Karen M. Overtoom Logo
Your connection to all Martha's Vineyard Real Estate and Vacation Rentals
508-693-7832
Karen M. Overtoom Logo
508-693-7832

The Best of May, 2022 on Martha's Vineyard


The Vineyard is hopping this May! Lobster rolls, live music, artisan festivals, all we have been waiting for~finally, the summer we all deserve. Here are our picks for the top things to do in May on Martha’s Vineyard! 

  • Sunday, May 1st at 11:00am to 12:30pm - Music and discussion of Indigenous issues with David, Saskia, and Nanawue Vanderhoop - Music and discussion of Indigenous issues with David, Saskia, and Nanawue Vanderhoop.
  • Sunday, May 1st at 2:00pm - Wicked Good Musical Revue - A Tribute to Sondheim presented by some of the Vineyard's best performers. Audiences return to the Playhouse time and time again to brighten winter spirits. Masks required. Musical director: David Behnke. Accompanists: Peter Boak, Molly Sturges and Brian Weiland. Ensemble performers: David Behnke, Molly Conole, Rachel Cook, Jenny Friedman, Katherine Reid and Ken Romero. Purchase tickets at mvplayhouse.org.
  • Sundays in May from 8:00pm to 10:00pm - Live Music: Holy Rock and Roll Revival - Brothers Sean and Griffin McMahon provide music and comic relief at this feel-good performance.
  • May 1st through May 8th from 10:00am to 4:00pm - Wampum: Stories from the Shells of Native America - The Wampanoag people have lived in northeastern America for over 12,000 years. Their nation extended beyond Boston, into central Massachusetts, and south to Rhode Island. This exhibition unites contemporary indigenous artists and educators in retelling history from the indigenous perspective and through traditional art. Created as part of the commemoration of the 400th anniversary of the Mayflower voyage, the Museum is honored to host this traveling exhibition, which will be making its North American debut at the MVM after touring at venues across England. Exhibit open through May 8 during museum hours. For information and tickets, check mvmuseum.org. 
  • Tuesdays in May from 6:00pm to 8:30pm at Offshore Ale - Live Music: Jeremy Berlin - Jazz played by Jeremy Berlin on piano and Eric Johnson on guitar. 
  • Tuesday, May 3rd at 7:00pm to 8:00pm - Gypsy Belly Dance Workshop - Join Karam Belly Dance for a fun, three-week gypsy belly dance workshop.  For ages 18 and up. All sizes and skill levels are welcome! Skirts and coin belts will be provided for class use. Classes will be held in Vineyard Haven. Cost: $45 (for all 3 classes) due at first class. Register at betsy@vineyard.net
  • Tuesdays in May from 7:00pm to 9:00pm - Trivia Night at The Ritz Cafe         
  • Wednesdays and Saturdays in May from 10:00am to 1:00pm - Salt Rock Chocolate Spring Pop-Up - Come visit us at our spring pop-up at Beetlebung Farm, South Road entrance (across from the Chilmark Library). Available Wednesdays and Saturdays, 10 a.m. to  1 p.m. (or until sold out) No pre-orders or shipping at this time.  We accept Venmo, cash, check, credit card, Apple Pay
  • Thursday, May 5th at 5:30pm to 7:30pm - Tacos, Tortillas and Mocktail Margaritas - Celebrate Cinco de Mayo by learning tips and tricks to making the best (inauthentic) Mexican street fare that you can enjoy all year long! This class will feature a local menu with homemade flour tortillas, Slough Farm beef and Farm Institute pork taco fillings, and of course, a margarita mocktail to wash it all down with. Led by Chef Charles Grandquist. Member: $32; non-member: $40; pre-registration is required at thetrustees.org for all Farm Institute cooking classes. Please contact Lindsay with any allergy or food restriction questions at lbrown@thetrustees.org 
  • Thursday, May 5th at 6:00pm - The Buzz about Honeybee Keeping in Massachusetts - Chief apiary inspector Kim Skyrm will speak about beekeeping in Massachusetts and local inspectors will be available to answer questions. Event takes place at the Agricultural Hall in West Tisbury. Space is limited; RSVP in advance at bees@mass.gov or 508-281-6784. Presented by the MV Agricultural Society. 
  • May 6th through May 8th - Pink & Green Weekend - Pink & Green Weekend is an annual celebration of spring and Mother’s Day on Martha’s Vineyard. Enjoy a weekend full of local activities and events - from our 5K fun run/walk to the Pink & Green Dog Show, as well as sipping, shopping and eating your way through town.
  • May 6th through May 8th - Spectrum Film Festival - The festival, which focuses on lesbian, gay, bisexual, transgender, queer, questioning and intersex people and their stories, is showing six films either online or in-person from May 6 through May 8.
  • Sunday, May 8th from 10:00 AM 1:00 PM - Mother's Day Brunch at Harbor View Hotel - Mother’s Day Brunch is a signature Edgartown spring experience. The culinary team has created an incredible menu in celebration of the moms we will be welcoming. Reservations strongly recommended, please call 508-627-3761. 
  • Saturday, May 7th at 10:30am to 11:30am - Mother's Day Blooms - Learn the art of floral design with Louise Sweet. Louise has over 30 years of experience designing stunning floral arrangements for the Vineyard's most beautiful weddings. Come and make a bouquet for a special mother or leave the kids at home and make one for yourself. Registration is required.
