Long Island Winter, You’re Hard to Beat

Though I grew up on Long Island’s North Shore, I now live in Southern California where it’s 75 degrees and sunny nearly 365 days a year. It’s hard to imagine missing winter, and yet, I do. There are certain things about a cozy, bundled up Long Island winter that you just can’t get elsewhere in the country. From sipping wine on a cooled-down vineyard to bundling up to watch lit boats snake down the island’s harbors, there’s a reason I find myself booking a plane ticket back each year once the weather cools.

Off-season on the North and South Forks


There’s something especially cozy about hunkering down in a summer destination during the off-season. The winter options seem endless. I remember settling into a table at North Fork Table and Inn while also trying to snag a reservation at Nick & Toni’s. Of course there’s always touring the still-buzzing wineries, checking out the decked-out Montauk Lighthouse and taking in the brisk ocean air on a cold weather walk. Dare I say winter is one of the most enchanting times to be in these summer towns?

Boat parades

Long Island is home to at least three over-the-top boat parades during the holiday season taking place in Huntington, Freeport and Patchogue. The harbors and bays are lined with families and friends huddled together to watch the spectacle motor show. There’s hardly a better way to usher in the holiday season when you live on an island.

Holiday light displays

Girl Scouts of Suffolk County

image: facebook.com/gssc68

As a kid, one of my family’s favorite pastimes was to drive all over Long Island to catch the different light displays. In particular, we loved Bayville Winter Wonderland, which has everything from a soda shop to ice skating. The two-mile long Girl Scouts of Suffolk County holiday light show at Smith Point County Park was another favorite, especially since it’s one of the largest light shows on the island.

Holiday tours at the Vanderbilt Mansion

One of Long Island’s greatest historical treasures is in the small hamlet of Centerport where William K. Vanderbilt built his sprawling Spanish-style home overlooking Northport Harbor. The estate is gussied up and outfitted for the holidays, giving everyday Long Islanders a glimpse of what celebrating the season Gatsby-style must have been like.

Outdoor ice skating

Tanger Outlets Deer Park Ice Rink

image: facebook.com/tangericerink

Move over, Rockefeller Center! There are plenty of places to enjoy ice skating outdoors without having to trek into the city. Syosset-Woodbury Community Park, Christopher Morley Park, Mitchell Park Rink and Tanger Outlets in Deer Park all have outdoor skating facilities that are family-friendly.

Long Island’s delicious restaurants

When the temperatures drop, many Islanders head indoors for meals and memories they’ll remember. Whether sampling one of the buzzed-about restaurants in hot spots like Huntington, Babylon and Patchogue, or simply tucking into a familiar booth at a neighborhood favorite, I miss the excitement that comes with heading out for a good winter night on the island. Bonus points if there’s a fireplace roaring in the background.

Finding offbeat ways to enjoy the water

Port Jefferson, NY

image: facebook.com/portjeffny

It’s too cold to sunbathe on the beach, but there are still plenty of ways to connect with the water during winter on Long Island. Aside from watching the aforementioned boat parades, I loved going on seal tours through Hempstead Bay, watching friends undertake polar plunges and going for walks alongside the Long Island Sound at Caumsett State Park.