Awesome Festivals and Events in Martha's Vineyard
A one-of-a-kind jewel within the “Outer Lands” archipelago of New England, Martha’s Vineyard has long been one of America’s legendary summer escapes—and, in fact, offers year-round appeal.
Our local partner here, Point B Realty, supplies the finest vacation accommodations on the island, fully up to the exceptional standards we adhere to at The 100 Collection. And the wonderfully varied Point B properties provide pitch-perfect springboards for experiencing any of the many annual festivals and other events in Martha’s Vineyard, a representative—if not exhaustive—sample we’re spotlighting below!
Grand Illumination (Oak Bluffs)
- August
On the third Wednesday in August, the Oak Bluffs “Campground”—the National Historic Landmark District of Wesleyan Grove—turns into a light spectacular with the annual Grand Illumination, the first of which took place way back in 1869 to honor the Massachusetts governor’s visit.
Following a Community Sing and Vineyard Haven Band music at the historic (1879) Tabernacle—part of a program presented by the Martha’s Vineyard Camp Meeting Association—the famed Oaks Bluff “gingerbread cottages” simultaneously fire up Japanese lanterns as darkness falls. Thousands attend this long-running event, one of signature summertime Martha’s Vineyard festivals.
Martha’s Vineyard Agricultural Fair & Livestock Show (West Tisbury)
- August
Held the third week of August, the Martha’s Vineyard Agricultural Fair & Livestock Show has been going strong since the 1850s, celebrating the island’s farming heritage and featuring an awful lot of timeless, family-friendly fun.
From livestock shows, pig races, and artwork to old-timey competitions such as the skillet toss, horse pull, and shucking, the “Ag Fair”—which goes down in West Tisbury’s venerable Agricultural Hall/Grange Hall—is the perfect way to celebrate the home stretch of summer on Martha’s Vineyard.
Martha’s Vineyard Food & Wine Festival (Edgartown)
- October
Presented through a partnership between the Vineyard Arts & Culture Foundation, Innovation Arts & Entertainment, and the marketing agency a21, the Martha’s Vineyard Food & Wine Festival celebrates the island’s foodshed and the terroirs of the Northeast more broadly in utterly delicious fashion.
Featuring everything from the bounty of the North Atlantic (lobster, oysters, etc.) to farm-fresh island produce, this culinary bonanza brings together a fabulous cadre of chefs, farmers, fishers, winemakers, and other artisans and fills its four days with Grand Tastings, multi-course dinners, cooking demonstrations, and much more spread across various Edgartown locations.
And it supports two very worthy causes: the farm-to-school initiatives of Island Grown Schools and the efforts of the Martha’s Vineyard Agricultural Society.
Martha’s Vineyard African American Film Festival (Oak Bluffs)
- August
This outstanding summer film festival celebrates cinema written, directed, produced, and otherwise made by people of color, as well as motion pictures placing people of color in central roles and storylines.
For better than two decades, Martha’s Vineyard African American Film Festival has brought leading cinematic voices and figures to the island while screening a huge variety of works, from shorts, comedies, and dramas to full-length documentaries. While the event taps multiple venues, the Martha’s Vineyard Performing Arts Center is a hub.
Martha’s Vineyard Book Festival/Martha’s Vineyard Author Series (Chilmark)
- August/summer
Launched in 2005 on the foundation of the Chilmark Community Center evening lecture series, the Martha’s Vineyard Book Festival draws authors from all across the country—and all across genres!
Readings, author talks, panel discussions, and book signings anchor this nationally renowned literary festival, which takes place on the Chilmark Community Center grounds.
It’s held every other year, with the 2012-established Martha’s Vineyard Author Series going down on the off-years on Thursday and Sunday nights during the summertime.
Vineyard Cup Regatta
- July
Part of the Classic Yacht Challenge Series, the Vineyard Cup Regatta benefits Sail Martha’s Vineyard while seeing some fleet and flashy buoy racing play out on the midsummer waters of Nantucket and Vineyard sounds.
Martha’s Vineyard Film Festival (West Tisbury)
- March
An off-season staple since 2001, the Martha’s Vineyard Film Festival presents a wide array of film screenings and related happenings anchored by a main venue of the Grange Hall. Past versions have featured such luminaries as Spike Lee, Amy Schumer, Ken Burns, and Bill Murray.
Outdoor Shakespeare (Tisbury)
- Summer
Get your Bard on during the summer courtesy of the Martha’s Vineyard Playhouse, which annually presents Shakespeare works at the Tisbury Amphitheater in Tisbury’s Vineyard Haven alongside original children’s plays. From Twelfth Night to The Tempest, from Romeo & Juliet to Much Ado About Nothing, immortal comedies and tragedies and tragicomedies come to life under the island’s friendly summer skies.
The Martha’s Vineyard Wind Festival (Oak Bluffs)
- September
The sea breeze struts its stuff front and center at the Martha’s Vineyard Wind Festival, the first edition of which blew into being in 1967 and ran for a couple of decades; the current version stems from a resurrection in 2011.
Held in Ocean Park in Oak Bluffs, the Wind Festival features both kite-making and kite-flying, with prizes in such categories as Largest and Smallest Flying Kite, Most Creative & Unusual Flying Object, and Best Wind Sculpture. There’s much else on tap, too, including model sailboat racing and DJ-supplied tunes.
The Vineyard Artisans Festivals (West Tisbury)
- Summer/fall/winter
Island-produced arts and crafts—from pottery, glassware, and jewelry to oil paintings, weaving, and mixed media—and their makers get the spotlight at the Vineyard Artisans Festivals, which include weekly summer juried art events as well as fall, Thanksgiving, and December holiday showcases. Venues include the Union Chapel, Agricultural Hall, and the Dr. Daniel Fisher House.
Martha’s Vineyard International Film Festival (Vineyard Haven)
- September
“Other Places, Other People”—that’s the guiding mission statement for the Martha’s Vineyard International Film Festival, established in 2006. Presented by the Martha’s Vineyard Film Society, which also manages a number of other annual film festivals, the MVIFF primarily (but not exclusively) features productions from outside the U.S., and along with the screenings themselves there are panels and other events, plus plenty of associated festivities around Vineyard Haven.
West Tisbury Farmers Market (West Tisbury)
- June – October
Experience the rich bounty of Martha’s Vineyard at the West Tisbury Farmers Market, originally started during the Great Depression and relaunched in 1974. Dozens of local vendors run stands at the market, which takes place at Agricultural (Grange) Hall.
Native Artisan Market & Festival (Aquinnah)
- July
Delve into Martha’s Vineyard’s Wampanoag heritage at the Native Artisan Market & Festival, where Indigenous makers showcase their wares at the Aquinnah Cultural Center each summer. Artist demos, hands-on crafts, and live music are additional draws to this long-standing showcase of Native artistry and culture.
Find the Perfect Getaway Spot on Martha’s Vineyard With The 100 Collection & Our Local Partner
Since 2008, Point B Realty, co-owned by Wendy Harman and Win Baker, has offered vacationers impeccable accommodations on Martha’s Vineyard: from coastal retreats to Colonial havens. Explore the entire collection of this trusted 100 Collection partner right here.
