greenport - tour the neighborhood

Beautiful hamlets, towns, and islands near Greenport village are easily within reach.


East of Greenport there are three Orients. Orient Point is Long Island's “gateway to New York State” with ferry service to Orient Point from New London, CT, daily, (631) 323-2525. The hamlet of Orient includes Orient Point and the charming village of Orient. From Greenport, take Main Street (Route 25) North to the blinking light (Route 48). Make a right toward Orient. Follow Route 48 for approximately 4.5 miles. On your way to Orient, enjoy the beautiful water views and stop for local farm fresh flowers or produce. See the famous Orient Point Lighthouse or spend a day playing on the beach at Orient Beach State Park. In Orient village travel back in time through its majestic historic district.


West of Greenport along Route 25 are the downtown centers of Southold, Cutchogue and Mattituck (in that order) where you will find quaint shops, eateries and history every step of the way. In Southold, visit the Custer Institute Observatory (631) 765-2626 and gaze at the stars. Just follow Route 25 West from Greenport for 5.5 miles and veer left onto Main Bayview Road. Custer Institute is on your left. Across the street, you'll find the Southold Indian Museum (631) 765-5577. In Cutchogue, visit Fort Corchaug and Downs Farm Preserve (631) 734-6413, a 51-acre natural and historic resource that encompasses a Native American fort site, scenic woodlands and tidal wetlands. Then take Route 25 West and stroll down historic Love Lane in Mattituck, which features many quaint shops and eateries.

Shelter Island

Just a ferry ride away from the Greenport village, via the North Ferry Company (631) 749-0139, Shelter Island offers the perfect getaway where you can stroll down historic tree-lined streets, take in breathtaking water views, eat at one of the island's fine restaurants and even play a round of golf. Boats leave approximately every 15 minutes. Take your car and explore all the beauty that the island has to offer. If you decide to walk or bike, the town of Derring Harbor, a short walk from the ferry has restaurants and shops.