A Weekend in Martha’s Vineyard

Located just south of Cape Cod, the triangular-shaped island of Martha’s Vineyard is undeniably one of the most exclusive summer hideaways in the U.S. For such a jet-set destination, however, it also maintains a reputation for friendliness. (Case in point: Strangers tend to wave at each other on the expansive beaches, something not often seen in such upscale enclaves.) 

These unique elements make the Vineyard an especially perfect destination for a summer such as this one. Good vibes and spacious outdoor landscapes abound, and the island boasts a soothing charm that feels a world away from the crowded bustle of the Northeast’s metropolitan cities.

Sunrise over Martha’s Vineyard. Photo courtesy Harbor View Hotel.

Just short of 100 square miles and encompassing a handful of welcoming towns, the Vineyard offers a variety of vastly different “scenes.” There’s the peerless allure of Edgartown, the quietude of the interior farmland, the gingerbread cottages of Oak Bluffs, and the remote, otherworldly coastal beauty of its western villages (chief among them is Aquinnah, aka Gay Head). Adding to its idyllic ambiance, iconic New England lighthouses dot many a spit of sand.

This peaceful summer paradise is easily accessible by Tradewind Aviation’s regularly scheduled shuttle flights, private shuttles, and charter flights. For those looking for a much-needed escape, here’s how to spend a weekend in Martha’s Vineyard. Each of the establishments we’ve highlighted is ready to safely welcome guests, ensuring your getaway is relaxing and stress-free — as any Vineyard weekend should be. 

FRIDAY 

Photo courtesy Harbor View Hotel on Martha’s Vineyard.

4 p.m. Check into Harbor View Hotel, which celebrates its 130th anniversary this year and recently underwent 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 abode. 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 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).

6:30 p.m. An Edgartown institution courtesy of Eli Levy and Jamie Zambrana, the Atlantic Fish & Chophouse is beloved for its USDA Prime steaks, whole branzino, and numerous lobster dishes, from the lobster arugula salad to the lobster ravioli with beurre blanc — and especially the crowd-pleasing black truffle lobster mac & cheese. Don’t leave without trying the decadent five-layer Valrhona chocolate cake or the French-style Nutella cheesecake. If you’re opting for take-out, enjoy it at nearby Lighthouse Beach at dusk.

SATURDAY

Edgartown Books on Martha’s Vineyard. Photo courtesy Quadri Okunga.

9 a.m. Massachusetts is blueberry country, so rise and shine and head down to Bettini, the Harbor View’s all-day restaurant, for blueberry buttermilk pancakes. After breakfast, stroll into town along North Water Street to admire the waterside homes festooned with globes of blue hydrangeas. It takes just 10 minutes to hit the town center, where you can browse contemporary art at Eisenhauer Gallery, casual wear at the iconic Black Dog, and women’s apparel and jewelry at Nell. Don’t miss the excellent indie bookstore, Edgartown Books, and be sure to grab some chocolate pecan fudge for later at Murdick’s, which has been using the same recipes since 1887.

Photo courtesy of The Black Dog in Edgartown, Martha’s Vineyard.

12 p.m. Pick out a beach cruiser at Martha’s Vineyard Bike Rentals, then if you’re up for an easy, hour-long bike ride, hop on and pedal to South Beach. The Vineyard is known for its well-paved bike paths, and the ride is flat and rural. After seeing the narrow strands of sand around Edgartown, you’ll find South Beach to be a shock: Accessible over grassy dunes, the Hamptons-like beach is long and wide, with golden sands.

Grab a drink and cool off at the hotel pool at Harbor View Hotel.

5 p.m. Cool off with a refreshing dip at the hotel pool, and order up a cocktail from the Roxy pool bar. (We recommend the refreshing One in a Melon, made with vodka, watermelon, and basil.) For dinner, walk over to the casual Seafood Shanty: The local oysters from Katama Bay, the tuna roll, and the lobster quesadilla are standouts.

SUNDAY

The clay cliffs of Aquinnah on Martha’s Vineyard. Photo courtesy: Harbor View Hotel.

10 a.m. Explore more of the island by car (hint: you can borrow a Mercedes from the hotel, one of its many stylish amenities). One of the more unusual spots is the Oak Bluffs Campgrounds, where hundreds of Victorian-era cottages show off their candy colors. Then head out to far-flung parts west, to Chilmark and the clay cliffs of Aquinnah, and keep your eyes peeled for the Chilmark General Store, where you can load up on a picnic brunch of kale salads, baguette sandwiches, fresh-baked banana bread, and cinnamon rolls. 

Victorian-era cottages show off their candy colors in Oak Bluffs, Martha’s Vineyard. Photo: MVCC.

Finally, drive to Tisbury at the northern tip of the Vineyard to admire the West Chop Lighthouse, which dates from 1891 and stands 45 feet tall. It’s a wonderfully fitting way to cap off a visit to one of the Northeast’s most classic communities. 

