Woodstock has been named the prettiest small town in America. And the most beautiful. And the most charming. Having recently spent a few days there, I can see why. On our latest Vermont visit, we stayed at the 142-room Woodstock Inn & Resort, which is situated across from the village green in the center of town. The hotel owes a debt of gratitude to Laurance Rockefeller, who rebuilt the storied hotel and reopened it in 1970. In fact, he and his wife, Mary, left a substantial mark on the whole town, investing in historic preservation and establishing a museum and working farm on property once owned by Frederick Billings, Mary’s grandfather. They also donated land and their family home to create Marsh-Billings-Rockefeller National Historic Park.
On the day we arrived, the vibrant Market on the Green was taking place — as it does every Wednesday, June to October. Full of artists, farmers, cheesemakers and brewmasters, it was a wonderful introduction to Woodstock. This idyllic New England town has plenty of riches to share; here’s how to spend one perfect day there.
There’s a lot to do today, so wake up early and request a patio table at the Woodstock Inn’s Red Rooster restaurant. Enjoy a leisurely breakfast while looking out over the manicured South Lawn. Then get a jump on other visitors and head to Billings Farm & Museum (69 Old River Road), just half a mile away. You can drive and park there, walk or request a shuttle from the hotel.