Woodstock, Vermont

 Mountain Views and So Much More

When most people think of Woodstock, that famous music festival probably comes to mind. Unless, of course, they’ve been to Vermont. 

Anyone who has been fortunate enough to visit or stay at “the other Woodstock” won’t soon forget it. A quaintly scenic locale, located on the banks of the Ottauquechee River and the base of Green Mountains, it’s brimming with charm. 

Rustic yet also quite sophisticated, the “Shire Town of Windsor County” was named “The Prettiest Small Town in America” by the Ladies’ Home Journal and has been lauded as one of the “Great Places in America” by the American Planning Association. Home to artists and artisans, shopkeepers and skiers, the 3,000-strong village was chartered in 1761 and owes much of its appeal to painstaking preservation of its 19th Century architecture, a wonderfully scenic ridgeline, and pleasing rural surroundings.  

Adding to the backdrop of breathtaking mountain scape and picturesque covered bridges, the totally wireless village is dotted with gorgeous Georgian-, Federal-, and Greek Revival-style homes and buildings, all clustered around a central square, called the “Green.” The wealthy tourist town, curated and cared for by members of the Rockefeller family for generations, also offers plenty of shopping, dining, cultural stimulation, and a multitude of outdoor activities. It’s also not too far from neighboring resort areas such as Killington, Ludlow, and the Quechee Gorge.

A year-round destination that’s sure to inspire no matter the season, the idyllic country village really shines during the winter months. Colder season events include a Wassail weekend in December, plus skiing, sledding, snowshoeing, fat tire biking, snowmobiling, ice skating, ice fishing, ice climbing and sleigh rides as long as the weather allows.

The Woodstock Inn

Fun facts: 

• Broadway star Gwen Verdon and actress Daphne Zuniga are both from Woodstock. 

• The Chevy Chase movie Funny Farm was filmed here, as were a handful of others. 

• The Academy Award-nominated film A Place in the Land highlights the community and its sustainable farm.

Places of interest: 

• The Suicide Six Downhill Ski Area, which is a 10-minute drive from the village Green. The site boasts the use of America’s first ski-tow rope, which was powered by a Ford Model T engine. A family-friendly resort, it offers a mix of terrain for beginner, intermediate and advanced skiers on three lifts and 24 trails. 

• The Billings Farm and Museum, a 150-year-old working dairy farm and museum. Formerly owned by Laurance and Mary Rockefeller, née Billings, the landmark farm is host to cows, sheep, horses, oxen, and chickens. There’s always something to do there, from farm-to-table programs to historical exhibits to a blowout Harvest Weekend every October. 

• The Marsh Billings Rockefeller National Historic Park, a 550-acre forest park that offers miles of trails for hiking, cross-country skiing, and snowshoeing. Also passed down from the Rockefeller family, the scenic park — the only such national park located wholly in the state of Vermont — draws focus on conservation, land stewardship and the understanding of the forested landscape. 

• The Middle Bridge, an all-peg constructed wooden bridge that spans the Ottauquechee River. One of three in the area, it offers stunning views and is a great place to snap some photos.

• The Paul Revere Church Bells, manufactured at the Massachusetts foundry owned by America’s most famous Midnight Rider. There are six of them in Woodstock — spread throughout the town: at the Congregational Church, the Woodstock Inn, the Masonic Temple, the St. James Episcopal Church, the North Universalist Chapel Society, and the Woodstock Country Club. 

• The Norman Williams Public Library, located in a grand circa-1883 stone building, the library is a cornerstone of the community. Located on the “Green,” it’s host to more than 400 public programs a year. 

Upcoming Annual Events for 2022:

• The Covered Bridge Half Marathon in June

• July 4 Patriotic Events for Independence Day

• The 12th annual Taste of Woodstock in the Summer

• The Woodstock Art Festival in September

• The Fall Hunter Jumper Show in September

• The 50th annual Apples and Craft Fair in October

• Leaf Peeping in October and November

• The 37th annual Wassail Weekend in December