Woodstock Way Hotel
An Upstate Immersion
Woodstock, NY is a living legend — and a hub of activity. We encourage you to make your time here uniquely your own, but we hope our itineraries will spark inspiration down the path of exploration and wanderlust.
36 Hours in Woodstock
Morning
With the rush of the Woodstock Waterfall as your only alarm clock, roll out of bed and head to the Tannery to fuel up on coffee and pastries. Spend a little time on the Waterfall Terrace, take a short walk to a yoga class, or set out for a hike along the Comeau Trail before heading into town.
Afternoon
Shop, wander, and while away the day in historic Woodstock. Check out the local shops and stop in at our hotel bar called Small Talk in the center of town.
Evening
Shower, nap, then take in the waterfall views from your private balcony. Walk over to Silvia’s for dinner, then ramble over for live music at The Colony or Levon’s. Late night drinks at Early Terrible are always a good idea before heading back to Woodstock Way — then sleep, sleep more, and repeat.
Plan Your Trip
This town is a true gem. Plan your trip with the help of our favorite places to dine, shop, heal, hike, swim, adventure, and listen.
Explore Woodstock