By Mark Ellwood
The dramatic clay cliffs and windswept coastline of Martha’s Vineyard have drawn summer visitors for generations with its natural beauty and New England charm. Photo by Kelly MacLeod.
Forget the long-haul flight. America is home to some of the world’s most extraordinary escapes, and as we celebrate the country’s semiquincentennial, there’s no better time to revisit some of its most storied summer destinations: Martha’s Vineyard, Newport, and Kennebunkport. Here, we asked local tastemakers and insiders to reveal their favorite places, unforgettable experiences, and hidden gems for your next luxurious getaway.
NEWPORT, RHODE ISLAND
Newport became a playground for the wealthiest in the Gilded Age, as the Vanderbilts, the Astors, and more built summer cottages along Bellevue Avenue, and began throwing the splashiest bashes to celebrate the season. Summer here is still punctuated by a series of can’t-miss parties, says Trudy Coxe, who oversees The Preservation Society of Newport County, the nonprofit that manages 11 of the historic houses usually known as Newport Mansions.
The season starts earlier than ever, she says, driven in part by the younger summer visitors. “A lot of the older people like to stay in Florida until the latter part of June,” she says. The America 250 celebrations this year will turbocharge the calendar, she notes, including a repertory play season at Hunter House, the oldest home she oversees, which dates to 1748. Newport Divided, the play series that considers the American Revolution through the lens of several locals, including a Crown loyalist, will run from June 30 through August 29. Here, a few more of Coxe’s top recommendations.
Newport’s famed Cliff Walk traces its rugged shoreline, where sweeping Atlantic views unfold alongside legendary Gilded Age mansions.
- Newport Mansions Annual Ball
For the first time in more than a decade, the nonprofit’s annual August ball will be at Rosecliff, built by scoundrel-ish starchitect Stanford White and modeled after the Grand Trianon in Versailles. This year it’s a black-tie masquerade ball that will draw multiple generations to party together. Stick around until evening’s end, says Coxe, when the late Bob Hardwick’s namesake orchestra will pivot from big-band standards to pop. - Newport Mansions Chairman’s Dinner
“People sometimes give us $25,000 just to be invited to that party,” Coxe says of their highest-profile, most exclusive fundraiser, held each year in July. “It’s the crème de la crème.” - Lobster Bake, Bailey’s Beach
The private members’ club officially known as Spouting Rock Beach Association holds the unofficial end-of-summer party over Labor Day weekend. “Many families stay around to try to attend if they can,” says Coxe. It’s members-only, of course—but we know you’ll have the connections to score a ticket.
MARTHA’S VINEYARD, MASSACHUSETTS
Martha’s Vineyard has a deep maritime history and is world-renowned for its rich sailing culture.
Meg Nolan van Reesema, a travel specialist with Friend of a Friend Consulting, has been a lifelong visitor with an enviable black book of the best names to know. She shares some of her picks for the perfect summer.
The best party caterer? Buckley’s. Jessica Buckley started this firm two decades ago and it’s now run by her daughter Taylor. Nolan van Reesema says it’s known for “thinking out-of-the-box.” Ask them to include their signature prime rib on any menu.
Where to play tennis? Vineyard Family Tennis, which offers everything from starter programs for toddlers to college prep–level coaching. There’s pickleball too, of course.
The ultimate IYKYK, see-and-be-seen beach? Squibnocket (call it Squibby, like the locals do). “It offers the type of wave local surfers swear by due to the curve in the island, and the kind of privacy crowd-loathers seek.”
Classiest clam shack? Menemsha Galley. Don’t leave the island without scarfing some fresh swordfish or lobster rolls here. This clapboard classic is an almost–80-year-old local institution.
How to get there in style? Seastreak, which now shuttles from Manhattan to the Vineyard and has been a “gamechanger.” The full bar on board is a welcome bonus.
The hottest table? The Outermost Inn. Right on the island’s western tip in Aquinnah, so ideally placed for spectacular sundowners. “But it’s the entire evening trajectory,” says Nolan van Reesema, “cocktails on the lawn, followed by dinner on the patio supplied by their own herbal and vegetable garden,” that makes the journey worthwhile.
Buzziest new opening? The Wave. A team of Nantucket-based incomers has commandeered the onetime Garde East location for this new seasonal spot—and no wonder, she says, as it “has a coveted roof deck with water views.”
KENNEBUNKPORT, MAINE
New England–born Caroline Quinnis a travel specialist with Black Tomato whose longtime love affair with the area means she’s often recommending it to clients. “The beauty of Kennebunkport is that it’s stuck in time. You come here and feel it could be 1950 or 2026,” she says, “It forces you to slow down a bit.”
A traditional lobster bake at Kennebunkport’s White Barn Inn.
EAT Come here to gorge on lobster rolls with abandon. Take your pick between Nunan’s Lobster Hut on the east side or Mabel’s Lobster Claw, where the fishermen only have to walk across the street to deliver their fresh catch. Wash down a roll at Barnacle Billy’s in Ogunquit with its signature rum punch—be warned, it’s stronger than it seems at first sip.
DO Spend an evening at artsy Ogunquit, dipping in and out of the lively bars on Main Street, and idle away at Goose Rocks Beach, a three–mile–long spit of white sand north of the center that’s far quieter and more locals-heavy than the beaches closer to downtown.
STAY Cora is a houseboat launched by the Auberge-operated White Barn Inn, moored at its own dock and with a private roof deck. It was such a smashing success, the hotel’s adding a few more boats this summer.
ASK THE EXPERT Jenna Bush-Hager has been a lifelong Kennebunkport visitor, as her family has a sprawling estate here. Her three must-try spots? Earth, the restaurant at the five-star Hidden Pond resort. “It’s a family favorite in the piney woods.” The Clam Shack for a lobster roll is her go-to, and she also loves the Japanese restaurant, Rosalina. “I love that there is great sushi in Maine. Who would have guessed?!”
What to pack:
