The North Fork: The East End’s Road Less Traveled

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Wine lovers can taste their favorites among the vines on the North Fork
Getty Images

When it comes to the East End, much of the fanfare goes to the South Fork but visitors who favor tranquility, natural beauty, less traffic, and more wine in their weekend getaways, consider taking Route 25 east of Riverhead into the heart of the beautiful and underappreciated North Fork.  

The area is composed of two towns — Riverhead and Southold — containing within them 18 beautiful and diverse hamlets and one incorporated village: Greenport. While each destination has its own unique characteristics, the overarching themes of the North Fork are rural allure, small-town charm, and world-class wine.

“The North Fork is its own culture of people who prefer a slower-paced lifestyle that’s as rich in agriculture as it is in style,” Rena Wilhelm, chairperson at Greenport Skate Park. and longtime North Fork resident tells us. “The area is blessed with beautiful landscapes of farmland, the Long Island Sound, and Peconic Bay, and because of that environment, I believe people are just more at ease and therefore kinder.”

If that sounds like an alluring weekend destination, then be sure to add some of the following to your itinerary:

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An aerial view of GreenportGetty Images


While some consider the North Fork an overlooked gem, wine connoisseurs tend to give the area its due. It is frequently namechecked in nationwide wine region rankings, which is easy to understand for anyone who’s ever been to one of the region’s over 40 wineries. 

Visitors won’t have to travel far on the North Fork to find RGNY (6025 Sound Ave., Riverhead, 631-298-0075, rgnywine.com), one of the area’s most exciting new vineyards. This female-led sustainable operation is part of the famed Rivero Gonzalez family of winemakers. 

Further east, in the village of Greenport, is the beautiful Kontokosta Winery (825 North Rd., 631-477-6977, kontokostawinery.com) which offers stunning views of the Sound that pair incredibly well with their selection of renowned wines.

The North Fork is also a haven for great breweries. Riverhead hosts several of the area’s finest, including North Fork Brewing Co. (24 E 2nd St., Suite A, 631-591-1191, northforkbrewingco.com) and Jamesport Farm Brewery (5873 Sound Ave., Riverhead, 844-532-2337, jfbrewery.com) the former of which collaborates with local farms to create one-of-a-kind brews that are uniquely North Fork.

Autumn is the exact time of year when a crisp hard cider tastes its absolute best. If a festive sip of seasonal spice is what you seek, then the tasting room at Woodside Orchards (729 Main Rd., Aquebogue, 631-722-5770, woodsideorchards.com) is the place. 


The Menhaden Hotel (207 Front St., Greenport, 631-333-2777, themenhaden.com)

The Shoals Suites and Slips (61600 Main Rd., Southold, 631-765-5121, theshoalsnorthfork.com)

Sound View Greenport (58775 County Road 48, Greenport, 631-477-1910)


It’s best to eat a big meal before going on a lengthy wine or brew tour, so be sure to stop at one or more of the following local spots. 

North Fork Doughnut Co. (100 Love Ln., Mattituck, 631-298-7941, nofodoco.com), also known as No Fo Do Co, can be found on Mattituck’s famed Love Lane. They’ve got some of the island’s best donuts, with a menu that includes time-honored favorites as well as some more daring selections.

Lucharitos has become a local staple over the last decade. It began in 2012 as a little taco spot in Greenport (119 Main St., 631-477-6666, lucharitos.com) and has since expanded to three North Fork locations: Center Moriches, Mattituck, and Aquebogue, as well as one in Melville. They offer a delicious blend of modern and traditional Mexican menu items. 

Lucharitos’ latest endeavor is Lucha Cubano (87 E Main St., Riverhead, 631-591-3575, luchacubano.com). The colorful Cuban spot, which occupies the building where the famed Riverhead Diner & Grill once stood, opened for business earlier this year. 

Visitors are never far from fantastic seafood when on the North Fork. Little Creek Oyster Farm & Market (Bootleg Alley, 37 Front St., Greenport, 631-477-6992 littlecreekoysters.com) has everything you’re looking for in a maritime menu: oysters, clams, chowder, smoked fish, and more. 

It’s nice to enjoy the finer things when on vacation. Southold Social (56125 Main Rd., Southold, 631-765-8888), which opened just this past June, offers exactly that. Run by James Beard Chef François Payard, this beautiful new spot is a perfect example of why tourism in Southold has been trending upwards. 

“Southold town takes a great deal of pride in its community,” Southold Town Supervisor Scott Russell tells us. “Seeing such growth in our tourism is understandable because of how hard we’ve worked to make it a destination.”

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Harbes Orchard


Bucolic beauty is a calling card for the North Fork and there is no better time of year to appreciate it than the fall. Travelers come from all around to pick up some of the island’s freshest produce and enjoy some seasonal festivities, namely pumpkin picking.

