Сhristmas-card-perfect, small, and cosmopolitan, Woodstock earned its place in ski history when adventuresome locals hooked a long loop of rope to a Model T Ford engine at the base of Gilbert’s Hill in 1934, creating the first ski tow. While it still has some local skiing and is conveniently close to Killington and Okemo, today Woodstock is more famous for being the “prettiest small town in America,” according to the Ladies’ Home Journal. The title is due in part to the vast fortunes and concerted efforts of Laurance Rockefeller (grandson of Standard Oil magnate John D. Rockefeller Sr.) and his wife, Mary Billings.
The two married in 1934 and spent the next 60 years lavishing money and attention on the town, even burying the utility lines to maintain its pristine 19th-century feel. They donated 550 acres to create Vermont’s only national park, significant for being the first scientifically managed forest, with a 19th-century mansion sitting in its midst. They were also the force behind the Billings Farm & Museum, known for its blue-ribbon Jersey cows.
In 1969 Laurance and Mary built the town’s centerpiece, the rustic but genteel Woodstock Inn and Resort, on the village green. This 142-room Colonial Revival resort features top-drawer amenities like a 41,000-square-foot health and fitness center, horseback riding, and golf. The inn operates the Woodstock Ski Touring Center, with almost 40 miles of groomed cross-country trails, and the 23 downhill trails of the misleadingly named mountain, Suicide Six, which has a drop of just 650 vertical feet.
Woodstock was settled in 1765 by emigrants from southern New England who were attracted by its location on the Ottauquechee (AW-to-KWEE-chee) River. In the 19th century, the river powered woolen mills, one of which now houses the workshop of luxury glassware and pottery maker Simon Pearce. Find sustenance at the Mill at Quechee restaurant, known for its cheddar soup and Irish soda bread.
The nearby Quechee Gorge State Park is a dramatic 165-foot-high, mile-long gorge carved some 13,000 years ago by glaciers, with stunning aerial views looking down from the 1911 trestle bridge. While tour buses frequently stop here, you can easily escape them by hitting the trails that wind past pretty waterfalls down to the bottom of the gorge.
For a final dose of Vermont history, visit Plymouth Notch, the birthplace and boyhood home of President Calvin Coolidge, and a quiet hill town that is nearly unchanged since the early 20th century. Considered one of the country’s best preserved presidential sites, Coolidge’s home remains exactly as it was the night in 1923 when he was sworn into office as the nation’s 30th president; his father did the honors, right there in the parlor, upon receiving the news of President Warren G. Harding’s untimely death. Nearby, the simple but imposing whitewashed Plymouth Cheese Factory, established by the president’s father in 1890, is once again making its tangy, rich cheese.