By Lauren Matison Photographs by Tony Cenicola

Original Article October 23, 2023

On the North Fork of Long Island, glasses are clinking to 50 years since a young couple planted the first commercial vines in the region. Today, with more than 40 North Fork vineyards producing award-winning merlots, sauvignon blancs, and cabernet francs, the 30-mile-long peninsula at the eastern end of the island, in New York, is also abuzz with new women-owned businesses: There are sustainable seafood restaurateurs, second-career farmers sharing their love of oysters and quahogs, innovative gallerists and pioneering winemakers finally uncorking dreams of their own. At any time of year, you can easily explore the area over a weekend. But in late fall, the crowds have ebbed, the beaches are mostly empty, locals are savoring the autumn harvest, and the crisp mornings feel ripe for an outdoor adventure along the timeless waterfront.

Recommendations

  • Borghese Vineyard & Winery looms large on the site of Long Island’s founding vineyard, providing generous wine flights and an art gallery.
  • Poppy & Rose is a new female-owned boutique winery with a patio on which to enjoy sauvignon blanc and apple cider doughnuts.
  • Glory provides tours of Peconic Bay on an electric-powered boat, offering local history, stunning scenery and a chance for kids to take the wheel.
Activities and museums
  • Inlet County Pond Park has a perfect short hike that begins at the North Fork Audubon center and ends at the beach.
  • Orient is a beautiful hamlet in which to ride a bike. Visit farm stands like Sep’s, eat crepes and dumplings at Opties and Dinghies and get spectacular views of Peconic Bay and Long Island Sound.
  • VEME Studios is on a mission to make art more accessible, offering drop-in classes for abstract art, candlestick-making, figure drawing and painting your own clothes.
  • Custer Institute and Observatory is Long Island’s largest astronomical observatory, where locals gather on Saturday nights to see celestial features like the rings around Saturn and craters on the moon.
  • Southold Indian Museum highlights the Native American narrative with a collection that includes ceramic pots, 11,000-year-old projectile points and wampum jewelry from the Fort Corchaug archaeological site.
  • East End Seaport Museum chronicles the region’s storied maritime history and runs a Saturday-evening cruise to the famous Long Beach Bar Lighthouse, known colloquially as Bug Light.
Restaurants and bars
  • Anker draws regulars with an inventive locavore menu and a European vibe, as does its next-door wine bar, Alpina.
  • Little Fish puts a new spin on classic seafood dishes in a vibrant space near the beach.
  • Minnow at the Galley Ho raises the bar on sustainable seafood and waterfront dining.
  • Brix & Rye slings creative cocktails with a speakeasy vibe, as well as delicious pies from the upstairs 1943 Pizza Bar.
  • Bruce & Son is a popular all-day brunch spot, serving killer egg sandwiches and great coffee from the North Fork Roasting Company.
  • Coffee Pot Cellars has a winning blend of good wine, sustainability initiatives and art.
  • Meadowlark is a new winery from Macari Vineyards that makes small-batch wines in a dreamy pastoral setting, and is home to popular Friday-night pizza parties.
  • Aldo’s is a Greenport coffee institution with a prime location near waterfront attractions like the antique carousel and a public camera obscura with 360-degree views.
  • Salumeria Sarto has become the new darling of Greenport’s Front Street eateries, serving specialty sandwiches, artisanal meats, cheeses and fabulous focaccia.
Shopping and galleries
  • Ray is an exquisitely curated shop with Matisse prints, Murano glass and retro-style North Fork travel posters designed by the owners Michael Aron and Nola Lopez.
  • Alex Ferrone Gallery shows striking photography, paintings and mixed-media works by artists from the region and beyond.
  • Willoughby is a new art salon that doubles as a refuge for artists and art lovers at the Vine + Sand bed-and-breakfast.
  • Nova Constellatio Gallery is an open studio packed with landscape art by the contemporary realist oil painter Isabelle Haran-Leonardi.
Where to stay
  • Zey Hotel is an artsy 10-room boutique hotel in Greenport with a garden, complimentary bikes and a continental breakfast. Doubles start from around $350.
  • Silver Sands Motel & Beach Bungalows breathes new life into an iconic 1950s property, featuring 20 design-conscious motel rooms, 15 beach shacks and bungalows, a restaurant and bar, complimentary bikes and 1,400 feet of secluded beach in Pipes Cove. Double rooms start from around $200.
  • A Walk in the Woods B&B offers charming accommodations and peaceful woodsy hiking trails just a five-minute drive from Cedar Beach in Southold. Doubles start from around $290.
  • For short-term rentals, options abound throughout the North Fork. Consider a guest cottage steps from the town of Southold, or one within walking distance to vineyards in Cutchogue.
Getting around
  • The North Fork is a mostly car-dependent region; Greenport, however, is a small, walkable town with a Long Island Rail Road station, and the Hampton Jitney bus makes 16 stops throughout the North Fork. The South Ferry (from $3) offers a short scenic ride across Peconic Bay to Shelter Island. Dan’s Bike Rental will deliver a hybrid bike, helmet, lock and basket anywhere from Mattituck to Orient. And if you can’t decide on a designated driver, Vineyard Vans is a reliable transportation company.

