Updated March 14, 2023.
Martha’s Vineyard and Nantucket in Massachusetts are undeniably two of the most exclusive summer hideaways in the U.S. But even as jet-set destinations, both places also maintain a reputation for friendliness and a welcoming atmosphere.
Photo credit Harbor View Hotel.
Spacious outdoor landscapes define Martha’s Vineyard and Nantucket, as does a charm that feels a world away from the bustle of the Northeast’s cities. Even so, each location also boasts a wide array of events and activities throughout the summer months. Additionally, both destinations are easily accessible by Tradewind Aviation’s regularly scheduled service flights, private scheduled service, and private service.
For those looking for a much-needed escape this summer, we’ve put together a full line-up in Martha’s Vineyard and Nantucket.
Martha’s Vineyard
Located just south of Cape Cod, Martha’s Vineyard has long been a top summer getaway spot. The largest island off Massachusetts’ coast boasts the classic East Coast architecture of gingerbread houses and stoic lighthouses, as well as abundant sandy beaches, chic boutiques, and a watery horizon dotted with dozens of sailboats on any given day.
Stay at Harbor View Hotel, which is fresh off a top-down renovation of its coastal-contemporary décor. Located less than half a mile from the center of Edgartown (a three-minute bike ride), Harbor View is the quintessential Vineyard place to stay. Amenities include an outdoor, heated seawater pool, as well as a new fitness center. At the hotel, the main inn is the center of the action, but families should also take note of the specialty accommodations, including the one- to three-bedroom Captain’s Cottages and the 2,270-square-foot Presidential Skyhouse (boasting four beds, five baths, and spectacular views).
Harbor View Hotel / Image courtesy Harbor View Hotel
When it comes to top dining spots around town, look no further than the Atlantic Fish & Chophouse, beloved for its USDA Angus, branzino, and numerous lobster dishes, from the lobster arugula salad to the crowd-pleasing black truffle lobster mac & cheese.
Summer Events in Martha’s Vineyard
Late June means just one thing in Martha’s Vineyard: Edgartown Race Weekend, one of the nation’s oldest distance races. The 2023 races will take place from June 15th to June 17th. A staple on the East Coast racing calendar, these highly competitive but also lighthearted races attract boats and teams of all sizes and calibers from around the world.
The bulk of summer events in the Vineyard land in July and August, starting with the annual 4th of July parade in downtown Edgartown and fireworks in the Edgartown harbor. While each of the Vineyard’s six main towns host their own distinct Fourth of July events, Edgartown stands out for its time-honored traditions. The day centers around a late-afternoon parade at 5pm, where onlookers watch as immaculate floats, classic cars, and marching bands make their way down Main Street. Arrive early to claim a spot in the historic town center, known for its white Greek Revival-style architecture.
Grand Illumination Night / Image courtesy Martha’s Vineyard
Dating back to 1869 and taking place every third Wednesday in August ever since, Grand Illumination Night is a magical evening during which thousands of colorful Japanese lanterns illuminate the Gingerbread Cottages and Tabernacle in Oak Bluffs. This year’s event, which also includes a community sing and live music, takes place August 16.
The following day, August 17, kicks off the traditional Agricultural Country Fair in West Tisbury. A four-day event, the fair features old-school competitions such as a corn shucking contest and a horse pull.
Nantucket
Nantucket, translated as “The Faraway Land” from the native Wampanoag language, is a small place with a big history. One of the major whaling ports in North America up until the 1880s now attracts visitors from around the globe.
Stay at Hotel Pippa, newly opened in 2018 and featuring chic mid-century modern style, contemporary sophistication, and curated artwork made by leading Nantucket artists. Located in Nantucket’s historic downtown district, the hotel’s expert staff have their fingers on the pulse of the top experiences.
Sushi at Nautilus / Photo by Georgie Morley
For the freshest seafood (and freshest takes on classic seafood dishes) head to The Nautilus. The tapas-focused restaurant offers a wide array of small plates ranging from yellowfin tuna lettuce wraps to grilled lamb chops. Savor New American dining at its finest at Òran Mór Bistro. The intimate eatery specializes in unique dining experiences, from handcrafted cocktails to the menu of fresh pastas.
Regatta / Photo by Louisa Gould
Summer Events in Nantucket
Returning for its 52nd year is the annual Figawi sailing race. The long-distance sailing regatta was born in 1972 out of the spirit of camaraderie and competition between sailors. The 2023 race will take place from May 26-29.
June and July are filled with celebrations of the arts and nature. The Nantucket Film Festival takes place this year from June 21–26. The annual festival will feature a well-rounded, expansive program of online screenings, drive-in screenings, and intimate garden screenings and conversations. (All in-person gatherings are being planned in compliance with local and state public safety guidelines.)
Come July, enjoy the back-to-back events of the Nantucket Garden Festival (July 11–13) and the Nantucket Comedy Festival (July 13–15). The celebration of floral beauty this year highlights the unique garden ecosystems on Nantucket. Get your belly laugh on at the comedy festival, which benefits Stand Up & Learn, a local comedy education program, and this year features three nights of top-notch talent as well as a kids’ night.
Regatta sailing during Nantucket Race Week / Photo by Louisa Gould
Immerse yourself in the world of sailing during Nantucket Race Week, taking place August 16–20. The five-day event is hosted by the Nantucket Yacht Club and Great Harbor Yacht Club to benefit Nantucket Community Sailing.
While it takes place after Labor Day, another event highly worth noting is The Nantucket Project. A gathering of spirited practitioners and bright thinkers, the annual four-day gathering includes live talks, music, experiences, and film. The Nantucket Project never falters on its promise that audience members will “come curious and leave inspired.”