Winter Weekend on Long Island: Fire, Ice, and Everything Nice


Winter on Long Island is not all about shoveling driveways and dodging potholes that could pass for Olympic ski jumps. Oh no, we have much more to offer: cozy fire sides, glistening ice-skating rinks, and enough delicious food and wine to keep even the fussiest Long Islander happy.

Looking for the perfect way to shake off those winter blues? Well, you are right there, because we have planned your weekend itinerary full of charm and adventure, with a pinch of sarcasm to keep things interesting.


Friday Evening: Firelight and Fine Dining

Let's ease into the weekend, Long Island style: with good food and cozy vibes. Check into a charming spot like The Baker House 1650 in East Hampton. Their fireplaces are so inviting you might just start wondering if you're starring in your own Hallmark movie.


Dinner at The North Fork Table & Inn: its menu reads like a love letter to all things local. Braised short ribs, when in season, provide the sort of tender hug the soul requires in wintertime. A glass of wine will further convince one winter may not be as terrible an invention as generally touted.


Saturday Morning: Ice, Ice Baby


Wake up, have a cup of coffee, and get ready to enjoy the cold winter air. Start your day at The Rinx at Harbor front Park in Port Jefferson. Skating on this picturesque rink with the views of the harbor? It's #Instagold. Just don't fall-you'll never hear the end of it.

Not your scene? Channel your inner Arctic explorer at Caleb Smith State Park Preserve in Smithtown. Snowshoeing and cross-country skiing get the ol' heartbeat up while you pretend you're way more outdoorsy than you actually are.


Saturday Afternoon: Sip and Savor


Now that you've earned it, be off to the North Fork for a little wine tasting. Obviously, this is what you've been waiting for. At Bedell Cellars and Macari Vineyards, the hosts are warm and the mulled wine, well, even warmer. Kick back, chill, and let those gorgeous vineyard views remind you why you love it here-even in January.

Stop for lunch at Love Lane Kitchen in Mattituck. Their homemade chili will warm you up from the inside out, and their artisanal sandwiches are the real deal. Plus, Love Lane itself is so charming you might start checking Zillow listings.


Saturday Evening: Fireside Vibes


When the day cools down, find yourself a roaring fire. The American Hotel in Sag Harbor is your spot, complete with old-world charm, great cocktails, and fireplaces galore. You'll feel like you're from another era. Pro tip: Bring a book or strike up a conversation about local history to impress your friends.


Sunday Morning: Brunch Like a Boss


A Long Island weekend without brunch? Not on our watch. Get to Toast Coffeehouse in Patchogue or Port Jefferson for a morning spread that will last you all day. S'mores French toast? Yes, please. Want savory? Their frittatas are famous.


Afterwards, meander through the boutiques of Cold Spring Harbor or Greenport. These villages are ideal to pick up unique finds. Bonus points if you snag a locally made candle to keep that cozy vibe going back home.


Sunday Afternoon: Sweet Endings


Cap off your weekend on a quite literal sweet note: swing by North Fork Chocolate Company for some handcrafted truffles. Unless you are feeling ambitious-and up for an outing to Garden City's Cradle of Aviation Museum-where it is truly not every day you have the chance to learn about space exploration with hot cocoa in hand. 


Why Long Island in Winter? 

The balance of a Long Island winter weekend is appropriate, like a perfect cocktail. You'd find some fun in adventure and indulgence amidst charm. For whatever you enjoy doing-skating, sipping, or just taking in the view-all are welcome, which means you too.

With its perfect mix of charm, adventure, and indulgence, Long Island isn’t just a weekend destination—it’s a place to call home. Whether you're looking to upsize, downsize, or relocate to the area, I’m here to help you find the cozy retreat of your dreams.

📞 Call me at 516-984-3286 or 📧 email Dean@TheBeaconTeam.com today to get started.

Or visit www.TheBeaconTeam.com to explore Long Island's amazing homes and vibrant communities.

Let’s find your perfect home base for every season—because life’s better when you’re living it Long Island style.