Relaxing Wine-Tasting Weekend on Long Island's North Fork

  • Distance from Philadelphia: 99 miles
  • Best time: May to October
  • Best for: Girl's GetawayRomanticFood and Wine

After years of playing second fiddle to Long Island's glitzier South Fork (home to the Gatsby-esque mansions and celebrity haunts of the Hamptons), the pastoral, vineyard-studded North Fork is making headlines not only for its Chardonnays and Merlots but also for its innovative farm-to-table cuisine and inviting inns. By turning north rather than south at the end of the Long Island Expressway, you'll be forced to mentally and physically slow down as you stop at roadside farm stands selling just-picked fruits and vegetables, breathe in the irresistibly salty sea air, linger over innovative menus designed by rising star chefs and—of course—sip the increasingly impressive wines. Strung along Rt. 25, the North Fork's 11 picturesque towns (including Southold, Cutchoque, Mattituck, and Greenport) harbor more than three-dozen wineries and at least as many historic white churches. There are also lovely beaches (for sunning) and bays (for kayaking), making a weekend here the perfect antidote for big city (or even suburban) stress. Here's how to enjoy this farmland's natural beauty and bounty. –By Donna Heiderstadt


North Fork Cheat Sheet

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1.Before you leave, check the schedule of the Long Island Wine Council for Friday evening winery events such as Shinn Estate Vineyards in Mattituck ($9-13 glasses of organic wine and cheese plates) or Dilberto Winery in Jamesport .

2.Continue your evening in Greenport, the North Fork's prettiest and liveliest town, at Chowder Pot Pub to enjoy the sunset over Peconic Bay. The live music and outdoor seating are perfect additions to a casual night out.

3.Or, if you're hungry for a serious meal, have dinner at The Frisky Oyster, where chef-owner Robert Beaver creates modern, sophisticated cuisine (seared scallops with roasted golden beet risotto, filet of beef with lobster and potato hash), but with a sense of humor (oysters "Friskafella" with garlic-scented spinach, chipotle, and parmigiano aioli).


1.Fuel up with breakfast at your inn or condo, or head to Love Lane Kitchen, located on Love Lane just off Rt. 25 in Mattituck, for the hearty challah French toast or made-to-order omelets.

2.Rent a double kayak from Eagle's Neck Paddling Company in either Orient Beach State Park or in the Port of Egypt Marina, in Southold, and paddle across bays and estuaries where you can spot abundant wildlife, like heron, osprey, egrets, kingfishers, and even deer and red fox.

3.Take a break from the sea air and sun with a lunch at Noah's in Greenport as you sample a variety of small plates (gorgonzola-rosemary fries, crispy Tasmanian red crab tacos) as well as oysters and clams from the raw bar.

4.Spend a pleasant half hour perusing the boutiques on Greenport's Main Sreet and Front Street. Check out Doofpot for European ceramics, Verbena for unique design items, and The White Weathered Barn for charming artisanal crafts.

5.Now it's time to winery hop along the North Fork Wine Route (Routes 25 and 48). With about 40 wineries to choose from (frequently marked with signs), you can't possibly hit them all. Stick to our top picks and you'll taste some of the best. Visit Paumanok Vineyards in Aquabogue, one of the North Fork's oldest wineries (founded in 1983), for lovely estate-bottled Bordeaux-style blends and crisp Rieslings and Chenin Blancs. On Rt. 48 (Sound Ave.), stop by Macari Vineyards in Mattituck to sample its array of Merlots, Cabernet Francs, and Riesling in an airy tasting room with fireplace and vineyard views.

6.If you'd like to keep your driving to a minimum, center yourself on Rt. 25 (Main Rd.) in Cutchogue, Southold and Peconic and visit Bedell Cellars, where 30-year-old vines produce award-wining wines such as a flagship red-blend Musée; Osprey's Dominion Vineyards whose convivial tasting room (try the highly rated 2007 Reserve Merlot) features live-music every Saturday; Raphael where an atmospheric Old World tasting room sets the scene for a unique 2012 Chardeaux (Chardonnay and Sauvignon Blanc blend); and & Croteaux Vineyards, whose charming tasting barn and courtyard will entice you to chill out while comparing a variety of refreshing rosé wines.

7.Keep channeling the spirit of the local vineyards and farmland by enjoying a three-course dinner at The North Fork Table & Inn in Southold, where Chef Gerry Hayden (a 2012 James Beard Award nominee) creates dishes based on locally caught or farmed ingredients seasoned with terrific flavors (like crispy Peconic Bay sea bass with Peconic Bay clams, saffron-braised fennel, picholine olives, and spicy clam broth).


1.Sleep in. When you rise, head over to Lavender by the Bay, a 10-acre farm in East Marion to meander through the gardens, pick up dried cooking lavender and calming lavender sachets and lotions.

2.Grab a delicious "brunch on a bun" (perfectly prepared lobster roll), locally grown North Fork potato chips, and passion fruit iced-tea to go at Southold's The Lunch Truck before working your way back home, stopping at the many farm stands along Rt. 25 that sell fresh fruits and vegetables from June to October.

3.Since you're so close, swing by the Tanger Outlets in Riverhead for designer bargains at Coach, Polo Ralph Lauren, Michael Kors, and others. Justification: you need a new bag to tote all of the local wines you've just bought.

Where to Stay

With a fabulous location offering easy access to both Greenport and a dozen nearby wineries, the intimate, four-room The North Fork Table & Inn(rooms from $250/night) in Southold is ideal for couples (and you can have a great meal right downstairs). For a girls' getaway, Greenport's Cliffside Resort Condominiums (from $434/night) offers two-bedroom condos that sleep up to six, with full kitchens, balconies, and easy access to local bars and eateries.

For a special occasion or a romantic splurge, opt for the Jedediah Hawkins Inn in Jamesport (rooms from $325/night). This six-room Victorian inn is the former home of a 19th-century sea captain and has been restored to its former glory with interior designer touches, sumptuous linens, in-room fireplaces, and two fantastic restaurants: Luce + Hawkins, and Luce's Landing.

When to Go

Summer and Fall are the two main seasons on the North Fork, when its wineries buzz with visitors (expect traffic jams on weekends, especially during the late September/early October harvest period) and its roadside farm stands burst with fresh corn, cabbage, strawberries, watermelons, peaches, and more. On holiday weekends, rooms tend to sell out weeks in advance.

For lighter crowds, visit in spring as the vines begin to blossom and tasting rooms gear up for the summer rush. The North Fork is quite laid-back in winter (plus there are great lodging deals) making it an ideal destination for a relaxing weekend of winery visits and fine dining.

How to Get There

By car from New York City: The North Fork of Long Island is about a two-hour drive from New York City, but it can take much longer depending on traffic. Take the Long Island Expressway (I-495) East to exit 71. At the end of the ramp, turn left onto Edwards Ave., heading North to Sound Ave. Turn right onto Sound Ave. and continue to the Rt. 48/Sound Ave. wineries, or turn right onto Rt. 105 and then left on Rt. 25 for the Main Rd. wineries.

By train from New York City's Penn Station: The Long Island Railroad offers several trains a day from Penn Station via its Ronkonkoma/Greenport branch, with stations in Riverhead, Mattituck, Southold and Greenport. Travel time is approximately 2.5 to 3 hours.

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