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…

  • 170 Moores Lane
  • (631) 477-0248

The Greenport Skate Park is a 20,000 sqft concrete-and-wooden outdoor facility located in Greenport, New York. Built in 1998, the park serves as a central recreational outlet for the local community and surrounding townships. Greenport Skate Park welcomes all wheels - boards, scooters, skates, and…

  • 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!

  • 41 Front Street
  • (631) 477-6811

We are an ever-evolving curated boutique filled with artisan goods and a few of our favorite things. Here, you can find a sampling of our best selling collections. For the full experience, visit us in the heart of Greenport village

  • 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…