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72 Hours in Greenport

Less than three hours from New York City, Greenport is a relaxing getaway from city life. Whether you’re visiting New York or a city dweller, beat the heat this summer with the breeze off the Long Island Sound and relax in Greenport’s laid-back restaurants, bars and wineries.

Day 1

3PM: Orient Beach State Park

Featuring an expansive beach and one of the most pristine maritime forests on the North Fork, spend the afternoon swimming, kayaking, canoeing, or bike riding around the park.

Driving distance from Harborfront Inn: 18 minutes

4PM: Check in at the Harborfront Inn at Greenport

6PM: Greenport Harbor Brewing Co.

At the very end of Long Island, every drop of Greenport Harbor Beer is made in two small craft breweries. Try year-round beers on top like the American IPA and Vienna Lager, or limited releases that change throughout the year.

Walking distance from Harborfront Inn: 6 minutes

Day 2

10AM: Sterlington Commons Delicatessen

For a casual egg sandwich, pancakes, or French toast breakfast, head to Sterlington Commons Delicatessen near the Shelter Island ferry. The breakfast special includes coffee, tea or orange juice.

Walking distance from Harborfront Inn: 1 minute

1PM: Greenport Farmers Market

Swing by the Greenport Farmers Market for Long Island’s best locally grown food. Farmers and fishermen alike sell the best fruits, vegetables, jerky, ice cream, and desserts.

Walking distance from Harborfront Inn: 4 minutes

4PM: Shelter Island

Take the ferry to Shelter Island, an island community with rural character and country charm. Enjoy beaches, swimming, fishing, cycling, golf, and hiking.

Distance from Harborfront Inn: 15 minutes via ferry

7PM: The Frisky Oyster

The eclectic menu at The Frisky Oyster includes Peconic Gold Oysters on the Shell, Tempura Soft Shell Crab, Grilled Lobster Quesadilla, Tuna Tartare, and Duck Confit Spring Rolls. Don’t miss the parmesan truffle fries, blustered shishito peppers, or the cocktail list.

Walking distance from Harborfront Inn: 3 minutes

Day 3

10AM: Aldo’s Coffee Co.

Since 1987, Aldo’s Coffee Co. has been the go-to European-style café in Greenport. Head here for a cup of coffee, and for Aldo’s famous biscotti and scones.

Walking distance from Harborfront Inn: 2 minutes

1PM: Kontokosta Winery

Set against the stunning backdrop of the Long Island Sound, Kontokosta Winery features the island’s only public tasting room. The 24-acre property, located atop a bluff with scenic views, offers a standout experience along with a red or white tasting flight. Perfect for summer, the 2014 Kontokosta Rosé won the “Double Gold, Best of Class” distinction in the 2015 New York Wine & Food Classic.

Driving distance from Harborfront Inn: 7 minutes

7PM: Claudio’s

Established in 1870, Claudio’s serves up lobster, seafood and steak in a National Historic Landmark. Enjoy the water views with a selection from the wine list or cocktail menu.

Walking distance from Harborfront Inn: 4 minutes

Day 4

10AM: Complimentary Continental Breakfast at the Harborfront Inn

11AM: Check Out at Harborfront Inn