Jamesport Farmstead (1192 Main Rd., 631-561-9810, jamesportfarmstead.com) is one of the newest agricultural attractions in the area. This little organic farm produces big yields of all kinds of fresh fruits and veggies with their hands-on no-till method. They’re open every Saturday, with online orders available for pickup from 12-4 p.m. on Fridays. 

When it comes to North Fork pumpkin picking, we’d be remiss not to mention the iconic Harbes Family Farm (715 Sound Ave., Mattituck, 631-298-0800, harbesfamilyfarm.com) but be warned that during this time of year they can be impressively busy. 

If you’re looking for an other pumpkin-picking options, there are plenty, including Stakey’s Pumpkin Farm (270 West Ln., Aquebogue, 631-722-3467, stakeyspumpkinfarm.com) and Gabrielsen’s Country Farm (200 Herricks Ln., Jamesport, 631-722-3259, gabrielsenscountryfarm.com

Stephanie Gabrielsen, daughter of Gabrielsen’s Country Farm owner Carl Gabrielsen, says they offer a lot more than pumpkin picking.

“We have lots of pumpkins,” she tells us, “but we also have a lot of hardy mums to choose from, we have asters and cabbage and kale, we have celosia, sweet corn, and apples.”

If apples are what you and your family prefer to pick, then Woodside Orchards (116 Manor Ln., Jamesport, 631-722-5770, woodsideorchards.com) is your spot. Pick your own from the orchard, grab some fresh cider, or order apple-based baked goods like pie or donuts.


Case’s Place (650 1st St., New Suffolk, 631-734-8686)

Barrow Food House (452 Main Rd., Riverhead, 631-779-3379, barrowfoodhouse.com)

North Fork Table & Inn (57225 Main Rd., Southold, 631-765-0177, northforktableandinn.com)


Appreciation for the arts is something that’s inherent in the North Fork. The area favors the handcrafted, admires the uncommon, awards the different, and honors natural beauty. It also has some really cool artsy destinations. 

Greenport Skate Park (Moore’s Ln., 631-477-0248, www.greenportskatepark.org) has been part of the community for many years, but it just recently started playing host to more than just the art of disobeying gravity. This past summer they held their first Sound & Skate Festival, which featured live music, skating, vendors, and a live graffiti-mural competition. 

Chairperson of Greenport Skate Park, Rena Wilhelm believes this event and future ones are an opportunity for the village of Greenport to better express itself. 

“Hosting a festival whose sole purpose was to shine a light on how important this park is to the community was the perfect way to help put Greenport on the map for something other than our bars and restaurants,” she tells us, “and because art & music are so closely tied to the entire skating culture, it was the perfect combination for residents and visitors alike to see what we could offer that was different.”

The murals created in that competition were donated by the artists to be auctioned off on Saturday, Oct. 22 at the Art Exhibition & Makers Market to raise money for the skatepark’s rehabilitation. The event will take place at George D. Costello Sr. Memorial Skating Rink (102 3rd St., Greenport) and will feature over 40 different vendors, some of whom are the artists who created the featured canvases. 

There will also be a Sk8tober Pop Up event at Greenport Skate Park on Saturday, Oct. 15 with skating, live music, food, and vendors.

For some North Fork pastoral serenity-turned-art, check out the Landcraft Garden Foundation (4342 Grand Ave., Mattituck, 631-298-7216, landcraftgardenfoundation.org). This astounding garden of rare and unusual plants is a horticultural wonder that’s open Fridays and Saturdays until Oct. 29.  

In terms of North Fork fine art, Natali/Keyes at the Fiedler Gallery (207 Main Street, Greenport, 631-506-9490) offers a new vision for a well-known local art destination.

The beloved gallery’s future was uncertain after manager Richard Fiedler died in 2018 until local art lovers Lucas Natali and Julie Keyes took up the mantle late last year and began holding their own contemporary art exhibits at the gallery. It’s worth a look for any admirer of the arts.


A day trip to the North Fork is definitely doable, but if you really want to take it all in, then an overnight stay may be in order. Fortunately, there are more than a few amazing places where you can do that.

North Fork Table & Inn (57225 Main Rd., Southold, 631-765-0177, northforktableandinn.com) combines the kitchen of Michelin-starred Chef John Fraser with a boutique four-room hotel right on the Long Island Sound.

Sannino Vineyard Bed & Breakfast (15975 County Rd. 48, Cutchogue, 631-734-8282, sanninovineyard.com) offers a similar experience, only rather than fine dining you’ll enjoy fine wine during your romantic overnight stay in the heart of a beautiful North Fork vineyard.