Itinerary

Friday

4 p.m. Cheers to women and wine history
On Route 25, one of two main roads brimming with vineyards, bucolic vistas and farm stands, look for the big red barn and sign for Poppy & Rose in Aquebogue. After more than 15 years as a winemaker for Bedell and Macari, Kelly Koch recently opened her own boutique winery, which shares a tasting room with Woodside Orchards. Sip bright, peachy varietals like the sauvignon blanc ($13) — or have a non-alcoholic apple cider ($4) — best enjoyed on the patio with a warm cider doughnut ($2). It’s tempting to try more pours and nibbles nearby, such as at Terra Vite and the Dimon Estate, both newcomers, or the 40-year-old Paumanok Vineyards, but history is calling on the North Road (Route 48). At Borghese Vineyard, recline on a blue Adirondack chair next to Long Island’s first commercial vines and raise a glass of sparkling rosé ($15) to Louisa and Alex Hargrave, who started a movement on this hallowed ground in 1973.

 
7 p.m. Dine above the waterfront
In Greenport, the top floor of Anker restaurant is a visual amuse-bouche with sweeping views of Peconic Bay, seen beneath a sunny, striped awning, and a glamorous crowd. A hyperlocal, lean-waste menu changes every month or so, and the chef Diego Garcia cooks from the quintessential North Fork farms playbook: goat cheese from Catapano, produce from the farms KK’s and Deep Roots, fish from North Fork Seafood and duck from the fifth-generation Crescent. Greenporters may opt for the latest communal offering, say a paella verde ($95, serves about three people), or dive into dependable dishes like mussels ($26) with Anker’s “mother sauce” (a slurp-worthy blend of sun-dried tomatoes, miso paste, capers, lemon and herbs), which pairs nicely with a crisp rosé pet-nat ($15) from Macari Vineyards.
 
 
 
9 p.m. Try the bartender’s choice
Brix & Rye, opened by Evan Bucholz nearly 10 years ago, is a treasured Greenport speakeasy. In an intimate, dimly lit space dating back to the 19th century, when Stirling Square was a horse stable, regulars come to learn as much as to imbibe. At the bar, after ordering a refreshing Northside Collins ($14) or a Sazerac ($12) — or better yet, the bartender’s choice — enjoy talking spirits and cocktail history with Mr. Bucholz as he carefully mixes your drink. He’ll even be happy to write down the recipe for you, which may involve category-defying spirits like Late Embers, a smoked sunchoke and honey spirit from the nearby Matchbook Distilling.

 

 

Saturday

9 a.m. Go for a seaside joy ride
Pedal the far East End, through East Marion’s historic district and into the hamlet of Orient, to immerse yourself in the romantic seaside that has long inspired creative minds: the poet Walt Whitman in the 1840s, members of the Peconic Art Colony, the artists Whitney Hubbard and Richard Serra, and today’s New York transplants like Agathe Snow, an artist and mushroom farmer in Mattituck. Rent a bicycle (Dan’s Bike Rental will deliver one to you, $30 for the day) and make the 10-mile round trip from Greenport to Latham Farmstand early in the morning, when the North Road is most peaceful. Riding the wide shoulder, you may catch a fisherman wading waist-deep for porgies and spot dedicated residents picking up litter at Truman’s Beach; pitch in by grabbing a trash bag and gloves at the welcome building in the beach parking lot.
 
 
 
10:30 a.m. Discover the gems of Greenport
It’s taken a village to preserve the character of Greenport, whose seaport district is listed on the National Register of Historic Places. Wary of commercial development, locals banded together to buy the beloved coffee hub Aldo’s and to save the Greenport Theater, now the North Fork Arts Center. The mom-and-pop-shop vibe is on full display on Front Street: Ray is a trove of art and décor mostly from the 1950s to 1980s, and at VEME Studios, try your hand at D.I.Y. tie-dye, watercolor and mug pottery. From noon, grab a $3 hunk of focaccia at Salumeria Sarto, a five-minute walk from the small yet substantial East End Seaport Museum. On Main Street, admire the work of the realist landscape painter Isabelle Haran-Leonardi at Nova Constellatio Gallery, along with Chris Hamilton’s nautical photographs at his weekend stall in front of Lydia’s Antiques.
 
1 p.m. Savor a sustainably minded feast
From Greenport, drive 20 minutes along scenic Route 25, arriving at the tip of New Suffolk to Minnow at the Galley Ho, perched between a community garden and Peconic Bay. Opened in the spring by the photographer and conservationist Andrea Tese, the restaurant serves line- and trap-caught fish and organic, seasonal produce. Follow the live acoustic music to a back patio overlooking the New Suffolk Waterfront and order the Mattituck mushroom bruschetta ($25), a platter of “can’t get more local than this” oysters from neighboring Peeko Oysters ($20 per half dozen) and spicy bigeye toro on crispy rice ($24). Too good to share, the fish tempura sandwich ($27) is served with a sweet homemade hot sauce, pickled radishes and cabbage slaw. (Ask for the sandwich with melted Gruyère, the way Ms. Tese eats it.)
 
