About Woodstock, Vermont
Recognized as one of the most iconic New England towns in the region
Woodstock, Vermont was first chartered in 1761, fifteen years before the United States signed the Declaration of Independence. It became the shire town, or county seat, twenty-five years later, in 1786.
As a shire town with the county's courthouse and jail, Woodstock attracted a host of professional people and entrepreneurs. Within a short period of time, Woodstock became a commercial and manufacturing center with shops and mills that produced everything from woolen products to linseed oil.
The Woodstock Village Historic District, encompassing the town center, was listed on the National Register of Historic Places in 1973. The district features a variety of architectural styles, including Federal, Greek Revival, and Queen Anne, reflecting the town's development over time, according to a travel guide.
For over 200 years, the focal point of Woodstock Village has been the famed site of what is now known as the Woodstock Inn. The original structure was built in 1792, and in 1874 tourists were inspired to flock to the area via "The Woodstock Car" - a rail car that departed nightly from Grand Central Station in New York City.
There are four main historic covered bridges near Woodstock: Lincoln Covered Bridge, Middle Covered Bridge, Taftsville Covered Bridge, and Quechee Covered Bridge. The town gets into the Christmas season during the very popular annual Wassail Weekend.
The town is home to a variety of beautiful country inns, hotels, motels, and casual to elegant dining venues. You can tour Main Street and learn about ghosts of the past and the history of the quaint town. Informational tours let you in on old Woodstock folklore secrets and mystery. You’ll see horse-drawn buggies, carolers, and many of the town’s historic homes and farms.
Woodstock is renowned for its rich mix of Georgian and Federal-style architecture and its scenic setting beside Mt. Tom. Winding roads trace the Ottauquechee River, and four picturesque covered bridges dot the landscape.
Today, Woodstock continues to honor its heritage through a vibrant artisan culture and a strong tradition of tourism. The town celebrates its classic American charm with outdoor recreation, boutique shopping, and farm-fresh dining that highlight the beauty of its rural surroundings.
It remains a thriving community of artists, makers, and local tradespeople, attracting visitors who come to explore its many historic treasures. Whether wandering its scenic streets or discovering its creative spirit, every corner of Woodstock offers a glimpse into the town’s enduring legacy.