We've barely reached cruising altitude when a flight attendant announces we've begun our descent into Martha's Vineyard, a small island off the coast of Massachusetts. In one hour—roughly the same time it takes to leave Manhattan in peak rush-hour traffic—we've touched down on the tarmac and walked through the quaint pitched-roof, flag-clad airport, a far cry from the bustle of New York City.
"Whenever I arrive here, I feel like I can breathe again," says Julia Wetherell-LeClair, co-founder of luxury fashion destination Orchard Mile, who has been coming to Martha's Vineyard for over 30 years. "There is a sense of relaxation that I don't experience anywhere else." There's truth to that sentiment—from the moment we arrive in Edgartown, the island's first colonial settlement, the pace slows. Row upon row of shingled houses stand tall, hydrangea petals blanket the streets like confetti, and the sea breeze carries the scent of salt from the Atlantic.
"I always feel like I need to go on vacation after going to the Hamptons, [but] the Vineyard is a lot more laid-back. I feel like I can actually check out," she explains. "Also, there are no chains, traffic lights, or parking meters on the island, which I think is very cool." The no-chain-store rule has kept major retailers away from Martha's Vineyard, but it's also meant that residents and vacationers have limited access to high-fashion brands.
Though Orchard Mile is a digital destination, it seemed fitting that Wetherell-LeClair would bring a retail pop-up to the place she feels most at home. "The Orchard Mile pop-up is essentially my 'mile.' It’s a mix of my favorite brands and [is] definitely a reflection of my personal style. I selected items based on all the things I do here during the summer," she says.
If you haven't made it to Martha's Vineyard this summer, there's still time. Ahead of Labor Day, Wetherell-LeClair shares the insider spots to eat, drink, and swim to explore this East Coast gem like a true local.
Best Paddleboarding Spot: You don't have to know how to surf or sail to make the most of Martha's Vineyard's picturesque coves and beaches. Wetherell-LeClair recommends stand-up paddleboarding in Squibnocket Pond or Edgartown Harbor if you're staying in town. "It's also fun to take a paddleboard across the harbor to South Beach. It's quite the workout and no easy feat but totally worth it," she says.
Best Vantage Point to Watch Sunset: Don't miss sunset while you're staying on the island. "Squibnocket has some of the best sunsets I've ever seen," she says, noting that Menemsha also a fierce contender. "Grab a warm buttered lobster roll from Larsen's Fish Market two doors down and take a picnic to the beach with some wine to sip while you watch. People come from all over the island for the countdown."
Best Street to Spot Your Dream Home: There's no shortage of quaint New England homes here. "The architecture all over the island is really beautiful and all slightly different depending on where you are," she explains. "However, North Water Street in Edgartown has some of the best quintessential New England homes. I love the old whaling captains' homes along the harbor."
Best Restaurant for Dinner: Planning a special meal during your stay? You can't look past L'Etoile, a chef-owned and operated restaurant in a historic whaling captain's house that serves light, seasonally driven fare. Her favorite? "The étuvée of Menemsha Lobster," says Wetherell-LeClair. "Also, you have to sit outside in the garden; it's so magical."
Best Rainy Day Activity: Though Martha's Vineyard boasts slightly better weather than neighboring Nantucket, it's best to plan for misty, overcast days on occasion. Reach out to Krishana Collins of Tea Lane Farm to schedule a flower-arranging class with family and friends. Alternatively, find her at the West Tisbury Farmers' Market on Wednesdays and Saturdays.
Best Cocktail Bar: There's no competition: "Covington. They make deliciously refreshing cocktails with fresh ingredients," she says. "My go-to is the Katama in the Afternoon. It's tequila with fresh strawberry, lemon, basil, wild myrtle and chili salt."
Best One-Stop Shop: Wetherell-LeClair curated the Orchard Mile pop-up so it has all the items you'd need while vacationing on Martha's Vineyard. "Whether you're looking for the perfect bathing suit and coverup for the beach, something casual for the farmer's market, or the perfect dress for a clambake, there's something at the pop-up," she says. Standout brands include La Double J, Temperley London, and Cynthia Rowley.
Best Activities for Kids: "I love how my life has now changed with Chloe because it has allowed me to do more things I normally wouldn't do," says Wetherell-LeClair of life with her 6-month-old daughter. "There are so many beautiful farms on the island that are fun to take her to. I also recommend Oaks Bluff for families. There's the famous Flying Horses Carousel, which kids love. You ride around collecting rings, and if you get the golden ring, you win!"
Best Coffee: Start your day right with Martha's Vineyard's best cup of joe. "Behind the Bookstore in Edgartown has the best coffee," she says. "They create these genius mixes like their iced mint latte, which is made with fresh mint leaves, or their hot lavender latte, which has fresh lavender sprinkled in."
Best Place for a Celebrity Sighting: Given the Obama family is currently vacationing on the Vineyard, we couldn't help but ask her where to spot an ex-president or celebrity. Surprisingly, her recommendation is a low-key spot to the island's southwest. "At the Chilmark General Store, you'll usually catch a celeb sitting in the rocking chairs on the porch with a slice of pizza or one of its amazing sandwiches."
Best Under-the-Radar Beach: Though Martha's Vineyard is small, it is possible to escape the crowds. Wetherell-LeClair recommends Lucy Vincent, a favorite local beach. "[It's] so under the radar that if you continue to walk farther down the beach it turns into a nude beach!"
Best Non-Beach Activity: Need a day away from the sun? "Take a drive up-island and check out the beautiful farms along the way, stopping at Vineyard Glassworks (it's like the Simon Pearce of MV) and Mermaid Farm; then end up at the famous clay cliffs in Aquinnah. They're breathtakingly beautiful and dramatic."
Best Bar to Dance the Night Away: The island might be quiet and quaint, but there are a few gems to visit if you're craving a livelier crowd at night. Try Atlantic or The Port Hunter. "They both have live music on the weekends, but Atlantic is more of a dance scene, and Port Hunter usually attracts a chill crowd with bands like Johnny Hoy and the Bluefish," she says. No doubt, there's more to this New England island than first meets the eye.