Southold, NY Road Trips

The town of Southold covers most of the "North Fork" or northeastern peninsula of Long Island. It is more rural in character than most parts of Long Island and is well known for its wineries, farms, and fishing towns. The town's main settlement is the village of Greenport, but it also contains the hamlets of Cutchogue, East Marion, Fishers Island, Laurel, Mattituck, New Suffolk, Orient, Peconic, and Southold.

Although there are a few wineries on the South Fork of Long Island, the Hamptons, the vast majority are located on the North Fork of Long Island. Greenport Skatepark, Ice Skate Rink & Carousel, Greenport, ☏ +1 631 477-1133. Strong's Marine, LLC, Camp Mineola Road, Mattituck, ☏ +1 631 298-4770. This place allows for renting boats and does provide boating lessons. Harbes Family Farm, 715 Sound Ave. (Rte. 48), Mattituck, ☏ +1 631 298-0800. Allows you to pick your own fruit and vegetables as well as flowers. It is open from May till October. The months depend on what you are able to pick. The North Fork of Long Island has many beaches as well as park trails. As well as these beaches and park trails, the North Fork of Long Island is known for their many wineries as well as a small knit community. Sannino Vineyard B&B, 7490 Alvahs Ln (North of RT 48), ☏ +1 631-734-8282. all year. An exclusive Tuscan Suite on a private vineyard Private entrance and balcony overlooking the vineyard King Size bed, 700 sq. feet of luxury Breakfast in Bed $300 avg. Orient Beach State Park, 41425 NY-25, Orient, ☏ +1 631-852-3232. 6AM-8PM. Small waterfront Park known for its pristine views of Long Island Sound and ample fishing. (updated Feb 2024) Horton Point Lighthouse Nautical Museum, 3575 Lighthouse Rd, ☏ +1 631-765-5500. Local history museum housed in an 1857 lighthouse. $5. (updated Feb 2024)

A Touch of Venice, 2255 Wickham Avenue, Mattituck, ☏ +1 631 298-5851. Braun Seafood, 30840 Main Road, Cutchogue, ☏ +1 631 734-7770. Claudio's Clam Bar & Wharf, Main Street Wharf, Greenport, ☏ +1 631 477-1889. Claudio's Crabby Jerry's, Main Street Wharf, Greenport, ☏ +1 631 477-8252. Claudio's Restaurant, Main Street, Greenport, ☏ +1 631 477-0627. Greenport Tea Company, 400 Main Street, Greenport, ☏ +1 631 477-8744. Greenporter Bistro and Wine Bar. Legends, 835 First Street, New Suffolk, ☏ +1 631 734-5123. Lick-itty Splitz, Rte. 25, Mattituck, ☏ +1 631 298-0416. Love Lane Kitchen, Love Lane, Mattituck, ☏ +1 631 298-8989. O'Mally's Restaurant, Rt. 48, Southold, ☏ +1 631-765-2111. The Old Mill Inn, 5775 West Mill Road, Mattituck, ☏ +1 631-298-8080. Orient by the Sea, Main Road, Orient, ☏ +1 631 323-2424. Paganos, Route 25, Southold, ☏ +1 631 765-6109. The Old Mill Inn, 5775 West Mill Road, Mattituck, ☏ +1 631 298-8080. Southold Fish Market, 61859 Main Road, Southold, ☏ +1 631 765-3200. Starbucks, Mattituck Plaza Route 25, Southold.

The entire town is included within the North Fork of Long Island American Viticultural Area and is a popular destination for wine tourism. Ackerly Ponds, 1375 Peconic Lane, Peconic, ☏ +1 631 765-6861. Bedell Cellars, Main Rd., Rte. 25, Cutchogue, ☏ +1 631 734-7537. Castello Di Borghese, Rte. 48 & Alvah's Lane, Cutchogue, ☏ +1 631 734-5111. Comtesse Therese, 1375 Peconic Lane, Peconic, ☏ +1 631 871-9194. Corey Creek Vineyards, Main Rd., Rte. 25, Southold, ☏ +1 631 765-4168. Croteaux Vineyards, 1450 South Harbor Rd., Southold, ☏ +1 631 765-6099. Duck Walk North Vineyard, Rte. 25, Southold, ☏ +1 631 765-3500. Harbes Vineyard, Sound Ave., Rte 48, Mattituck, ☏ +1 631 298-0700. Laurel Lake Vineyards, 3165 Main Road, Rte 25 Laurel, ☏ +1 631 298-1420. The Lenz Winery, Main Road, Rte 25, Peconic, ☏ +1 631 734-6010. Lieb Family Cellar, 35 Cox Neck Road, Mattituck, ☏ +1 631 298-1942. Macari Vineyards and Winery, 150 Bergen Avenue, Mattituck, ☏ +1 631 298-0100. The Old Field Vineyards, 59600 Main Road, Southold, ☏ +1 631 765-0004. Osprey Dominion Winery, Main Road, Rte 25, Peconic, ☏ +1 631 765-6188. Peconic Bay Winery, 31320 Main Rd., Rte 25, Cutchogue, ☏ +1 631 734-7361. Pelligrini Vineyards, 23005 Main Rd., Rte 25, Cutchogue, ☏ +1 631 734-4111 ext 202. Pindar Vineyards, Main Rd, Rte 25, Peconic, ☏ +1 631 734-6200. Pugliese Vineyards, 34876 Main Road, Rte 25, Cutchogue, ☏ +1 631 734-4057. Raphael, 39390 Main Road, Rte 25, Peconic, ☏ +1 631 765-1100.

The Long Island Rail Road offers service on the Main Line - Greenport Branch. 1 Mattituck Station. (updated Feb 2024) 2 Southold Station. (updated Feb 2024) 3 Greenport Station. Eastern terminus of the Long Island Rail Road. (updated Feb 2024) The Cross Sound Ferry offers service from New London, Connecticut to Orient. 4 Orient Point Ferry Terminal, 41270 Main Rd, Orient. (updated Feb 2024)