Explore the North Fork by sea and land

It’s 7 a.m. on a crisp October morning on the North Fork of Long Island and Stefanie Bassett is out in the middle of Gardiner’s Bay on a wooden boat, wearing bright orange waders and sampling oysters. It’s a far cry from two years ago when she was sitting in a boardroom in a slick Manhattan advertising office, wondering what she was doing with her life. “It was a constant hustle and I had to put on blinders and close myself off to the creativity that drew me to New York City in the first place, just to get through the day,” says Bassett. “I knew it was time to change something.”

So she and her wife, Elizabeth Peeples, an interior designer, uprooted everything and moved to the east end to reinvent themselves as badass oyster farmers and start Little Ram Oyster Company. Part of the draw was the North Fork itself: “We’re surrounded by water and farms and a lot of like-minded people,” says the 5’3” Bassett, whose outward appearance isn’t what you’d associate with a typical oyster farmer. “From the minute we moved out here, my creativity immediately came back.”

Not far away, Maria Rivero González — another new arrival who comes from a long line of Mexican wine producers — is checking the grapes to see if they are ready for harvest at RGNY, the sustainable vineyard she opened a year ago on the outskirts of Riverhead. González was initially attracted to the quality of the climate and the soil but grew to love the North Fork’s way of life. “It’s all about good food, good wine, and an easy vibe that brings you back to the basics,” she says.

The appeal of the North Fork that Stefanie and Maria describe has rung true with me and my husband for many years. Driven by the innovative energy embodied in the organic farms, biodynamic wineries, and boutique hotels, we escape to this bucolic 30-mile stretch of land any chance we get. We also appreciate the unpretentious authenticity that's been preserved by the locals for generations.

For this weekend's getaway, come along for a ride as we dive into the creativity of the North Fork's land and sea offerings. Who knows? Maybe you’ll visit for a weekend and stay a little longer than you might have originally planned.

-Laura Begley Bloom, New York's Senior WeekEnder Writer

Whether you want to soak in the sea air or experience farm life, these are the North Fork hotels on my shortlist:

For Instagrammers: Sound View on the outskirts of Greenport - Motor lodge with jaw-dropping water views transformed by a Brooklyn-based design team.

For Your Mixology Cravings: Lin Beach House in Greenport - Renovated Victorian guest house affiliated with Matchbook Distilling Co.; downstairs is Days Like These, the distillery’s craft cocktail bar.

For Surfer Wannabes: Greenporter in Greenport - Hang-ten at this affordable motel with fresh surf vibes. (We're rolling our eyes at ourselves here, too.)

For a Cheap Sleep: Hyatt Place East End in Riverhead - Hotel with plenty of style. Added plus: It’s attached to the aquarium and has access to the marina and kayaking.

For Wine Lovers: Shinn Estate Vineyards & Farmhouse in Mattituck - Four-room farmhouse inn set on an acclaimed vineyard. Wine tastings and tours included.

For Sweethearts: Sannino Vineyards Bed & Breakfast in Cutchogue - It's Tuscany in Cutchogue. Yes, you heard me right — a tasteful two-room vineyard that has views for days.

The floorboards creak as you walk through Preston’s Chandlery, a wharf-side boating-supply store in the village of Greenport. It hasn’t changed much since its founder, a Boston boat captain, came here on vacation in the 1800s and decided to stay. (Sound familiar?)

The North Fork’s marine heritage runs deep. Back in the 1700s, the village of Greenport was one of the most important whaling centers on the Eastern Seaboard; in the 1800s, commercial fishing, oystering, and shipbuilding took over. These days, recreational fishing is still big in these waters, which teem with striped bass and fluke, porgies and bluefish. Oystering is also making a comeback, thanks to a new generation farming these waters alongside crusty old baymen who have been here forever.

Want to embrace the life aquatic? Here’s how:

Charter a boat through North Fork Captains and go out for a day of fishing on what David Abatelli, vice chair of the East End Seaport Museum and a defacto local historian, refers to as a six-pack: “It’s short for six friends with a six-pack of beer — which is pretty much what you do if you're not catching any fish.”

