48 Hours on Long Island's North Fork

Long Island's vineyard-studded North Fork is the perfect weekend getaway for families, food and drink enthusiasts, and anyone who appreciates scenic seaside villages. Spend your weekend sampling the region’s award-winning varietals and locally made dishes, then hit the beach for a sun-soaked day on the Long Island Sound. Here's your guide for a relaxing 48 hours among the blissful coastal communities of the North Fork.

This article was last update on May 22, 2026.

FRIDAY 

4 pm: Explore Scenic Greenport 

If you're looking for live music, charming boutiques, and restaurants with outdoor terraces, head to Greenport, a vibrant waterfront village where an adorable historic district and working marina create an enchanting afternoon and evening. Start by trying the local craft beers at Greenport Harbor Brewing Co., which has a tasting room housed in an old firehouse right in Greenport at 234 Carpenter Street. Then head over to Mitchell Park, where you can take the kids for a spin at the 100-year-old Jess Owen Carousel House ($3 per ride) or discover the rich maritime heritage of Long Island's East End at the East End Seaport Museum.

7 pm: Dine in Greenport

For dinner, Claudio's is bringing a fresh new experience to Greenport's iconic waterfront. Savor dockside dining, fresh seafood dishes, and over-the-top cocktails at Claudio's Waterfront; classic coastal fare, tavern staples, and New York-style pies courtesy of Peter's Pizzeria at Claudio's Restaurant; and sunset cocktails with European beach club vibes at Saylor Beach House. For a contemporary farm-to-table experience, head to Noah's, where a seasonally rotating menu highlights local farmers, growers, and fisherman with a wine list that spotlights bottles from nearby vineyards. The North Fork is also a hub for fresh local oysters. For a taste of the local delicacy, visit Little Creek Oyster Farm & Market at their new location at 211 Carpenter Street for a shucking lesson and raw bar experience.

SATURDAY

9 am: Grab a Bite at Love Lane Kitchen   

Fuel up at Love Lane Kitchen, right off Route 25 in Mattituck, where a menu full of mouthwatering breakfast items like challah French toast and made-to-order omelets will leave you ready to conquer the day. Grab a sandwich or salad to go for lunch—you'll be spending most of the day partaking in beach activities or wine-tasting. Both options will work up a serious appetite.

11 am: Take a Walk on the Beach

Go for a walk or simply enjoy the views of Gardiner's Bay at Orient Beach State Park, recognized by Travel + Leisure as one of the best secluded beaches in the United States. The park is home to a rare maritime forest of red cedar, black-jack oak, and even prickly-pear cactus, and is recognized as an Audubon Important Bird Area, making it a top spot for watching great blue herons, egrets, and osprey. During the summer season, rent a kayak or paddleboard from Eagle's Neck Paddling Company, located right inside the park.

1 pm: Visit wine country

With more than 60 wineries in Long Island's Wine Country, the North Fork offers a selection of vineyard experiences for every taste and style. A few spots to get you started include:

• Bedell Cellars (Cutchogue) — A picturesque winery with a barn-style tasting room open Sunday–Thursday 11am–6pm, Friday & Saturday 11am–7pm. Fun fact: their merlot was served at President Barack Obama's inauguration.

• Kontokosta Winery (Greenport) — The North Fork's only waterfront winery, perched on sweeping bluffs overlooking the Long Island Sound. Open every day 11am–5pm, walk-ins welcome.

• Pindar Vineyards (Peconic) — Long Island's largest winery, known for in-depth behind-the-scenes tours and a sprawling sunflower field.

• Sparkling Pointe (Southold) — The only Long Island winery dedicated to exclusively producing sparkling wines in the traditional Méthode Champenoise, ideal for celebrations.

Pro tip: Consider booking a guided wine tour with companies like New Vine Wine Tours, which handle transportation so you can sip without worry.

4 pm: Sail for Shelter Island, or go shopping in Greenport Village

Take the North Ferry to Shelter Island and soak in the region's seaside charm. Check out the historic Pridwin Hotel and Cottages, classic American resort hotel nestled on 10 waterfront acres on Crescent Beach that has been providing guests a unique coastal retreat since 1927, or venture to Mashomack Nature Preserve for miles of sandy coastline and peaceful woodland trails.

Let the ferry take you back to Greenport's Main Street and Front Street to peruse boutiques and antique shops for clothing and decor pieces created by the area's artists and artisans. 

7 pm: Dine out in charming North Fork villages

The North Fork is a close-knit community filled with family businesses and farm-to-table restaurants. Head to The Halyard at Sound View in Greenport (pictured) for spectacular sunsets over the Long Island Sound paired with fresh, local fare under the direction of Culinary Director Chef Francis Derby. In the town of Southold, the celebrated North Fork Table offers seasonally-inspired American dishes and an elegant ambiance. For your after-dinner cocktail back in Greenpoint, Brix and Rye has outstanding mixologists and live music all night long.

SUNDAY

9 am: Start the day at North Fork Roasting Co.

Head to North Fork Roasting Co. in Southold for a standout start to your morning. Open daily from 7am to 4pm, this beloved coffee shop serves freshly roasted coffees alongside nourishing breakfast bites like the Avocado Smash (mashed avocado on toasted country white bread with roasted corn, pickled onions, radish, cilantro, and everything seasoning) and the Acai Bowl (blended acai berries, banana, almond milk, homemade granola, roasted coconut, and agave.

11 am: Take selfies at Lavender by the Bay  

Head over to Lavender by the Bay in East Marion. It's New York's premier lavender farm and one of the largest in the entire country—as well as one of the best selfie spots on the North Fork! Meander through the gardens and enjoy a snack in the fields, all the while soaking in the sunshine and taking in the beautiful scents. While the lavender fields are typically in bloom in June and July, you can visit the farm from April to December to purchase lavender-scented soaps, sachets, lotions, bath salts, and more.

Lavender by the Bay also a second location a bit further west in Calverton at 536 Middle Country Road, which is a great option for summer visits with kids, as it's situated across from Splish Splash water park.

1 pm: Experience family fun at Harbes Family Farm

With three locations on the North Fork, including a farm and vineyard in Mattituck (pictured), this family-run farm has offered fresh produce and more for 30 years. The farm hosts memory-making apple- and pumpkin-picking experiences in season, as well as family fun such as hayrides and corn mazes. The winery is a must-visit for anyone who wants to experience the North Fork terroir; Harbes has earned major awards for its sparkling blanc de blancs and several red varietals (Syrah, merlot, and cabernet franc). 

2 pm: Shop at Tanger Outlets    

Before you go home, stop by the Tanger Outlets in Riverhead for designer bargains including brands like Coach, Polo Ralph Lauren, and Michael Kors.

GETTING THERE

By train or bus:
Take the LIRR to Greenport station. By bus, check out the Hampton Jitney schedule.

By car:
   • From New York City: 2.5 hours
   • From Albany: 4 hours
   • From Boston, MA: 4 hours
   • From Philadelphia, PA: 4 hours 

By plane:
Fly into Long Island MacArthur Airport then catch a 40-minute cab or shuttle to the North Fork.

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