Learn about the island’s pre-summer-resort history at the Martha’s Vineyard Museum ($6 off-season admission), which features a mix of oral accounts, art, costumes, and whale’s tooth carvings. The Vineyard-wide event series Plein Air Artist Sessions (various locations; free), organized by museum director David Nathans, is taking place throughout the month of October and will bring artists, poets, and musicians to points of interest like the Gay Head lighthouse and the museum's new campus to create art.
Explore Oak Bluffs’s concealed network of over 300 brightly painted “gingerbread” houses (miniature carpenter Gothic-style two-story structures), which started as a Methodist community in the 1830s and is known today as the Campground Cottages. With fewer crowds to face in the fall, it’s a good time to stroll through Trinity Park and peek through the windows to see the tiny living spaces inside.
Process your own turkey at the 200-acre FARM Institute, a fully operational farm and educational facility located just outside Edgartown, whose popular Chore Tours (9–11 a.m.; call ahead to schedule) offer hands-on work mucking stalls, gathering eggs, and building livestock fences. If manual labor isn’t your idea of a vacation activity, arrange a guided tour of the grounds or stop into the on-site shop for yarn, wool, meat, eggs, and seasonal vegetables.
You'll find the best variety of shops in Vineyard Haven rather than posh Edgartown or touristy Oak Bluffs. Stop by the iconic Bunch of Grapes Bookstore, which reopened in a new barnlike space this year and where you can find books by local authors. Across the street, the recently expanded Midnight Farm stocks unique finds like Indian-made Matta iridescent scarves ($218) and Relwen cowlneck sweaters for men ($296). Just a few doors down, Claudia Mainstreet offers a carefully edited collection of both classic and contemporary jewelry by local artisans as well as big name designers like David Yurman, Chan Luu, and Alexis Bittar.