By Anastasia Mills Healy

No need to fly across the country to winery hop or sit in Cape traffic to experience quiet seaside towns and fresh local seafood. At the end of the L.I.E. the road splits: Route 24 to the right leads to the Hamptons and Route 25 to the left meanders by the vineyards and farm stands of the North Fork. There are stretches of beach and opportunities for fishing, paddle boarding, and other water sports, but locally harvested wine and seafood are the big draws. Fall is harvest season, full of special wine dinners and apple and pumpkin picking. If you follow the left fork, there’s no need to pack designer duds—men don’t even require collared shirts at the area’s best restaurants. But don’t let the casualness fool you. Hoteliers, restaurateurs, and sommeliers are sophisticated and on their game. 


Greenport with its walkable downtown is a perfect North Fork home base. Its many spots to eat, drink, and shop within the radius of a few blocks will make you want to extend your stay. Founded in the 1600s, Greenport over the years has been a major whaling, fishing, shipbuilding, and oystering port. This village, which is a part of Southold, has retained its small-town vibe with locally owned businesses and a town green complete with antique carousel.

Hotel: The Menhaden is an upmarket, 16-room boutique hotel in Greenport’s picture-perfect town center. Extraordinarily comfortable beds, a well-regarded small plates restaurant called The Merchant’s Wife, popular coffee shop, and rooftop terrace make it a destination in itself. Snacks are available 24/7 in each floor’s Galley and a copy of Moby Dick is placed bedside in case guests are inspired by their seafaring surroundings. Hotel guests have access to bicycles and a car as well as a crackerjack concierge staff that’s only a text away. Interested in a private visit to an oyster farm, flower fields, or Shelter Island? How about a cooking class or harvest dinner? (For non-fishing folks, a menhaden is a type of herring that was once abundant in the area.)


Food: An incredible gem of a spot on the water, Little Creek Oysters is open year round and specializes in local oysters, delivered fresh every day and shucked perfectly, served with the liquor intact. In its tenth year, Noah’s is known for elevated cuisine, especially seafood and the small but mighty truffled filet mignon sliders. Hopping even at 10pm, Lucharitos is a taco joint with enticing daily specials and killer margaritas. Goldberg’s claim to fame is bagels, but its all-day breakfast is noteworthy as well. Head to Portfor your fix of avocado toast and a lobster roll (served both Connecticut and New England style).

Drink: The downtown waterfront bar and dining scene is most vibrant at Claudio’s and Crabby Jerry’s, which are next to each other. Greenport Harbor Brewing Company bucks the wine trend and produces a variety of beer; Harbor Ale is the one most spotted on area menus. Check out its second floor tasting room next to the historic Greenport Jail to find suds not widely distributed like One Love, a passion-fruit infused lager. What seafaring town is complete without a dive bar? Whiskey Wind Tavern fills this role.

Shopping: Shops with names like Tea & Tchotchkes and Fatface showcase individual style and personality with all manner of items for sale from vintage clothing to earrings with the 11952 ZIP code.

Other Pursuits: There’s a 1920 carousel on the town green, boating, fishing, golf, beaches, pumpkin and apple picking, museums, and roller skating. Take the ferry from Greenport to Shelter Island if you’ve ever been curious about this under-the-radar destination only accessible via boat. Beyond Greenport, Lavender by the Sea attracts Instagrammers in June and July for its field of gorgeous purple blooms. 


Greenport is great but let’s talk wine. The North Fork has more than 50 vineyards (covering about 2,000 acres) that offer tastings. Some are seasonal and others keep their doors open year round. The Northforker has published a comprehensive list, but here are three highlights.

Croteaux Vineyards produces only rosés and has a gorgeous open air backyard tasting area with a tree-shaded courtyard centered around wooden barns. We swear you will think you’re in Provence.

Concentrating only on effervescent wines, Sparkling Pointe offers a tasting menu of its bubbles paired with chocolates. A modern room with a fireplace and a crystal chandelier dangling from a high ceiling overlooks a patio and rows upon rows of grape vines.

This area’s only winery on the water, Kontokosta has a spacious building for tastings and a flat green lawn that ends at ocean bluffs and the Long Island Sound. Many wine styles are produced here including a crisp viognier and a smooth cabernet sauvignon.


Greenport’s East End Seaport Museum is producing the 30thAnnual East End Maritime Festival September 20-22. The Land and Sea Gala kicks off the weekend, which includes a parade, kayak races, boat cruises, tours of Bug Lighthouse, and a Chowder Contest. Beer lovers will be in heaven at the Long Island Hop Fest September 21. Sparkling Pointe’s Vintner’s Harvest Dinner is September 22. A family event, Wildwood Fall Festival is September 28 as is the Macari Wine Dinner at the Halyard, the restaurant at Greenport’s Sound View Hotel. All About Harvest wine talk and dinner at Lenz Vineyards in Peconic and Harbes Family Farm Pumpkin Festival in Mattituck are both scheduled for October 3. On October 4, Castello di Borghese is offering a Founders Tour, a small private winery tour followed by a wine tasting paired with cheeses. The Southold Historical Society’s Autumn in the Air Party featuring live music, wine, beer, and food is also on October 4. Not quite on the North Fork but worth mentioning, Blue Point Brewing Company’s Oyster Ball is October 5. The Big Band and Rock and Roll Car Show is October 6 on the Cutchogue Town Green.

Getting There

Drive time is two and a half hours from Greenwich. There’s a ferry from Bridgeport to Port Jefferson: Travel time is 1 hour 15 minutes, and driving timefrom Port Jeff to Greenport is one hour. The crossing from New London to Orient Pointis one hour and 20 minutes or 40 minutes via high-speed ferry if you’re not taking your car. Orient Point to Greenport is 15 minutes via car.

Tourism Info

Greenport Tourism Info

North Fork Tourism Info


Photo Credit: Read McKendree and