This Cozy New England Town Only 100 Miles From NYC Is One of America’s Best Winter Weekend Getaways

Winter in Litchfield, Connecticut , isn’t about rushing from place to place—it’s about slowing down, pulling your sweater tighter, and letting the snow-coated streets do the talking. Just 100 miles from Manhattan , this small New England town made Travel + Leisure’s list of America’s coziest winter escapes , and it’s rarely getting talked about — especially in New York circles. Snow-dusted Federal-style homes surround the historic Green, fireplaces glow through frosted windows, and even a quick stroll feels like stepping into a Hallmark movie—if Hallmark had a multi-million dollar wardrobe budget. High-fashion dairy & breakfast, alone, worth the drive ------------------------------------------------------ You can’t discuss or even think about planning a trip to Litchfield without mentioning Arethusa Farm . The dairy here is run by former executives from Manolo Blahnik, the high-end shoe brand, and they pamper their cows like VIPs—with showers, climate-controlled barns, and spotless living spaces. But the real draw you may be wondering? The “everything-made-from-scratch” glory of Arethusa a mano where there is world-class coffee, donuts that sell out by noon, and farm-fresh scoops . For the full experience, book a table at Arethusa al Tavolo , where Executive Chef Dan Magill executes farm-to-table meals with Michelin-level precision but the warmth of a neighborhood haunt. The real-life ‘Stars Hollow’ ---------------------------- The heart of Litchfield is the town’s massive snow-covered Green , anchored by the First Congregational Church—the most photographed white-steepled church in New England.. While nearby Washington Depot served as the technical inspiration for *Gilmore Girls*, Litchfield is where that vibe truly lives. Stroll the square, duck into Litchfield Books , or grab a flight of local spirits at Litchfield Distillery . Just down the road, Hickory Stick Bookshop delivers the quintessential literary moment where signed copies of bestsellers casually sit on the shelves because the authors live just a few woods over. Winter adventures that feel surreal ----------------------------------- Litchfield offers experiences you won’t find in guidebooks, and is one of the more thrilling New England adventures you can find relatively close to New York City. Ice sailing on Bantam Lake is otherworldly: sailboats on runners zip across frozen water at 60 mph, leaving frosty arcs behind them. Trails at the White Memorial Conservation Center stretch for 40 miles, with wooden boardwalks weaving over frozen marshes—perfect for snowshoeing or spotting bald eagles along the Housatonic . Topsmead State Forest and Mohawk Mountain are also region-famous destinations, which add sledding, skiing, and easy winter hikes to the mix. Where to stay & eat ------------------- * The Abner Hotel — The town’s newest crown jewel. Housed in the former 1888 courthouse, it’s a masterclass in “adaptive reuse.” Grab a drink at Verdict , their rooftop bar, for the best view of the town’s chimneys. * The Belden House – A stunning, ultra-exclusive 1795 B&B situated on North Street (the “Millionaire’s Row” of Litchfield) for those who want historic intimacy. * Litchfield Inn – A lovely colonial boutique hotel set at the foothills of the Berkshires — breakfast included, pet-friendly. * Marketplace Tavern: Located inside the old 1812 jailhouse . With its original stone walls and moody lighting, it’s the ultimate spot for a dark, cozy dinner. * West Street Grill & The Village Restaurant – Voted a top restaurant by Connecticut Magazine, this spot serves farm-to-table and hearty pub fare, ideal for warming up after a snowy stroll. Best time to visit ------------------ February is quite literally the sweet spot for Litchfield’s winter magic. Post-holiday crowds are long gone, the snow is at its deepest, and every fireplace is ready for out-of-state visitors! At only a 2 hour drive from NYC , the route is super approachable, and we highly recommend taking Route 7 for the final leg—covered bridges and icy river views make it a scenic opener that will set the vibe for what you’re about to experience. Source: https://secretnyc.co/litchfield-connecticut-coziest-small-town-in-us-winter-weekend-getaway-travel-and-leisure/