As Winter arrives, a magical transformation takes place in upstate New York. The landscapes surrounding East Chatham become stunning, showcasing nature's beauty under a blanket of snow. The Hudson Valley and the Berkshires invite urban dwellers to leave their busy routines behind and experience the wonders of the great outdoors. From exciting outdoor activities to cozy hideaways, this region offers an unforgettable winter experience just a few hours from New York City.
Discover the best Winter activities in East Chatham
For thrill-seekers, East Chatham and its surroundings are packed with winter adventures. Skiing and snowboarding are top attractions in the Berkshires, with the Catamount Ski Area only a short drive away. This location has 35 trails catering to various skill levels, making it ideal for everyone from enthusiastic beginners to seasoned experts. With a vertical drop of over 1,000 feet and stunning vistas, Catamount stands out as one of the best ski spots in the region.
Prefer a more family friendly pace? Try Bousquet Mountain. This hidden gem features trails that meander through beautiful woodlands, offering perfect opportunities to connect with nature. Bousquet also offers multiple levels of ski and boarding slopes as well as classes.
Want to stay on site? We offer complimentary snow shoes (first come, first serve) and have our very own trail on property. Ask the innkeepers to set you up and do a little exploring of our grounds.

Wine Tasting in Cozy Wineries
After a day full of outdoor adventures, why not unwind with a glass of wine? The Hudson Valley is home to numerous wineries that produce exceptional wines with locally grown grapes. Many of these vineyards offer winter tasting rooms, providing guests the chance to sample a range of aromatic reds, crisp whites, and sweet dessert wines in a warm, welcoming atmosphere.
Some wineries host special seasonal events, pairing wines with hearty winter fare, which adds an extra layer to your tasting experience. Imagine sipping on a velvety cabernet while admiring the view of snow-covered vineyards—it’s a sublime way to end your day.
Our neighbors at The Hudson Chatham Winery offer tastings Thursdays - Sundays through a curated flight of their portfolio. They also have their own apiary and 40 French Maran chickens, which are delightful to witness!

Charming Towns to Explore
What’s a winter adventure without a little local exploration? East Chatham is surrounded by charming towns worth visiting. Take a scenic drive to Chatham and discover its inviting shops and eateries. Don't miss Chatham Brewing Company, where you can sample locally crafted beers—a delightful way to relax after a day of fun.
Make sure to visit the historic town of Hudson, known for its unique thrift stores and antique shops. Wandering through quaint shops can feel like diving into a treasure hunt, allowing you to soak in the small-town charm and vibrant community spirit. One of our favorite haunts is the Antique Warehouse.
Skating and Sliding Escapades
Ice skating is a winter staple that brings joy to all ages. Head to Lake Taghkanic State Park, where you can skate on a frozen pond surrounded by beautiful winter scenery. Bring friends or family, grab some hot cider, and enjoy the nostalgic experience of skating outdoors. (BYO skates, available if conditions permitting)
If you're looking for more excitement, sledding or tubing at local hills can provide hours of entertainment. With various slopes offering different levels of thrill, it’s a fantastic way to create lasting memories with loved ones.
Your Winter Getaway Awaits
As winter dresses the landscapes near East Chatham, New York, this region becomes a magical wonderland awaiting your exploration. From exhilarating outdoor activities to cozy indoor retreats, the Hudson Valley and the Berkshires invite you to relish the charm of the season and create unforgettable experiences.
Whether you crave adrenaline on the slopes or prefer quiet moments spent sipping wine by a fireplace, there's something special for everyone in this winter escape. Gather your friends, pack your bags, and unveil the hidden wonders of winter in upstate New York. Your adventure is waiting, promising to be a remarkable journey! Check our availability and book here. Thanks for reading!

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