Top Summer Events on Nantucket and Martha’s Vineyard

Just as the populations of Nantucket and Martha’s Vineyard increase dramatically every summer, so too do the islands’ rosters of community events and celebrations. Indeed, the fact that the islands have such jam-packed calendars merited a spot on our list of “63 Reasons Why We Love the Cape and Islands” in May/June issue of Yankee.  For a taste of what’s on offer, here’s a dozen of our favorite Nantucket and Martha’s Vineyard events for 2019 in June, July, and August. For more, visit the events calendars of the Nantucket Chamber of Commerce and the Martha’s Vineyard Chamber of Commerce. 

Top Summer Events on Nantucket and Martha’s Vineyard

Nantucket Summer Events

Nantucket Book Festival June 13–16

Held at various venues across the island, this festival celebrates books and reading in the broadest sense while also calling out the rich literary traditions of Nantucket. Highlights include appearances by Susan Orlean, author of The Orchid Thief and The Library Book, and Nantucket’s own Nathaniel Philbrick (In the Heart of the Sea, Mayflower).

Nantucket Film Festival June 19–24

One of the premier destination film festivals in the world, the Nantucket Film Festival offers more than 100 film screenings alongside signature programs such as its annual Screenwriters Tribute. The 2019 schedule is still being set, but among the high points of previous years were appearances by Ben Stiller, Adam Driver, and Gabourey Sidibe, as well as an all-star comedy roundtable with the likes of Whitney Cummings and Kristen Schaal.

Nantucket Art & Artisan Show July 18–21

The creativity of more than 60 local and nationally recognized artisans and craftspeople takes center stage at this long-running fund-raiser for Small Friends on Nantucket, which helps provide the island’s youngest kids with top-quality quality early education and care. Join the weekend crowd in browsing fine pottery, glass, furniture, jewelry, folk art, textiles, antiques, and other covetable wares, or buy a pass to the opening-night preview party for first dibs.

Nantucket Atheneum Dance FestivalJuly 22–27

Drawing on star power from the New York City Ballet, Miami City Ballet, and Pacific Northwest Ballet, this festival includes free programs for all ages — films, classes, workshops, etc. — and culminates with two evening performances. All proceeds benefit the Nantucket Atheneum.

Boston Pops on Nantucket Aug. 10

Jetties Beach is the backdrop for this annual visit from the Boston Pops Esplanade Orchestra and conductor Keith Lockhart, whose program of crowd-pleasing tunes culminates in a spectacular fireworks display and a performance of the 1812 Overture accompanied by the ringing of island church bells.

Nantucket Race Week Aug. 10–18

Among the highlights of this sailing extravaganza — nine days of races, parties, and award ceremonies — are the Nantucket Regatta, part of the prestigious North American Panerai Classic Yachts Challenge Series; the IOD Celebrity Invitational; and the Opera House Cup, the oldest classic sailboat race on the East Coast, which draws a fleet of some 100 vintage yachts.

Martha’s Vineyard Summer Events

FILMUSIC Festival June 20–23

Martha’s Vineyard is known for its rich film-related offerings, and kicking off the island’s summer season is this popular hybrid festival of music and cinema. Live performances are interspersed with screenings of movies that have strong musical ties, such as last year’s Itzhak, a biopic about violinist Itzhak Perlman, and Hearts Beat Loud, about father-and-daughter musicians. It’s presented by the Martha’s Vineyard Film Society, which also hosts the Martha’s Vineyard Documentary Week in August; another August event to look for is the Martha’s Vineyard African American Film Festival.

Vineyard Cup Regatta July 12–14

More than 100 sailboats of all kinds — from schooners and catboats to modern racing yachts — grace the waters of Martha’s Vineyard for this annual 14th annual nautical showdown, which benefits the island’s community sailing program. The race courses have been designed to both test the competitors and provide a great view of the action from land. Bonus for sailing fans: A few weeks later comes the Edgartown Yacht Club Race Weekend and its historic ’Round-the-Island Race.

Martha’s Vineyard Book Festival Aug. 3–4

A biennial treat for book lovers, the Martha’s Vineyard Book Festival returns in 2019 with a roster of big-name guests: John Grisham, Richard Russo, 2018 National Book Award winner Sigrid Nunez, 2019 PEN Book of the Year Award winner Nana Kwame Adjei-Brenjah, and Mary Norris, copy editor for The New Yorker and author of Greek to Me: Adventures of the Comma Queen. Also of note: CNN’s Jim Acosta (The Enemy of the People) will address the challenges of journalism in the current political climate.

Grand Illumination Aug. 14

As evening falls, dozens of colorful Chinese and Japanese lanterns adorning the iconic gingerbread cottages of the historic Oak Bluffs Campground create a magical tableau of glowing lights. Dubbed the Grand Illumination, this lighting is preceded by a community sing and performance by the Vineyard Haven Band.

Martha’s Vineyard Livestock Show and Fair Aug. 15–18

Now in its 157th year, this West Tisbury–based fair is filled with old-time fun — shucking and fiddle contests, a skillet toss, horse pull, woodsmen competition — plus dog and livestock shows, arts and crafts, midway rides, and more.  

Vineyard Artisans Labor Day Weekend Festival Aug. 30–Sep. 1