The East Coast oases of 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 Hotele
Spacious outdoor landscapes and a relaxing atmosphere define Martha's Vineyard and Nantucket, as does a soothing charm that feels a world away from the crowded bustle of the Northeast’s metropolitan 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 shuttle flights, private shuttles, and private charters.
For those looking for a much-needed escape this summer, we've put together a full line-up of events in Martha's Vineyard and Nantucket, as well as our favorite places to stay and eat.
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.
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.
Late July means just one thing in Martha's Vineyard: Edgartown Race Weekend, one of the nation's oldest distance races. The main event is the Martha's Vineyard Round the Island race, taking place July 24, but the events kick off July 22 with two days of Round the Buoys races. 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.
Grand Illumination Night / Image courtesy Martha’s Vineyard
Dating back to 1869 and taking place every third Wednesday in August ever since (save for last year due to the pandemic), 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 Wednesday, August 18.
The following day, August 19, 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, a horse pull, skillet toss, and livestock shows. On Friday night, August 20, lay back and enjoy the show of fireworks lighting up the sky.
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, it now attracts visitors from around the globe drawn in by its natural beauty, festivals, restaurants, and overall sense of serenity.
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. Centrally located in Nantucket's historic downtown district mere blocks from the harbor, the hotel's expert staff have their fingers on the pulse of the top restaurants, excursion opportunities, experiences, and anything else you might be seeking.
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, each designed to share with the table and pair with the larger plates of wagyu steak, Thai BBQ chicken, and blue crab fried rice. Savor New American dining at its finest at Òran Mór Bistro. Located up a flight of copper stairs in a historic Nantucket home, the intimate eatery specializes in truly unique dining experiences, from handcrafted cocktails using local spirits to the menu of fresh pastas, locally sourced meat and fish, and decadent small plates (think foie gras torchon and Spanish octopus paired with pork belly).
Regatta / Photo by Louisa Gould
Returning for its 50th 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 and today is a favorite local tradition. To celebrate its 50th year, the event has decided to expand from one to two days for the first time ever, covering both Saturday, May 29, and Sunday, May 30.
June and July are filled with celebrations of the arts and nature. The Nantucket Film Festival takes place this year from June 17–28—the first time in its 26 years that it will span 11 days. 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 13–15) and the Nantucket Comedy Festival (July 15–17). Postponed in 2020, the celebration of floral beauty this year returns for its 12th year in 2021 and highlights the unique and beautiful garden ecosystems on Nantucket, with an emphasis on sustainability, conservation, and gardening ethics for the long-term health of the island. 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 14–22. The nine-day event includes a bevvy of regattas, parties, and awards ceremonies, all hosted by the Nantucket Yacht Club and Great Harbor Yacht Club to benefit Nantucket Community Sailing, which supports youth sailing for local children.
While it takes place after Labor Day, another event highly worth noting is The Nantucket Project, happening September 23–26. A gathering of spirited practitioners and bright thinkers, the annual four-day gathering includes live talks, music, experiences, and film. Celebrating its 10th anniversary this year, The Nantucket Project never falters in making good on its promise that audience members will "come curious and leave inspired."
To learn more about Tradewind’s scheduled shuttle flights, private shuttles, and private charter flights to Martha’s Vineyard and Nantucket and booking your vacation, please visit our website. To receive a private charter quote, please complete our charter request form or contact our specialists at charter@flytradewind.com or 1-800-376-7922. To learn more about Tradewind’s comprehensive safety plan, please visit our COVID-19 Response page. For the latest travel updates, please visit our Travel Advisory page.