Discover the Charm of Woodstock VT: A Family Legacy and Timeless Destination

A Family Legacy in Woodstock VT

In the summer of 1977, a young Rick Higgerson embarked on a journey that would forever shape his family’s connection to New England. Traveling from Hong Kong, where his family then lived, Rick arrived in Fairlee, Vermont to attend Camp Lanakila on Lake Morey. Meanwhile, a spontaneous detour led his parents through the charming village of Woodstock VT. Struck by its timeless appeal, Rick’s mother, Nancy, asked to stop the car. She stepped into a local real estate office and, on impulse, rented a quaint cottage on Togo Hill for the summer.

That serendipitous decision sparked a lifelong bond between the Higgerson family and the Woodstock area—one that continues to this day.

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Woodstock VT: Where History and Charm Converge

Declared one of the prettiest small towns in America by numerous publications since 1986, Woodstock’s rich heritage as a destination dates back far earlier. Chartered in 1761—15 years before the Declaration of Independence—the town quickly flourished as the Shire Town of Windsor County. Early settlers built stately homes and commercial blocks, many of which still stand today as iconic landmarks on Main Street.

This deep-rooted architectural and agricultural history sets Woodstock apart, drawing visitors and new residents who value authenticity and character.

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Modern Appeal with a Deep Sense of Place

Woodstock VT has preserved its historic identity while embracing forward-thinking values. The The Marsh-Billings-Rockefeller National Historical Park leads conversations on conservation and land stewardship in America, while nearby Billings Farm & Museum maintains a working dairy farm and a beautifully preserved 1890s farmhouse.

As former residents of South Pomfret for over a decade, our own Higgerson family spent countless hours with our children on the trails of Mount Tom and among the pastures of Billings Farm. These treasured landscapes are part of daily life here.

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A Vibrant Community Year-Round

Whether you’re strolling through Woodstock’s charming village center with its boutique shops and locally owned restaurants, or enjoying live music and films courtesy of Pentangle Arts, there’s a constant heartbeat of cultural activity.

Outdoor enthusiasts are spoiled for choice: hiking, biking, fishing, and golf in the warmer months transition to downhill, Nordic, and backcountry skiing, plus snowshoeing, in the winter. No matter the season, Woodstock offers something for everyone.

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Real Estate in Woodstock, VT and Beyond

From storybook village homes to sprawling country estates, Woodstock presents a diverse range of real estate opportunities. Whether you’re searching for a primary residence to call home or a seasonal escape, Higgerson & Company brings unmatched local expertise in Woodstock, VT, Hanover, NH, and the many scenic communities that surround them.

If you’re dreaming of a life anchored in beauty, history, and community, we would be honored to help you find your place here.

Let’s talk. Your Vermont story starts now.