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508-693-7832

10 Things to Do in May on Martha's Vineyard


 As we enter May on Martha’s Vineyard, signs of summer are everywhere – from the return of our favorite lobster roll to opening day of the Vineyard’s very own baseball team. Here are the 10 island-only events that will remind you summer is just around the corner: 

  1. Partake in a Pop Up: Kick off May with a pop up event at Morrice Florists on Friday, May 4. The evening Cocktail Kick Off party celebrates Vineyard artisans and other award-winning American crafts people. 
  2. Dine on Shellfish: On Friday, May 4, the Chilmark Community Center will host its annual Shellfish Extravaganza. Don’t miss this event with music by Johnny Hoy and the Bluefish, silent auction as well as free raw bar and chowder.
  3. Get Decked out for the Derby: Saturday, May 5 marks the Kentucky Derby and the Harbor View Hotel is celebrating with a Derby Party complete with DJ, photo booth, hors d'oeuvres and prizes for the best outfit and hat.
  4. Try a Trout Tournament: The eagerly awaited annual Trout Fishing Tournament is taking place on Saturday, May 5. The event for the children of Martha’s Vineyard features trout fishing in Duarte’s Pond, plus breakfast under a tent by pond and prizes.
  5. Chill at a Chili Contest: Try more than 25 chilis from professionals and amateurs alike at the annual Big Chili Contest. The all-day event on Saturday, May 5 features a mariachi band and all you can eat chili at the Portuguese American Club.
  6. Hear Memories of Menemsha: Head to the Chilmark Community Center on Wednesday, May 9 for a Waterfront Talk, “Chilmark - The Sea Sustains Us.” The lecture by MVM research librarian Bow Van Riper will explain the rich history of the fishing port Menemsha.
  7. Celebrate Mom in Style: Celebrate spring and Mother’s Day in Edgartown at the annual Pink & Green Weekend, May 11 – 13. Events and activities include discounts at Edgartown stores, cocktails at Chesca’s, the Pink & Green Dog Show and Mother’s Day brunch at The Dunes.
  8. Indulge in Lobster: Friday, May 18 marks opening night for Grace Church lobster rolls. Get your first roll of the season and celebrate one of the first signs of summer. 
  9. Support Vineyard Artisans: On Memorial Day weekend (May 26-27), head to Grange Hall for the opening show of the season of the Vineyard Artisans Festival. Stroll work by island artists and grab a bite to eat at this island institution event.
  10. Attend Opening Day: Cheer on the island’s very own collegiate summer baseball team on opening day on Thursday, May 31. The MV Sharks will take on the North Shore Navigators at the Shark Tank on Edgartown-Vineyard Haven Road.