This Part of Long Island Outshines the Hamptons in the Fall
Head to the East End’s lesser-known peninsula for wine tasting, vintage shopping, and more.
When you’d rather not take part in the bougie splendor of the Hamptons or feel as though you’ve outgrown the kitschy nostalgia of the Jersey Shore, look no further than the North Fork—a shabby chic stretch of Long Island that, in the last few years, has welcomed a bevy of new boutique hotels and restaurants run by Michelin-starred chefs. And unlike its resort-town counterparts, who tend to get sleepy once the chill arrives, the North Fork holds its own in the fall.
Long Island’s East End splits—like a fork—into two, with North Fork at the top and the Hamptons on the bottom. The northern peninsula boasts wineries, endless farm stands, and fewer crowds. It comprises a number of hamlets, with much of the action taking place in Cutchogue, Southold, Mattituck, and Greenport. While you can take the Long Island Railroad as far as Greenport, the North Fork is best experienced by car, because you’re going to want to make some roadside stops for apple cider donuts.
Now is an excellent time of year to spend a weekend, when you can have to yourself the peaceful landscapes that inspired artists like Walt Whitman and Richard Serra, taste what the fall harvest has to offer, and enjoy a glass of wine by a campfire. There’s a lot going on in town, too. On October 13, various oyster farms on the peninsula will spend the day shucking at the annual Greenport Oyster Festival, taking place at Little Ram. And right now you can make a pit stop on your way out from New York City to say hello to the Big Duck in Flanders.
Here are our recommendations for the best things to see, eat, and do in an autumnal “NOFO,” as the locals like to call it.
Travel Time:
2 hours from New York City
If You Only Do One Thing: Go Wine Tasting
The North Fork’s wine country has been compared to that of Napa, boasting more than 60 vineyards. The resulting product has an interesting terroir thanks to the growing region’s location between the Long Island Sound and Peconic Bay. Some of the most popular stops include Macari Vineyards in Mattituck, which has an elegant tasting room surrounded by the 500-acre vineyard, and Kontakosta Winery in Greenport, famous for its sweeping views of the Long Island Sound.
If you’re a fan of rosé, Croteux in Peconic is a must-visit, the only vineyard in the US exclusively dedicated to growing vinifera grapes. Meanwhile Sparkling Pointe is one of the few spots out east making bubbles—and they’ve been doing it well for 20 years. Over in Cutchogue, you’ve got McCall Wines, known for its Pinot Noir varieties, and Bedell Cellars, who have been specializing in Merlot since the ’80s.
EV&EM Vineyards in Laurel combines luxury with sustainability, as the first North Fork vineyard to earn certifications from both Long Island Sustainable Winegrowing and the New York Wine & Grape Foundation. Paumanok Vineyards in Aquebogue offers a laid-back experience, where you can sprawl out on an Adirondack chair and sip on the winery’s Chenin Blanc, a fan favorite. If you’re in Southold, make sure to stop by One Woman, owned by Claudia Purita, who brings her farming knowledge from Calabria, Italy.
Fill the Weekend With:
Outdoor Activities: While it might be too cold to take a dip, you can still enjoy a brisk walk along the pebbly shores of Orient Beach State Park, which overlooks Gardner Bay. Driving into the park is like entering a natural oasis; you might see an osprey or two soaring ahead as you pass by the red cedar, black-jack oak trees, and prickly-pear cacti that form its maritime forests. Sound View Dunes Park is another option, where you can take off on a hiking trail that offers both woodland forest and coastal dunes. If you prefer a lake surrounded by fall foliage, Laurel Lake Preserve offers 14 miles of hiking trails that give way to all kinds of wildlife, from snapping turtles and foxes to deer and otters.
Farm Visits: Apple season in North Fork starts in September, and there’s no shortage of pick-your-own orchards, from Breeze Hill Farm in Peconic to Woodside Orchards in Aquebogue (apple cider donuts are a given). If it’s a pumpkin-picking-corn-maze-hayride situation you’re after, check out Harbes Family Farm in Riverhead, or Lewin Farms in Calverton. And for the best pie in town, head to Briermere Farms; they’ve got all the seasonal varieties, from apple crisp to pumpkin.
Vintage Shopping: Shoppy-shops abound in Greenport, and you’re likely to walk past at least one vintage clothing or antique furniture store on your strolls through town. Walking into The Times Vintage is like stepping back in time to the ’70s, and you could spend hours scouring the technicolor racks. Nearby Lido sells globally-sourced homewares as well as a few one-of-a-kind vintage dresses. For antique furniture, Beal & Bell is a mid-century modern treasure trove. Over in Jamesport, sift through all kinds of reclaimed objects for the home or garden at the elevated junkyard that is Lumber & Salt.
Where to Eat and Drink on the North Fork
Breakfast: You can’t leave the North Fork without trying the famous breakfast sandwich at Greenport’s Bruce & Son, a perfect assemblage of folded eggs, gruyere, and sugared bacon. Southold General is a great place to stop by if you’re in need of some provisions to-go, while Love Lane Kitchen in Mattituck does a solid brunch. For coffee, stop by Aldo’s Coffee Company, a Greenport mainstay that has been handcrafting small-batch coffee since the ’80s.
Dinner: North Fork Table & Inn is a major name on the East End. The chef, John Fraser, also runs a few restaurants in New York City, such as Iris and La Marchande. Come here for classic farm-to-table dishes, like roasted Long Island duck and Georges Bank scallops. Minnow At the Galley Ho offers the very best in seafood, while Southhold Social excels when it comes to dessert (it’s helmed by pastry chef Francois Payard).
Drinks: Craft brewer Greenport Harbor Brewing Company boasts two locations in North Fork—one in Greenport and one in Peconic—and you can almost always expect fire pits and live music. Brix & Rye serves classic cocktails alongside some house favorites, like the popular Backsliding Presbyterian, a concoction of bourbon, Campari, ginger syrup, fresh lime juice, soda (they also make really good pizza).
Hotels on the North Fork
Budget: The Shorewood Inn in Jamesport—with its close proximity to Paumanok Vineyards and Jason’s Vineyard—is a simple, cozy choice if you’re looking to spend around $100 a night.
Splurge: Hotel Morraine is the best luxury option on the North Fork. The space has exactly what you picture when you think of coastal beach retreat: crispy, white linens; an expansive, heated pool; and a private beach. Originally advertised by a neon sign in 1957, Silver Sands has been re-imagined into an elevated, boutique motel, with quirky, colorful furnishings that hark back to its mid-century roots.
Our Pick: The Sound View in Greenport is another re-interpretation of an old-school motel, but we like it for its serene accommodations, on-site seafood restaurant The Halyard, and creative programming, such as a weekly Fireside Series.