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.

Early Morning

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. 

Because the Woodstock Foundation owns and manages both the farm and the hotel, guests of the inn gain free entry to the working dairy farm and “museum of Vermont’s rural past.” The best tip we got from visitor information was to watch the 30-minute film “A Place in the Land” at the visitor center’s theater before doing anything else on the property. This Academy Award-nominated documentary explains the history of the farm, the park and Woodstock itself, leaving the viewer with an appreciation of the conservation stewardship of the three families behind it all.

Highlights at Billings Farm include the museum and the 1890 farm manager’s house, full of modest antique furnishings, where you can go on a self-guided tour. There are also gentle walking paths, animal barns, farm-life exhibits, a gift shop and a learning kitchen, which offers classes and demonstrations. If you are there in August or September, be sure to visit the Sunflower House. At 20,000 square feet, it is the largest sunflower house in the country, and it showcases many varieties during the five-to-six-week growing cycle.