09/17/2026
5 reasons to be on island this weekend 🏖️
Music, art, a farewell sail, street festival, and a new play. All before Sunday.
🤔 Thinking about making the Vineyard more than a weekend thing? DM me, let’s talk. 🏡
🎶 Live music takes over the island through Sunday. Songwriters Fest, Sept 17–20.
Matt Casey
🎪 Circuit Ave shuts down for the best street festival of the year. Sat, Sept 19, 10am–6pm.
Photo Credit 📸 Jonathan Fleischman Jonathan Fleischmann
🎨 Original work, island artists, Grange Hall. Fri–Sat, Sept 18–19. Proceeds and sales directly support the artists, Galaxy Gallery (supporting local arts), and Habitat for Humanity Marthas Vineyard
⛵ A Vineyard icon sails home one last time. Parade of Sail, dockside celebration, ship tours. Sept 18–20.
Photo cred 📸 Jeanna Petersen Shepard
🎭 New Theater at the Martha’s Vineyard Playhouse. Fri–Sat, Sept 18–19. Circuit Arts
Photo cred 📸 Jenny Graham