To learn more about Tradewind’s scheduled shuttle flights, private shuttles, and private charter flights to Martha’s Vineyard 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.Edgartown Books

Hamptons Harvest: A Spotlight on 3 Beloved Long Island Farms

From the garden to the tides, Long Island farmers are known for their produce and delicacies of incomparable quality — and their stories are as rich and unique as their bounties. A man who started out growing mushrooms in his garden, a farm family that goes back to the 1600s, a Wall Street software developer who harmonizes with nature instead of the keyboard… these are the farmers who are raising food and raising the stakes in one of the country’s most discerning culinary regions. And it’s all reachable via East Hampton Airport in Wainscott, accessible by a Tradewind charter flight. Try giving these a taste.   

Open Minded Organics 

Open Minded Organics founder David Falkowski recalls starting his business 18 years ago, humbly growing organic mushrooms in his backyard in Sag Harbor Village. Diversification came first with produce, flowers, herbs, baked goods, and quiches. Local chefs also seek out his heirloom and modern hybrid tomatoes, which are grown bio-dynamically and never refrigerated.  

Photo courtesy Open Minded Organics

“The terroir really comes through in our tomatoes,” he says. “We take an eater’s approach to growing food.” In the last few years, Falkowski has added extracts and herbal supplements to his lineup, such as echinacea and maitake mushrooms, and the farmer was also approved by New York State to grow and process hemp. In fact, the demand for his hemp and CBD items spurred him to open even earlier last year. “That’s what’s really driving things at the moment,” he explains.  

But back to the mushrooms, where it all began: Falkowski says what sets his product apart is variety and freshness. “They are picked and right up for sale, within minutes, at our farm stand in Bridgehampton,” he says. “That doesn’t happen at a grocery store.”

The OMO Apothecary in downtown Sag Harbor is open seven days a week from 10 a.m. to 5 p.m. and sells hemp and herbal extracts, as well as locally made gifts. The farm stand, which sells snacks, sundries, and produce, is open seven days a week from May to October. 

Milk Pail Fresh Market 

Photo courtesy Milk Pail Fresh Market

Another thing you’re unlikely to find at the grocery store: long legacies. Not many farmers, in the East End or otherwise, can lay claim to a history that dates back to the 17th century, but the Halsey family of Milk Pail Fresh Market, located in Water Mill, can. John and Evelyn Halsey, along with their daughters Amy and Jennifer, are the 11th and 12th generations, respectively, of family farmers.  

“It's an honor and a privilege to know we are following in such a long lineage of farming traditions,” Amy says. “We all have different approaches that complement the business and meet the demands of our vast clientele.  I'm not sure the ancestors anticipated such a diverse and complex way of life, but we enjoy the benefits and challenges of life as we know it today.”  

And the fruits of their labors are reward enough. Apples (from Pink Lady to Fuji) and flowers (from roses to amaryllis) form the basis of their business, but Milk Pail also carries local wines, candles, soaps, cheese boards, and children's toys. Finally, Amy provides lessons on farm culture: “It's the explaining and education to the current clientele that is so important — important not just for the instant satisfaction, but for the understanding of what it's going to take to sustain us.”

Photo courtesy Milk Pail Fresh Market

Milk Pail Fresh Market is open every day of the week except Tuesdays, and its hours are 9:30 a.m. to 5:30 p.m. Milk Pail’s farm stand on Mecox Road is open seasonally on Friday, Saturday, Sunday, and Monday from 10 a.m. to 6 p.m.

Widow’s Hole Oyster Company   

Long Island’s offerings come from the water as well as the land. When top Manhattan restaurants need to source oysters, they come to Mike Osinski and his Widow’s Hole Oyster Company in Greenport. Osinski’s second act — the Wall Street wizard sold his software company 19 years ago — keeps the exalted chefs at those restaurants happy by giving his treasured bivalve mollusks “the spa treatment.”  

As Osinski explains, the tides serve as masseur and culinary artist: “We use the tides to clean and sculpt the oysters,” he says. “The oysters are placed in baskets attached to lines rigged at high tide. The surface is closest to the sun and has the highest density of algae, which is what oysters eat.” When the tide drops, the oysters and the gear are exposed to sunlight and air, which cleans them of predators and sycophants. Then Osinski and his team attach floats to the baskets, so they roll over 180 degrees from low to high tides. “This,” he explains, “gently tumbles the oysters, which causes them to grow a deeper cup and a thicker shell.”  

The process results in a flavor and texture responsible for Osinski’s top dishes: oyster stew, oyster pot pie, and noodles with burned scallions and oysters.  

The biggest difference between software and oyster care? “The moon and the tides control our day, instead of the sun.”

Tour the oyster farm during your trip out East by contacting Osinski directly at mike@widowsholeoysters.com.

New York State no longer requires travelers coming from outside New York and its contiguous states to quarantine, but it recommends unvaccinated travelers voluntarily receive a COVID-19 test three to five days after arriving in the state and complete a non-mandated seven-day quarantine (10 days if not tested). Asymptomatic international travelers who show proof of a negative COVID test are not required to quarantine.

To learn more about Tradewind’s private charter flights to East Hampton, please visit our website. To receive a private charter quote, please complete our charter request form or contact our charter 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.

Featured photo: Milk Pail Market