Long Island Wine Country
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About the Area


The far eastern end of Long Island, home of the north fork, with its beautiful beaches, quaint historic towns and sprawling farmlands has been attracting tourists for hundreds of years. It is conveniently located just east of New York City and South of Connecticut and Boston, and easy to reach from both locations. Its climate is moderated by the bodies of water that surround it, and this moderation, combined with fertile soil from ancient glacial deposits has attracted a proliferation of vineyards on the North Fork, which have further enhanced the bucolic landscape.

The eastern part of Long Island ends in two narrow forks, often described as looking like the tail fins of a fish and named the north and south forks. The south fork is bordered by the Atlantic Ocean with wide sandy beaches and rolling surf. It is 'a Hollywood East' known for its wealthy and famous residents, mansions hidden by giant hedges, glitz, glamour and hustle and bustle in high season.

The north fork could be thought of as the south fork's beautiful demure sister. Pastoral and pristine, the north fork is surrounded by gentler more protected waters; Long Island Sound to the north and the Great Peconic  and Shelter Bays to the south.

Traveling east from Riverhead on route 25 you will pass through a series of one light, main street USA villages that have been here since the early 1700's. On the north road, Sound Avenue to Route 48 the countryside remains more rural with views of farms, vineyards, open spaces and rustic buildings reminiscent of an Andrew Wyeth Painting.

Crossing route 105 you will first pass throughout the villages of Aquebogue and Jamesport, each lined with their own unique restaurants, antique stores and boutiques. Laurel Hamlet is next; without a village center per se it has an early one room post office and old school house still in operation. Signs for 'Love Lane' announce that you have reached the picturesque downtown of Mattituck, home to the Love Lane Kitchen, the Village Cheese shop, boutiques for home and fashion goods and close by to the North Fork Theatre which produces excellent live performances throughout the year.

The next two villages, Cutchogue and Peconic are wine country central, with the greatest concentration of wineries and vineyards as well as historic churches and beautiful views. Southold Hamlet, the original settling place of the founding fathers of Southold Township is next and famous for uncluttered beaches on bay and sound, an historic district celebrating the many picturesque house and farm buildings that can be toured along its tree lined streets, a museum and gift shop, the famous Custer Institute Observatory and Horton's Point Lighthouse.

Greenport is the final village on the south road; an historic fishing community which rivals Newport for its picturesque architecture, fine shops and restaurants. Mitchell Park overlooks the park and is puprosed as the 'village green' with an enclosed 19th century carousel, an ice skating rink in winter and a center for musical performance, dances and the Greenport Maritime Festival in summer and fall. Greenport is also home to the Maritime museum housed in the historic train station. The Long Island Railroad, with service to points west and New york city still operates out of here as does the ferry to Shelter Island and the Hamptons, a quicker way to get to the the south fork than driving around. This spot is also the terminus for the Hampton Jitney bus service to New York City with stops at most villages along the way and express from Riverhead

To continue east through the villages of East Marion, Oyster Ponds and Orient, travel north from Greenport on Main Street to route 48. East Marion is the starting point of the designated National Landmark area for it's natural beauty and the historic significance of its buildings and architecture. You will pass many 18th century sea captains houses along the way, and on any of the side roads that might divert you, as well as nature preserves and beaches. Crossing the causeway to Orient, the view of open sky and sea is breathtaking in any weather or time of year and at this point the land starts to narrow towards the tail end of the fish.

As you approach the furthest tip, home to the Cross Sound Ferry which operates between New London and Connecticut, you will pass the entrance to the Orient Point State Park, a place of great natural beauty that is never crowded one of the best kept secrets on the Island. If you must leave us, the ferry is right there, but the chances are you will just want to turn around and do it all again, or like our NFBBA members, never leave.



From Points West:
Take the Long Island Expressway (I-495) eastbound to the last exit (#73, Rt. 58 Greenport-Orient).
Follow Rt. 58 to traffic circle in Riverhead (approx. 3 miles). Go halfway around circle and straight out other side.
Rt. 58 will become Rt. 25 east. Rt. 25 will pass through the towns of Aquebogue, Jamesport, Laurel, Mattituck, Cutchogue, Peconic, Southold, and Greenport.
Rt. 25 turns left at a blinking light in downtown Greenport.
Follow north for 1 mile to another blinking yellow light. Bear to the right. Continue east for the towns East Marion, Orient, and Orient Point (ferry terminal).

From Points East:
From New England, and the Orient Point Ferry, take Rt. 25 west for approx. 8 miles. You pass Orient and East Marion. At a blinking yellow light, make a left and continue for one mile into Greenport. In downtown Greenport, at another blinking light, make a right. Continue west through Southold, Peconic, Cutchogue, Mattituck, Laurel, Jamesport, Aquebogue, and finally Riverhead.

* Helpful Travel Tips:

  • It takes approx. 75 minutes to travel from NYC to Riverhead on I-495
  • Travel from the Port Jefferson ferry to Riverhead, on I-495, will take 40 minutes.
  • Islip Macarthur airport is 30 minutes to Riverhead.
  • From Riverhead to the Orient Ferry is 40 miles.
  • The Bed & Breakfasts of the North Fork Wine Country area are spread between Jamesport and Orient.
  • Follow your B&B's specific directions when you reach the town they are located in.