The Minnesingers of Martha's Vineyard Regional High School present their annual spring concert—a lively and entertaining performance featuring a mix of choral music, movement, and student talent. This year’s concert follows the group’s recent silver medal win at the MICCA Festival and their upcoming performance tour in Northern Italy. Known for their energy, musicality, and strong sense of community, the Minnesingers offer a show that is both polished and fun.
An Evening of Comedy with Ophira Eisenberg - Sunday, May 10th at 7:00pm - Ophira Eisenberg is a stand-up comedian, writer, and podcast host whose comedy has been featured on NPR, HBO, Comedy Central, CBS, and The Moth. A former host of NPR’s Ask Me Another, she headlines theaters worldwide, tours with The Moth Mainstage, and hosts the parenting comedy podcast Parenting Is a Joke. Her newest comedy special, produced by Lewis Black, premieres in spring 2026.
Archaeology I.D. Day - Saturday, May 16th from 2:00pm to 4:00pm - The West Tisbury Library will host its seventh annual Archaeology I.D. Day. All are invited! Please bring any artifacts you may have discovered for expert identification and discussion. The archaeologists present will be happy to answer any questions about the archaeology of Martha’s Vineyard and about New England in general. There will also be informative displays to be viewed. On hand for the event will be archaeologists Duncan Caldwell and Bill Moody. This event is free and open to the public.
Open Mic Night - Tuesday, May 5th at 6:00pm & Tuesday, May 19th at 6:00pm - With the closure of Island Music, Open Mic Nights are now co-hosted by Vineyard Haven Public Library and the Vineyard Haven Harbor Cultural District at the Katharine Cornell Theatre. Come to play, or just to listen. Sign-up on arrival, free and open to all!
Historic Cemetery Tour with Tom Dresser - Wednesday, May 20th from 9:00am to 10:00am - Join local historian Tom Dresser for a fun, informative & not-at-all-scary cemetery tour. We will meet outside at Pacific Avenue entrance (cemetery-facing side) of the Oak Bluffs library. Tour takes about an hour and is about a mile in distance.
Weather dependent. Call 508-693-9433 or email oakb_mail@clamsnet.org for more information.
Found Foods Supper Club: A Hands-On Culinary Experience - Thursday, May 21st from 5:30pm to 7;00pm - Join Chef Jenny DeVivo for a unique hands-on culinary experience that celebrates food rescue, zero-waste cooking, and seasonal ingredients from local farmers, fishers, and food purveyors. Each session features a curated, on-the-spot menu dictated by the surplus ingredients available that week—transforming overlooked foods into delicious, sustainable meals. Attendees will actively participate in cooking, learning upcycling techniques, and gaining practical culinary skills, all while taking home their homemade dishes to enjoy with family and friends. Pre-registration required for all Farm Institute cooking classes.
Martha’s Vineyard Garden Club Annual Plant Sale - Saturday, May 23rd from 10:00am to 2:00pm - Celebrate the season with us and discover a wonderful selection of plants grown and selected by our members. From colorful perennials and herbs to unique garden favorites, you’ll find something special to bring home to your garden. Your purchase supports the programs, education, and beautification projects of our Garden Club. Come browse, ask questions, and enjoy a morning surrounded by plants and fellow garden lovers.
32nd Annual Martha's Vineyard Memorial Road Race - Sunday, May 24th from 10:00am to 12:00pm - Join us for the 32nd Annual Martha's Vineyard 5K Memorial Road Race to support Hospice and Palliative Care of Martha's Vineyard on Sunday, May 24th! Participants can run or walk a beautiful USATF-certified course around Oak Bluffs harbor and East Chop Lighthouse, beginning at 10:00AM. There is also a 1-mile kids’ fun run that starts in front of Summercamp Hotel at 9:30AM. Sign up today - there is a limited supply of NEW T-shirts available! Online registration is $30 and day-of registration is $35. Sign-up here! Bib pick-up and check-in will take place on Saturday, May 23rd from 3-5PM & Sunday, May 24th from 8-9AM at Summercamp Hotel.
Live Band Karaoke with Agreeable Men - Tuesdays in May at 9:00pm - Bring your lead singer energy to The Ritz and sing along with Agreeable Men! Over 400 songs available to choose from. Your time to shine, every Tuesday night at 9 p.m.
Friday Game Time at the Museum - Fridays in May from 1:00pm to 4:00pm - Friday Game Time at the Museum takes place every Friday from 1 to 4 p.m. in the museum’s First Light Café. Stop by for a relaxed afternoon of board games and card games in a welcoming, drop-in setting designed for all ages. Bring a friend, join a table, or settle in with a game and enjoy the easygoing atmosphere of the Café. This program is free and open for all to attend. Pay-what-you-can donations support Museum programs.
Tyke Hikes at Felix Neck - Saturdays in May from 9:30am to 10:30am - Skip, waddle or walk with your little ones alongside a Naturalist as you explore a new habitat on this one-hour program. From the field to the pine forest to the shoreline-each trek brings a new adventure! See the season unfold on the trails as you search for wildlife and explore different habitats!
The Pawnee House Presents Blues Duo - Saturdays in May from 6:00pm to 8:00pm - The Blues Duo returns to The Pawnee House Restaurant, Special Date, Saturday, May 2, 2026. Thereafter every Thursday. Singing and playing a "Soulful Harmonica" totally unplugged, accompanied by a low volume guitar. Got that New Orleans feel. Check it live!
Fly Rod Striped Bass Catch and Release Tournament - Saturday, May 30th from 7:00pm to 12:00am - A one-night team shore fly fishing contest defined by fishing camaraderie. The tournament rules are based on teams filling their fish quotas in the shortest time. Plaques are awarded based on each qualifying team's earliest finish time.