Troutbeck is truly a four-season destination. Winter here means easy access to nearby family-friendly ski slopes, such as our closest, Mohawk Mountain (where snow making was invented!), which lends itself perfectly for an apres ski dinner at excellent restaurant newcomer the Pink House in West Cornwall. In Hillsdale, there's Catamount and in Great Barrington, Butternut Ski Resort, which is very close to our favorite Great Barrington cheese and natural wine shop, Rubiner's, and Prairie Whale where you should go for post-slopes dinner. Ski school for the kids and uphill "skinning" make for excellent pastimes, especially when a plentiful meal near one of Troutbeck's very own roaring fires is planned for after. Cross-country skiing and snow shoeing is even closer: on the Harlem Valley Rail Trail (access point is a 5 minute drive from Troutbeck) or at nearby Wethersfield, one of the region’s most distinguished estates and gardens, where hiking, snow showing or cross country skiing is available on their maintained trails for $10 per day. Our friends at nearby Elk Ravine Ranch offer tours of their exquisite Highland cattle and carriage rides (in snow too!) pulled by their beloved horses.

You’d be surprised what an appetite you can work up from a morning of skeet shooting at Orvis Sandanona. Nearby Millbrook School’s Bontecou ice rink is open to the public every Sunday December 8th – February 23rd) from 3:00 p.m. – 5:00 p.m., and is another excellent source of family fun, as is their Trevor Zoo, where rescued animals – including red pandas, grey wolves, otters and reptiles – are cared for by students.

If antiquing and meandering through charming villages is more your speed, Troutbeck is surrounded by those aplenty. Ten minutes from here, Millerton boasts antique shops and the stylish Nordic-chic brand, Westerlind in a historic former department store. Stay for an aperitivo at Willa, the new wine bar from former Troutbeck sous chef Daniel Meisner. Twenty minutes south, in Millbrook, there's antiquing galore, plus uber-chic shops Creel & Gow and Orangerie, a wonderful book and toy shop, Merritt Bookstore, and restaurant Canoe Hill.

Book a meal in exquisite Pine Plains restaurants Stissing House from chef Clare DeBoer or Champêtre from legendary restaurateurs Michel and Patricia Jean. Fifty minutes away, Hudson, with an unparalleled selection of antique shops and eateries (we love Feast & Floret and Café Mutton). In the other direction, Cornwall's new Pink House serves a delectable array of wines by the glass with thoughtful and excellent locally sourced fare. Further in that direction, Kent and Litchfield, CT offer both quaint and contemporary galleries, dining and shopping.

If you’re taking Metro North Railroad up from Grand Central Station to Wassaic (an 8 minutes drive from Troutbeck…taxis may be arranged ahead) and not you're planning on leaving the property, there’s much to do on site....

The Barns welcomes new wellbeing partner Wildsmith, who's curated fresh treatments and trained our staff on how to employ their extraordinary nature-driven products into wellness experiences based on our circadium rythms for maximum pleasure and effect.

Take advantage of our daily Wellness classes and book a session with our on-site personal trainer, which should of course be followed up by acupuncture and a massage from one of our lauded practitioners. Sound baths and astrology may also be organized, tailored to the centering you most crave.

There's so much to enjoy in winter in our corner of Dutchess County, on the border of Connecticut!

Wander the winter wilds this season at Troutbeck. Book a midweek stay now through March 31, 2025 and receive complimentary breakfast and a $50 hotel credit for every night booked.

Enter the code "WINTER" when booking online to delight in this offer.