Greenport, NY Getaway: How to Enjoy a Day on Long Island’s North Fork

Kontokosta Winery in Greenport, NY

Many people are familiar with the Hamptons and Montauk, but Greenport often flies under the radar. It did on mine until recently. Also located on Long Island, Greenport has the same beauty but a more laid-back vibe. It’s well-known for its wineries and farms, and unlike the Hamptons and Montauk, it has year-round appeal, offering something special during every season. That's why, when my dad came to visit this Fall, I decided to take us on a day trip to explore Greenport for the first time.

In this blog post, I share my experience as a Greenport, NY, first-timer and offer recommendations for anyone considering venturing to this charming coastal destination.

“In life, it’s not where you go it’s who you travel with.”
— Charles M. Schulz

Spend the Morning EXPLORING Greenport, NY

Even on a dreary day, Greenport didn’t disappoint. After a scenic 2 ½ hour drive from New York City, we arrived in downtown Greenport. If we hadn’t enjoyed our coffee on the drive up, I would’ve held out for one of the many charming coffee spots—in particular, Aldo’s Coffee Company.  Instead, we started our day walking through this one-square-mile village, stopping in antique shops and boutique stores and taking in the waterfront views.

Some of my favorite stops included:

  • Greenport Carousel in Mitchell Park is a vintage carousel with scenic views of the harbor. Unfortunately, it was under repair the day we visited, but I 100% would’ve taken a spin on it.

  • The Times Vintage has an eclectic atmosphere that evokes nostalgia, featuring a carefully selected mix of vintage clothing, records, jewelry, and furniture. It's been family-owned since 2013.

  • The Weathered Barn is a carefully curated boutique with a rustic barn feel showcasing a collection of home goods, vintage items, and local artisan crafts.

  • Burton's Bookstore is an independent bookstore located in the heart of Greenport known for its cozy atmosphere and welcoming vibe.

On my “next time I visit” list:

For more on Greenport, NY, visit greenportvillage.com

 

STOP IN KONTOKOSTA WINERY FOR A TASTING WITH A VIEW

Before leaving Greenport, be sure to visit Kontokosta Winery. It's one of the few wineries in the area with a waterfront view, located directly on the Long Island Sound. In addition, Kontokosta Winery is committed to sustainable practices, using environmentally friendly farming techniques. As you arrive, you'll pass through rows of vineyards that guide you to a sleek, modern barn that houses an elegant tasting room inside. Whether you enjoy your tasting indoors or out on the expansive lawn, you're guaranteed a breathtaking view.

 

MUST-VISIT STOPS ALONG NORTH FORK ON YOUR WAY BACK

On the drive back, there are plenty of great stops along the way. As we cruised down North Rd, we couldn’t resist pulling over near Hashamomuck Beach to take in the stunning views. Later, as we neared Mattituck, we made a stop at Lombardi’s Love Lane Market for one of the freshest pizzas I’ve ever had. Our last stop before hitting the highway was Waterdrinker North Fork, where we awed over all the pumpkins and mums before enjoying some live music at Long Island Farm Brewery.

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New York, North AmericaKaren GomezGreenport NY, Day TripsComment