Learn how oysters are cultivated with a tour at Widow’s Hole Oyster Farm, run by Mike Osinski, who ditched software to become an oyster farmer.

Stop by one of the little roadside oyster stands that line the North Fork, selling burlap bags filled with bivalves. Besides Little Ram, I’m a big fan of Southold’s Founders Oysters, started by a former ABC News producer.

Taste the terroir at Greenport’s Little Creek Oyster Farm & Market, whose motto is “Shuck Yourself.” Set in an old tackle shop with a firepit out front, the hipster seafood shack showcases local oysters and will teach you the fine art of shucking.

Spend the night at Greenport’s Menhaden, an impeccably designed black-and-white boutique hotel that’s named after a local fish. The staff can arrange bespoke fishing trips and cook your catch.

They're simple structures, but they're all unique in their own way. Lighthouses. If you're a fan like me, you're in luck — the North Fork, specifically Southold, has more lighthouses per capita than any other township in the United States.

If you start at the very end of the North Fork on Orient Beach, on a clear day you can spot five lighthouses, including Long Beach Bar, also known as Bug Light. (Spoiler alert, it looks like a water bug at high tide.)

Since it's getting to be that spooky time, I spoke with a local named Bob Allen, whose great-grandfather was a lighthouse keeper at Bug Light, to get the story on some of the more supernatural occurrences at some of the local lighthouses.

According to Allen, Race Rock Lighthouse, which you can see in the distance from Orient Beach, has been known to have whisperings of shipwrecked captains. And then there’s Plum Island Lighthouse: It’s haunted by Colonel Thomas Gardiner, a Revolutionary War hero. (If you visit, give him a salute from us.) Southold’s Horton Point Lighthouse is another spooky spot with a history of ghost sightings. And Allen has even lent a hand to ghost hunters at his great-grandfather’s lighthouse. “Years ago, I got a call from a paranormal investigator who wanted someone with a connection to Long Beach Bar to see if the lighthouse was haunted,” says Allen. “We discovered a ghost dog.”

▶️Want to feel like you’re on the beach in Greenport? Video: One minute at 67 Steps Beach

Hungry to taste the best seafood on the North Fork? Here’s a quick eats cheat sheet:

Breakfast: Main Road Biscuit Co. in Jamesport - Go for the North Fork Oyster Fry with local farm eggs, grits, and more. Breakfast served all day.

Lunch: Noah’s in Greenport - Sun-drenched space on the main drag run by a husband-wife team. Must order: the hot lobster roll on a locally made brioche.

Seafood Shack: Claudio’s in Greenport - A dockside dining spot with clams however you like them (and other classic seafood bites). Founded by a fisherman in 1870.

Pub Grub: Greenport Harbor Brewery in Peconic - Microbrewery with a modern American restaurant and beer garden (the original location is next to the old jail in Greenport).

Elevated Hotel Dining: The Halyard on the outskirts of Greenport - Waterfront restaurant at the Sound View with locally sourced fish dishes from Mattituck-born chef Stephan Bogardus.

Date Night: Frisky Oyster in Greenport - The name alone will put you in the mood at this elegant downtown bistro with sea-to-table dishes.

You could say that Claudia Fleming arrived in the right place at the right time. After making a name for herself in the New York food world at spots like Gramercy Tavern, the award-winning chef co-founded the North Fork Table & Inn back in 2006. It sounds almost pedestrian now, but at the time, the restaurant broke boundaries by featuring organic ingredients from local farms. “The North Fork was known for fried food — no one was trying to do upscale dining,” says Fleming.

At that same time, a new generation of farmers started populating the North Fork, buying land to do organic, natural farming and finding their place in the food chain next to the area’s many family-run farms, like Wickham’s, which has been in business since 1661. “The stars aligned,” says Fleming. “We all found each other and thrived off each other. A high tide raises all boats.”

These days, Fleming is working on a new dessert cookbook for home chefs and spends her free time paddleboarding on the North Fork’s placid bay waters, followed by afternoons of farmstand-hopping. We tapped into Fleming to get her expert go-to list.

