Karen Lee at Sang Lee Farms

Sound View Winter Explorer

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Adventure Like A Local

We’re thrilled to share the best of the North Fork in winter from charming towns to farms and vineyards. Seasonally inspired and locally driven, our itineraries are a blueprint for your ultimate North Fork getaway. Find inspiration to start planning your trip or let us take care of the details for you. Browse our itineraries below and start planning your stay today. Questions? Just ask.

The Village

You’ve escaped the city for a few days and it’s time to soak up all the small town feels. Make the village of Greenport your home base. Get your morning going with small-batch roasted, organic coffee at Aldo’s Café, and since you’re on vacation, spring for the Italian biscotti, a local legend around here. Skate over to Mitchell Park’s outdoor ice-skating rink overlooking Greenport Harbor for a quintessential winter experience. If the weather’s severe, keep rolling—over to the newly renovated, year-round Roller-skating Rink in the American Legion.

When you’ve worked up an appetite, sip into Little Creek Oysters to learn to shuck your own while sipping the local beer on draft.
Explore Greenport Village’s new indoor farmer’s market, unique galleries, and local boutiques. Some of our favorites include The Weathered Barn and Preston’s Marine shop. Cap things off with a cocktail at Brix & Rye’s award-winning bar before ending the night with dinner in Stirling Square. You can’t go wrong with 1943 Pizza bar or American Beech.

Local Tip: Pass the popcorn: The Manhattan Film Institute is screening two free movies (classic films and family favorites) every Saturday night from December to May at the historic Greenport Theatre. (https://www.manhattanfilminstitute.com/saturdayfilmseries)

Town & Country

Small towns, big charm—visit some of our favorite neighborhoods just beyond our stretch of the Sound. First thing’s first: start your day with a hearty brunch and a (Sound) view at The Halyard Restaurant. Hop in the car and head east to the historic hamlet of Orient, on the eastern tip of Long Island. Stop off for some homemade chocolates at The Candy Man. Stroll down Village Lane and visit shops along the way, and don’t miss the Oysterponds Historical Society’s display of local relics dating back to the 17th century. While you’re here, visit Orient Beach State Park, dotted with four lighthouses. Sit back and admire the coast line and keep an eye out for rare birds.

Head back west to Peconic Lane, and ask yourself, beer or wine? For beer, visit Greenport Harbor Brewery and for wine, the Winemaker Studio. Stop in at North Found & Co., an artfully curated vintage and antique general store, before heading out.

At Love Lane in Mattituck, indulge in warm, cheese fondue at The Village Cheese Shop, shop in various boutiques and gourmet food stores, including Lombardi’s Market and Roanoke Vineyards Wine Bar.

Local Tip: The town of Southold is another local gem. Sip a fresh-pressed juice from The Giving Room Yoga Studio & Juice Bar, or a fair-trade craft coffee from North Fork Roasting Company, and browse unique local shops. We love White Flower Farmhouse and About Food.

Farm & Vine

Our picks for the best ways to experience The Long Island Wine Trail (spoiler alert: it’s more than just wine). Rise and shine with a farm fresh brunch and tour of 8 Hands family farm, known for heritage breed livestock including Icelandic sheep.

Kick off your Long Island Wine Trail expedition at Macari Vineyards, a three-generation family winery in Mattituck known for top-end red blends. Move on to Lieb Cellars in Cutchogue to experience small production reserve wines and local live music on Saturdays.

Take a short break from tastings to gather farm fresh produce at one of the many local farms open year-round – our favorites are Deep Roots Farm, KK’s the Farm, and Sang Lee Farms.

Add a little sparkle to your day with a bubbly tasting at Sparkling Pointe, the only North Fork winery dedicated to the exclusive production of Méthode Champenoise Sparkling Wines. Savor a cozy dinner by the sea at The Halyard Restaurant, complete with a sommelier designed wine menu.

Porch overlooking water

Ready to see the North Fork?

Don’t escape winter, embrace it with 30% off your two-night stay, a warm winter welcome amenity, and a complimentary upgrade for Sunday – Wednesday arrivals.