 
 
2:30 p.m. Pair wine with art
A five-minute drive up the road from Minnow is Alex Ferrone Gallery, whose recent shows have featured photographs of Antarctic landscapes, a mixed-media celebration of trees and Ms. Ferrone’s own “Aerial Observations” photographic series. Around the corner, Meadowlark is a new, innovative small-production winery with a wild garden for sipping sauvignon blanc ($15) among picnickers and pollinators. Heading east, stop in at the quirky winery Coffee Pot Cellars, with its giant cork-studded brontosaurus, monarch butterfly mural and paintings by snails (yes, snails). Buy a bottle of merlot ($18), and Coffee Pot donates one milkweed plant to farmers to help sustain monarch butterflies. And Pamela Willoughby’s art salon has opened at the new boutique hotel Vine + Sand with otherworldly installations by the artist Randy Polumbo and photographs by Marcia Resnick.
 
6 p.m. Eat a seafood dinner, then watch the sunset on the sound
At Little Fish, a restaurant at the end of Kenney’s Road in Southold, locals come for the food and stay for the sunsets and live music. Beneath Pollock-esque paintings, created by the staff and displayed on the ceiling, diners sit in seafoam-green chairs draped with sheepskin, sharing spicy tuna tartare taquitos ($16), monkfish tikka masala ($38) and soba noodles with local razor and littleneck clams in a creamy, coconutty broth ($21). Little Fish has only been open since last spring, but plenty of locals have already adopted the routine of walking a block to Kenney’s Beach after dinner to clap at the sky’s colorful curtain call on Long Island Sound.
 
 
 
 
8 p.m. Stay up for a celestial spectacle
Custer Institute and Observatory, established in 1927, is the oldest and largest public astronomical observatory on Long Island. At the top of a winding staircase, in a 22-foot steel dome, look through a 10-inch Zerochromat refracting telescope, which is powerful enough to let you see the rings around Saturn, the bright clear craters of the moon or a globular cluster of several hundred thousand stars in the Hercules constellation. Before your visit, consult the Night Sky Planner and Custer’s calendar for special events like classical piano concerts and meteor-shower viewings. Across the street from the Southold Indian Museum, the observatory is only open to the public on Saturday nights, with a $5 suggested donation.

 

 

Sunday

9:30 a.m. Hike to a secret beach
While the rest of North Fork’s nature enthusiasts are at Laurel Lake Preserve, it’s likely you’ll have the 55-acre Inlet County Pond Park all to yourself. Less than two miles north of Greenport, the 1.3-mile hike begins at the North Fork Audubon nature center, which is aflutter with wildlife amid a native garden and grasslands restoration project on the North Fork Pollinator Pathway. On a meandering, well-marked trail through a mature oak forest and jungly terrain, use Cornell University’s Merlin Bird ID app to identify various bird calls, like those of the gray catbird or tufted titmouse. Pause at the pond viewing deck for the mute swans, swooping tree swallows and ospreys shrieking above Long Island Sound. After a short amble, you’ll reach a white sandy beach with royal blue water and a welcoming driftwood bench.
 
 
 
11 a.m. Eat a towering egg sandwich
In the same way Greenport locals go to Ellen’s on Front for fried duck wings, Maroni’s Southold for lobster bisque or Briermere Farms for fruit pies, they make a beeline for Bruce & Son’s egg sandwich ($17): a brioche bun that holds a holy combo of folded omelet, melted Gruyère, pickled onion, baby arugula, dijonnaise and candied bacon. Once known as Bruce’s Cheese Emporium, which was opened in 1974 by Bruce Bollman, the Main Street restaurant is now owned by his son, the chef Scott Bollman, who envisioned a rustic gathering place with an all-day brunch and strong community ties. Bruce & Son nurtures art partnerships with locals like the curator Jonathan Weiskopf of VSOP Projects, a contemporary art gallery, and the photographer Chris Hamilton, whose vivid sunsets hang on the wall.
 
 
 
12:30 p.m. Take a boat tour around Peconic Bay
On Peconic Bay, one of the Nature Conservancy’s “last great places” in the Western Hemisphere, join the captain David Berson aboard Glory, a 30-foot electric-powered harbor tour boat in operation since 1999. Sporting an old-school admiral yacht cap and a salt-and-pepper beard, Mr. Berson kicks off the 45-minute tour by blowing a giant conch shell. Gliding away from the harbor, Mr. Berson peers through yellow binoculars, pointing out notable boats and oyster farms. He mixes riveting history with not-too-salty jokes and secret local tips that alone are worth the $35 ticket. Near the end of the tour, you’ll arrive in Pipes Cove to find a beautiful beach and a protected wildlife habitat, with Mr. Berson smiling wide as if seeing it all for the first time.