Krupski Farms in Peconic – A six-generation farm with hayrides, a corn maze, haunted barn, and “the best white corn,” says Fleming. “They don't even open until their corn is harvested, then they go right into Thanksgiving with pumpkins and squash.”

Treiber Farms in Peconic – The sustainable farmstand sells farm boxes, honey, pesto, and all shades of veggies. “He's experimenting with a lot of produce, like nice greens and peppers,” says Fleming.

Sang Lee Farms in Peconic – In non-COVID times, there are tours and tastings; right now the farmstand stocks fresh flowers and produce. “They were the pioneers in organic farming on the North Fork and they have so much interesting Asian produce,” says Fleming.

Oysterponds Farm in Orient – “The best berries I have had other than the Santa Monica farmer's market,” says Fleming. “They're incomparable.”

Deep Roots + Farm In Southold – Pasture-raised pigs, chicken, and eggs, alongside flowers and vegetables. “It’s self-serve, so you can go at eight at night,” says Fleming. “When I was recently there, the variety of peppers was off the charts.”

Briermere Farms in Riverhead – “People swear by their homemade pies,” says Fleming.

Lavender by the Bay in East Marion – Locally produced lavender products. And when the lavender farm is in bloom in June, July, and September “it is not to be believed,” says Fleming. “You feel like you're in the South of France.

For many years, potato and duck farms dominated the North Fork. But in the 1970s, savvy entrepreneurs realized that the area’s maritime climate and rich soil were similar to Bordeaux. Herodotus “Dan” Damianos was one of the earliest arrivals. In 1979, the agriculture-obsessed doctor bought a potato field and transformed it into Pindar Vineyards. “At that time, Long Islanders were more into beer,” says his son Pindar Damianos, who now runs the 400-acre operation. “So we came out with easy drinking wines — and the rest is history.”

The North Fork is now covered with a patchwork of more than 30 vineyards. So where should you go? I turned to James Beard Award-winning chef Stephan Bogardus, who runs Halyard restaurant at the Sound View hotel. Bogardus also has a strong connection to this area — he grew up in Mattituck. “The beautiful thing about the vineyards of the North Fork is that they’re like the heart that's beating in the middle of this huge body of land,” says Bogardus.

Besides Pindar Vineyards and RGNY, here are four more vineyards that Bogardus recommends for an idyllic vineyard visit:

Costello di Borghese Vineyard in Cutchogue – “It's got the first plot of grapes ever grown on Long Island and my brother-in-law Giovanni personally handles all the tours on this beautiful chunk of land.”

Macari Vineyards in Mattituck – “A third-generation family-run establishment with biodynamic practices. They’re at the forefront.”

Old Field Vineyards in Southold — “A tiny plot of land with a rustic feel and an outdoor wood-fired stove. They’re able to navigate the old vines into something really magical.”

McCall Wines in Cutchogue – “Great pinot noir and rose and even cow ranching, which makes it really special. They’re doing wine in such a unique way that no one is copying down the road.”

▶️Want to listen to a winery pairing guide? Podcast: Wine Tasting on the North Fork

On the North Fork, farm-to-table is a given. Here are some of the best spots to taste what the North Fork has to offer:

Breakfast: Bruce & Son in Greenport - Breakfast is the only meal of the day at this brunch spot in a former cheese shop. The candied bacon is everything.

Lunch: Love Lane Kitchen in Mattituck - Café attached to a gourmet grocer on one of the North Fork’s prettiest streets.

Food Truck Finds: 8 Hands Farm in Cutchogue - Farm-to-food...to truck. This gourmet truck set on a family farm is open for breakfast and lunch. Don’t miss the house-made sausage.

Pizza Party: 1943 Pizza Bar in Greenport - Clam on a pizza? Trust me — try it once. This decadent pie spot is only window service due to COVID-19.

Date Night: North Fork Table & Inn in Southold - New owner John Fraser, a Michelin-starred chef, is carrying on the tradition of this restaurant that started the North Fork’s farm-to-table movement.

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