Living in Woodstock, Vermont

In the summer of 1977, a young Rick Higgerson traveled from Hong Kong, where his family lived at the time, to Fairlee, Vermont where he would spend a few weeks at Camp Lanakila on Lake Morey. As luck would have it, a scenic detour found his parents passing through Woodstock. Struck by the charm of the village, Rick’s mother, Nancy, asked for the car to be stopped, hurried into the local real estate agency, and promptly rented a magical cottage on Togo Hill for the summer. Little did she know that this impulsive decision would lead to a lifetime connection to Woodstock and the surrounding area.

Though declared by multiple press outlets, beginning in 1986 and continuing to the present day, to be one of the prettiest small towns in America, Woodstock’s history as a destination in Vermont goes much farther back. The village was established in 1761, making it older than the Declaration of Independence itself by over 15 years. Serving as the Shire Town of Windsor County, Woodstock quickly became a bustling center for Vermont commerce and law, with the county court located on the Village Green, and early entrepreneurs seizing the opportunities the land had to offer. Woodstock’s stature saw the building of several significant historic homes and commercial blocks on Main Street which stand as testaments to the town’s rich architectural and agricultural heritage.

Today, the town continues to honor its past while embracing modern trends. Positioned at the forefront of inquiry into the evolving nature of conservation and land stewardship in America are Woodstock’s  Marsh-Billings-Rockefeller National Historical Park and the working dairy farm and 1890 farmhouse at Billings Farm & Museum. The farm and the trails on Mount Tom are beloved by local children and parents alike; we spent countless hours with our little Higgersons exploring both during the 10 years we lived in South Pomfret. The village’s charming historic center offers boutique shopping and fine dining at small, locally owned businesses. Year-round outdoor adventures abound – hiking, mountain biking, fishing, and golf before the snow, and alpine, Nordic and back country skiing, and snowshoeing when snow is on the ground. And Pentangle Arts entertains locals with current movies and live music performances.

From cozy village homes to country farms and estates, Woodstock offers a diverse range of real estate options for those looking to make this picturesque town their home. If you are considering a new home in the area or a vacation property, Higgerson and Company are your real estate experts in Woodstock, VT, Hanover, NH, and the constellation of wonderful towns that surround us. Please be in touch and let us guide you home.