A magical evening … Every August, residents of Wesleyan Grove, founded in the mid-19th century as a Methodist campground, hang colorful paper lanterns to celebrate Grand Illumination Night, a tradition that dates back to 1869.
Photo Credit : Nat Rea
Martha’s Vineyard has a well-deserved reputation as a summer getaway, but truth be told, there is plenty of fun to be had on New England’s second-largest island (behind only Mt. Desert Island) in any season. The year-round population of about 16,500 swells to more than 100,000 in the summer, so your experience will certainly be different depending on when you go. For the Weekends with Yankee episode “Adventurous Spirit” (season 4, episode 6), we helped celebrate the most highly anticipated event of the year on Martha’s Vineyard: Grand Illumination Night, when the iconic gingerbread cottages of Oak Bluffs are decked out with Chinese and Japanese lanterns. Planning your own visit? Here are a few of our favorite annual Martha’s Vineyard events. — Joe Bills
Best Martha’s Vineyard Events | Fairs, Festivals & More
Since its debut in 2017, the Spectrum Film Festival has been highlighting international films that provide a world perspective on LGBTQ+ stories and the people and issues behind them. In addition to the films, this annual event offers guest speakers, lectures and discussions, and other special events.
Part of the Bike MS series of races conducted across the country as a fundraiser for the National Multiple Sclerosis Society, Ride the Vineyard not only supports a great cause, it is also a unique way to experience the island’s wonders, whether you are riding in the 18-, 30- or 60-mile events, or if you are there to cheer on those who ride. All routes start and end at Martha’s Vineyard Regional High School in Oak Bluffs.
If the running doesn’t take your breath away, the scenery will at the annual Martha’s Vineyard Marathon and Half Marathon. From shaded bike paths to open fields and shoreline views, few courses can compare to this trek through the gently rolling hillside.
Presented as a collaboration between the Martha’s Vineyard Film Society and the Vineyard Conservation Society, the MV Environmental Film Festival showcases environmental films, hosts discussions about them, and even includes an exhibit of artwork by local student artists.
Kicking off on Memorial Day weekend and running twice weekly throughout the summer (with special shows at Labor Day, Columbus Day, Thanksgiving, and Christmas), the Vineyard Artisans Festivals are juried shows featuring works by many of the island’s most creative and skilled craftspeople, along with demonstrations of how they work. Held at the Grange Hall in West Tisbury.
Started as a small potluck in 1986, the Taste of the Vineyard gourmet stroll has evolved into one of Martha’s Vineyard’s most anticipated annual events. Participation is on the pricy side, but in return for that investment, you’ll sample great wines and food while supporting the Vineyard Trust, an organization whose mission is to preserve the island’s historical landmarks. The voyage starts on Main Street in Edgartown.
The annual Harbor Festival in Oak Bluffs is a one-day event that captures all the charm of a small-town festival, but in the beautiful surrounds of the town’s harbor. With live music, seafood, crafts, costumed performers, and antique car parade and even a Midsummer Faerie Festival.
A full weekend of racing, socializing and dining, the Vineyard Cup Regatta features a series of buoy races in the waters of Nantucket Sound and Vineyard Sound. Cheer on your favorites and make sure to pick up a Vineyard Cup bracelet, so you don’t miss out on the after-party. Proceeds benefit Sail Martha’s Vineyard.
The Grand Illumination of the Oak Bluffs Campground, better known as Illumination Night, sees the iconic gingerbread cottages of Oak Bluffs decked out with Chinese and Japanese lanterns. The tradition dates back to 1869, when it was first held to celebrate a visit from the governor of Massachusetts. As the sun goes down, the lanterns spark to life, accompanied by a community sing-along and a performance by the Vineyard Haven Band.
The Agricultural Hall in West Tisbury hosts one of the island’s longest-running and most anticipated yearly events. Since 1862, this now-four-day event has been a staple of Island summers. Today’s Fair features livestock competitions, rides, games, shucking and fiddle competitions, music, craft shows and demonstrations, pig races, food, an art show and more.
Every second year, Chilmark and Edgartown host readings, discussions and book signings featuring bestselling and prize-winning authors for the two-day Martha’s Vineyard Book Festival. Among the participants in recent years have been household names like John Grisham and Ann Patchett, Pulitzer Prize winners Richard Russo and Stephen Kurkjian, and James Beard award-winning food writers like Ruth Reichl and Kwame Onwuachi.
Watch features, documentaries and short films, meet filmmakers and actors like Spike Lee, Jodi Gomes, and Michael B. Jordan, and discuss the challenges being faced and the stories being told by independent African-American filmmakers during this week-long event.
Held at Union Chapel in Oak Bluffs, Built on Stilts is a community dance festival that offers up a different show on each evening of its four-day run. Celebrate the language of movement with local participants as well as representatives of some of the country’s most well-known and accomplished dance companies.
The Martha’s Vineyard Fil Society created its Documentary Film Week to celebrate the increasingly large role documentaries play in informing our public dialogue and shaping opinion. Five nights of showings, with filmmaker presentations and discussions galore.
Presenting a selection of films from around the globe, the International Film Festival presents many of the best movies making the rounds at Sundance and Cannes and the like, pairing them with discussions with filmmakers, politicians, artists and others who can speak to the issues being explored. The Festival’s juried short film competition is always a highlight.
Few events speak more directly to old-fashioned summer fun than the Vineyard’s annual Wind Festival, a free competition for kids and adults in friendly kite-making and kite-flying competitions, with awards given in categories like “best wind sculpture” and “highest flying.”
Running from mid-September through mid-October, the island’s biggest annual fishing derby has been attracting sportspeople to Edgartown since just after World War II. The event attracts serious competitors from around the world, but also plenty of amateurs looking to enjoy some of the world’s most beautiful sunrises and sunsets while fishing for their next great story about the one who got away.
A four-day feast celebrating the best culinary talent the island has to offer, as well as the fishermen, farmers, and artisans they rely on. Held the weekend after Columbus Day, the festival’s pairing of visiting guest chefs and vintners with local stars always makes for a unique, and delicious, experience.
This weekend-long holiday happening raises more than $50,000 for charity each year, drawing huge crowds for Santa’s arrival, the Teddy Bear Trot, the Christmas parade down Main Street, special sales and great deals in many shops, and the annual illumination of the Edgartown lighthouse. Four days of family-friendly events and fun.