Ah, finally the quiet of winter has arrived in the Catskills. The fresh snow storm in early January transformed the area into a winter wonderland – at least for a bit. But with or without snow, Woodstock is a wonderful place to visit in the winter.
Town is wonderfully peaceful and store owners and shopkeepers finally have time to really chat with visitors. A warm connection is made between locals and out-of-towners as everyone enjoys this relaxed pace. And the music and dining scene is still very lively.
For a perfect winter day in Woodstock, start with a drive through town and head up Meads Mountain Road for a morning hike at Overlook Mountain or head to Route 28 and park at any of the trailheads for a scenic walk beside the Ashokan Reservoir. (If downhill or cross-country skiing is more to your liking Belleayre is 30 minutes away and has some of the best snow-making in the Northeast since it became part of the state’s Olympic Development Authority.)
Overlook, at just under 5-miles round trip, has a steep ascent initially, but the views at the top are extra spectacular with winter’s bare trees offering a view that can include five states as well as the Hudson River. (It’s a good idea to bring along some crampons or hiking poles as the path can ice over.) Be sure to pack a scarf and/or hat as the open summit can get a bit blustery but you’ll definitely want to spend time enjoying the views, the fire tower and the abandoned hotel site.
The Ashokan Rail Trail is a flat, well-maintained path adjacent to the reservoir that provides New York City’s water supply. The first part of the 10-mile trail near Woodstock trailhead is protected with berms, so it’s not too windy. At the open area the view is so beautiful the wind is bearable. The nice part of this trail is it’s out and back, so simply go as far as you want.
After hiking head on into town for some deserved lunch. 
A visit to Yum Yum Noodle Bar, with its Asian specialties is sure to warm even the chilliest hiker. Or if its vegan and delicious you’re after, stop in at the Garden Café, to experience local food that is always lovingly crafted. Spend some afternoon time strolling along Tinker Street’s galleries and craft shops. Be sure to stop in at The Golden Notebook, Woodstock’s independent bookstore. You’ll be treated to a wonderful selection of best sellers as well as an artfully-curated selection about our town (called the Most Famous Small Town in America by National Geographic.) The store at the Woodstock Byrdcliffe Guild is the perfect spot to discover hand-crafted gifts and sculptures, and the rotating gallery displays are always unique.
You’ve worked hard today, and this is a getaway, so return to your room at the Woodstock Inn on the Millstream and give thanks you upgraded to a fireplace room. (If you’d like a personal room recommendation, always feel free to call or text the innkeeper at 845-663-8152.) It’s time to relax, crack open that new book and languish in an afternoon just reading and relaxing or sharing quiet time with a loved one.
For dinner plans, or to review the live music options in town, simply reach out to the innkeepers – all locals who loves to share their insider knowledge so guests can have the best experience possible in Woodstock. From specialized cuisine, and entertainment options that include world-famous musicians performing in intimate spaces to cutting-edge cinema or fun-loving karaoke, there is always an evening event to make your visit memorable.
After a solid night’s sleep, be sure to have a relaxing start to your day with our delicious continental breakfast. Enjoy the Inn’s grounds. Visit the stream. Marvel at the beauty of winter in the mountains. Embrace this time of quiet beauty.