Greenport Overnight

2 Days

Named by Forbes as one of the prettiest towns in the United States, Greenport is a popular town on the North Fork all year long. Known for its abundance of restaurants, great shopping, attractions, and more, Greenport has it all.


Day 1

  • 102 3rd St

George D Costello Sr Memorial Skating Rink is located in the heart of Greenport Village, just North of the Shelter Island Ferry/Hampton Jitney/LIRR.​ The 7,000 sq. ft indoor roller skate rink is open year round. Skate rentals available in sizes: Toddler 7 to Mens 16 or bring your own. Rollerblades…

  • 234 Carpenter Street, Greenport, New York
  • (631) 477-6681

We make every drop of Greenport Harbor beer in two small craft breweries on the North Fork of Long Island. Come visit us at our original location - an old firehouse in the heart of Greenport. Or, our tasting room and restaurant in Peconic. Be sure to bring your furry friend to our pet-friendly…

  • 326 Front Street
  • 1.631.477.0066

Greenporter Hotel is a small, privately owned Green-Certified hotel located in the heart of the North Fork’s wine country in Greenport, Long Island. The Greenporter Hotel is located in the walking Village of Greenport near most restaurants, boutiques, galleries and village docks, as well as a…

Day 2

  • 120 main St
  • (631) 477-1518

Kim Loper and Andrew LoMonaco purchased the store in 2015 at its original location on Front Street in Greenport, NY. The new owners had big plans and knew they would eventually need a larger space. When a two-story historic property on Main Street came on the market, they jumped at the opportunity…

  • 1100 Manhasset Avenue
  • (631) 268-6528

Private and public sailing charters for 1-32 guests. Step aboard the schooner Bonnie Lynn or classic yacht Surprise for an unforgettable experience on the beautiful waters of the East End!

  • 824 North Road
  • (631) 477-6977

Kontokosta Winery is the North Fork’s first and only waterfront tasting room and winery. Situated on sixty-two acres, the winery property boasts over a quarter-mile of Long Island Sound waterfront. Perched atop sweeping bluffs overlooking the region’s coastline, guests are invited to sit and enjoy…