How to Plan a Winter Weekend in Greenport

Even when temperatures dip below freezing, the charm of the North Fork doesn’t hibernate. Less traffic and fewer tourists in the winter make the season a prime time for a cold-weather escape, filled with shopping, dining and exploring 100 miles east of Manhattan. Bundle up for an ultimate winter weekend in Greenport.

Saturday

Start the day at Bruce & Son, a charming Main Street spot with an array of delicious breakfast and lunch options complemented by local beer and wine.

Lace up your skates at the waterfront ice rink at Mitchell Park, where Greenport Harbor provides the perfect backdrop to your triple axel. The rink is open daily until 5 PM, and on Friday nights until 9 PM. A $7 fee includes rentals.

Get toasty at Aldo’s Coffee Company, a small-batch coffee roaster and artisan baker in Greenport. The aroma of roasting coffee beans will beckon you to this local North Fork hangout, and once inside, you’ll find more than coffee on the menu. Try one of Aldo’s biscotti or scones, baked fresh daily onsite, or if you have kids in tow, don’t pass up a thick, rich hot chocolate.

Take a cup of coffee to go while exploring local shops in Greenport. The local, independent Burton’s Bookstore is among the standout shops in the village. At The Weathered Barn, a lifestyle boutique, more than half of the shop’s hand-made, artisanal home goods are created on premises.

To wind down your day, choose from one of the many amazing restaurants in Greenport, like The Frisky Oyster or Noah’s, or if dinner and a movie is more your style, grab a quick bite at 1943 Pizza or Lucharitos and head over to the Greenport Theatre for the Winter Movie Series, which includes some great classic films as well as showings for kids.

Sunday

Wake up at The Harborfront Inn and start the day with a complimentary continental breakfast and panoramic harbor views.

There are plenty of wineries on the North Fork, but Kontokosta Winery is one of the loveliest and just up the street from the inn. Perched atop the sweeping bluffs overlooking the Long Island Sound, Kontokota offers the unique opportunity to sample award-winning, handcrafted wines in the maritime climate from which they were created. The tasting room is open Sunday, Monday, Thursday and Friday from 11 AM to 5 PM and Saturday from 11 AM to 6 PM.