Long Island might be famous for its beaches, but winter is a magical time to explore cozy escapes, indulge in seasonal activities, and discover the beauty of the island during the colder months. Whether you're planning a romantic retreat or a family adventure, here are the best winter weekend getaway ideas on Long Island to warm your soul and brighten your season.
Charming Escape in Greenport
Greenport’s cozy charm and festive atmosphere make it a perfect winter retreat for couples, families, or solo travelers looking for a seasonal escape.
Must-Do Activities:
Stay: Choose from The Harborfront Inn for waterfront luxury, The Menhaden for boutique elegance, or Sound View Greenport for cozy accommodations with sweeping winter views.
Explore: Wander through the quaint streets of Greenport illuminated by festive lights, visit Mitchell Park for ice skating with harbor views, and enjoy the iconic carousel for a touch of nostalgia.
Dine: Warm up with a bowl of chowder at Noah’s, enjoy farm-to-table favorites by the fire at First and South, or savor handcrafted cocktails and hearty meals at American Beech.
Shop Local: Browse the unique shops and art galleries for holiday gifts and local treasures, or stop by the winter farmers’ market for fresh seasonal goodies.
Greenport’s blend of holiday magic, winter activities, and cozy dining options makes it an irresistible destination for a charming winter escape.
Winter Wonderland in Montauk
Montauk in winter offers peaceful solitude with stunning coastal beauty, making it the perfect destination to recharge and reconnect.
Must-Do Activities:
Stay: Choose from luxurious Gurney’s Montauk Resort with oceanfront views and a year-round heated pool, the boutique charm of Hero Beach Club, or the historic elegance of Montauk Manor.
Play: Stroll along quiet beaches like Ditch Plains or Gin Beach, hike the snowy trails of Hither Woods Preserve or Camp Hero State Park, and visit the Montauk Point Lighthouse for breathtaking winter vistas.
Unwind: Pamper yourself with a massage or facial at Gurney’s Seawater Spa, relax in a private spa cabana, or savor a warm bowl of clam chowder at Gosman’s Dock. Don’t forget to sip mulled wine or gourmet hot chocolate by the fire for the ultimate cozy experience.
Montauk’s tranquil winter charm is the perfect escape for nature lovers and those seeking a serene retreat.
Wine and Warmth in the North Fork
Winter is the perfect time to savor the North Fork’s cozy charm and indulge in uncrowded wine country experiences.
Must-Do Activities:
Stay: Cozy up at Sound View Greenport for stunning waterfront views, or enjoy boutique-style accommodations at The Menhaden or the Harborfront Inn.
Taste: Sip mulled wine or indulge in wine-and-chocolate pairings at renowned vineyards like Kontokosta Winery, Bedell Cellars, or Pindar Vineyards.
Explore: Browse festive holiday markets, visit local farms for fresh winter produce, or pick up unique gifts from Greenport’s artisanal shops.
Unwind: Enjoy a fireside tasting at a winery or treat yourself to a hearty farm-to-table meal at a local favorite like Noah’s.
The North Fork’s serene winter atmosphere makes it a dreamy destination for wine lovers and holiday magic seekers alike.
Historic Huntington Holiday
Huntington Village becomes a magical winter wonderland, blending vibrant culture, seasonal charm, and festive experiences for a perfect holiday escape.
Must-Do Activities:
Stay: Feel like royalty at Oheka Castle, surrounded by a snow-dusted landscape, or opt for the elegant Inn at Fox Hollow for cozy luxury nearby.
Explore: Visit the Heckscher Museum of Art for a cultural immersion, shop for unique finds in Huntington’s boutique-filled streets, or take a snowy stroll through Heckscher Park. Don’t miss the Huntington Holiday Spectacular, featuring dazzling light displays and seasonal festivities that light up the village with holiday cheer.
Dine: Enjoy a fireside dinner at Prime with stunning waterfront views or warm up with hearty comfort food and cocktails at The Shed. Treat yourself to a sweet stop at Kerber’s Farm for hot cocoa and freshly baked pies.
Unwind: End your day with a live show at The Paramount or soak in the holiday ambiance with festive lights and decorations throughout the village.
Huntington’s mix of history, culture, and holiday magic makes it the ideal winter getaway for couples, families, and festive explorers alike.
Festive Family Fun in Port Jefferson
Port Jefferson transforms into a charming winter wonderland with festive activities, making it the perfect destination for family fun this season.
Must-Do Activities:
Stay: Cozy up at Danfords Hotel & Marina, where waterfront views and charming accommodations set the scene for a magical holiday getaway.
Experience: Step back in time at the Dickens Festival in December, when the village comes alive with Victorian carolers, horse-drawn carriages, and costumed characters bringing holiday cheer. Don’t miss ice skating at the Village Center or a scenic winter stroll along the harbor.
Dine: Warm up with a cup of cocoa or tea at Toast Coffeehouse, enjoy fresh seafood at The Steam Room, savor Mexican-inspired dishes at Barito, or treat the family to holiday-themed sweets from Roger’s Frigate.
Explore: Browse unique shops along Main Street for holiday gifts, and check out local art and crafts at the Port Jefferson Winter Market.
Port Jefferson’s holiday charm, festive activities, and diverse dining options make it a perfect winter escape for families seeking seasonal fun and unforgettable moments.
Cozy Retreat on Shelter Island
Shelter Island’s serene winter landscape is the ultimate escape for unplugging, recharging, and enjoying peaceful solitude.
Must-Do Activities:
Stay: Choose from the cozy, vintage-inspired charm of The Chequit Inn, the elegant waterfront accommodations at the Ram’s Head Inn, or the boutique comfort of Seven on Shelter Island for a luxurious retreat.
Explore: Wander through the snowy trails of Mashomack Preserve, one of Long Island’s most beautiful nature sanctuaries, or birdwatch along the quiet, tranquil shoreline for a glimpse of winter wildlife.
Relax: Curl up by the fireplace at your inn with a good book and a steaming mug of cocoa, or enjoy a soothing yoga session offered at some local retreats.
Unwind: Treat yourself to a cozy meal of locally inspired dishes at the Ram’s Head Inn or indulge in baked goods and warm drinks from Marie Eiffel Market.
With its peaceful charm, breathtaking winter scenery, and cozy accommodations, Shelter Island is the perfect spot for a relaxing and restorative winter getaway.
Winter Activity Highlights Across Long Island:
Holiday Light Displays: Visit the Magic of Light at Jones Beah or one of the many lighting events across Long Island
Indoor Fun: Enjoy a day at the Long Island Aquarium in Riverhead or catch a live performance at The Paramount in Huntington.
Seasonal Treats: Visit a local bakery for warm apple cider donuts or festive hot chocolate.
Tips for Planning Your Winter Weekend Getaway:
Pack Warm Layers: The Long Island winter chill calls for cozy coats, scarves, and gloves.
Book Early: Inns and boutique hotels often fill up during the holiday season.
Embrace the Off-Season: Many destinations are quieter in winter, offering a more intimate experience.