  • May 7th and May 14th from 2:00pm to 4:00pm - Open House with Artist Margot Datz
  • Saturday, May 7th at 7:00pm -MVYRADIO's 2nd Annual Night Out For Non-Profits -The Island community is invited to the P.A. Club in Oak Bluffs for the Second Annual MVYRADIO Night Out For Nonprofits. MVYRADIO is again holding a party to celebrate the organizations and the people who care for and support this community. The radio station will provide free food and live music so folks can dance the night away and interact with the people behind many of the important Island organizations who are doing good work on the Vineyard. Donations will be given as a grant to the MV Nonprofit Collaborative to fund scholarships for the certificate in nonprofit management and leadership from The Institute for Nonprofit Practice.
  • Sunday, May 8th at 1:00pm to 3:00pm - Mothers' Day Portraits - Photographer Lynn Christoffers will offer free portraits to all grandmothers, mothers, and families in honor of Mother’s Day. Lynn will take photos in the library’s Children’s Room and will send you a jpeg via email. Bring your own mother, or grandmother, or children, or whomever is special to you, to help celebrate Mother’s Day. (No pets, please). This event is free and open to the public. 
  • Friday, May 13th at 8:00pm - Artists for Climate Action at The Ritz -Join us at the Ritz for music, art, and Island footage from Martha's Vineyard Film Festival as we ring in the Friday evening of Climate Action Week. Music with: DCLA (Dukes County Love Affair), DJ Ricky Prime, and more TBA! Hosted by Vineyard Future Works. This is a Climate Action Week event.
  • Saturday, May 14th at 1:00pm to 2:30pm -Bird Bingo Safari - Prowl with a twist! Grab a bingo board and join the Trustees of Reservations to explore Cape Poge Wildlife Refuge via oversand vehicle. We will look out for our avian visitors and residents. Program starts at Mytoi Garden parking lot (approximately 2.8 miles drive/walk/bike from Chappy Point). Parking and bike racks are free at Mytoi Garden. 
  • Tuesday, May 17th at 4:30pm -Book Talk with Ben Shattuck & Jenny Slate - Join us at the West Tisbury Library for a book talk with author Ben Shattuck. Ben will read from his newly released book, Six Walks: In the Footsteps of Henry David Thoreau followed by a Q&A with Jenny Slate. Books will be available to purchase from Bunch of Grapes Bookstore. 
  • May18th through May 22nd - Martha's Vineyard Film Festival - Mark your calendars. The 22nd annual Martha’s Vineyard Film Festival will take place this May 18–22 at our new home at the Grange Hall in West Tisbury. We are looking forward to having you back on our couches, watching the best films from around the world.
  • Saturday, May 21st at 7:00pm to 2:00am - Fly Rod Striped Bass Catch & Release Tournament - This one-night team shore fly-fishing contest is built on fun and camaraderie. Everyone who joins and is present at the Sunday morning breakfast and awards ceremony held at the Rod and Gun club has an opportunity to win one of many great prizes generous supporters contribute each year. Team members must each fill a fish quota. Plaques are awarded in three categories: Roberto Germani Trophy to the team that reaches its fish quota with the earliest time; Arnold Spofford Trophy in which each member fishes with only one fly; Sonny and Joey Beaulieu Trophy for the largest striped bass released. Registration is from noon to 3 p.m. at the Rod & Gun Club.
  • Friday, May 27th from 3:00pm to 6:30pm - Grace Church Lobster Rolls -Grace Episcopal Church in Vineyard Haven will begin serving Lobster Rolls from 3 to 6:30 p.m. on Friday nights beginning Memorial Day Weekend, May 27. Friday Night Lobster Rolls at Grace Church will be available by ordering online through Grace Church’s website:  www.graceepiscopalmv.org or our app:  https://m.appbuild.io/adventca. Phone orders will be possible by calling 508-693-0332. Pickup will be at 34 Woodlawn avenue in Vineyard Haven on Fridays from 3 to 6:30 p.m. Our usual menu of lobster containers with two rolls on the side, chowder, hot dogs and an assortment of pies will be available. 
  • May 28th & 29th from 10:00am to 4:00pm - Vineyard Artisans Memorial Day Festival - The only art show on Martha’s Vineyard exclusively featuring all Island artisans with handmade fine furniture, sculpture, clothing, fine art one of a kind jewelry, fine ceramics and so much more.
  • Sunday, May 29th at 2:00pm to 10:00pm - Music On the Rock! - TPS Productions and DJ Cartel present The Itals, Exco Levi & The Naya Rockers, DCLA and more. Reggae, rock and dance music will fill the air on May 29th behind The Cove Minigolf in Vineyard Haven. Gates open at 2 p.m., with live music starting shortly after! Local acts Dukes County Love Affair, The Dock Dance Band, DB x N1D, and Reel Dubz Sound will support touring reggae music greats, The Itals and Exco Levi & The Naya Rockers. Do't miss this family friendly day of music, beer, food, kids' outdoor games and mini golf!