Woodstock: 16 miles W of White River Junction; 140 miles NW of Boston; 98 miles SE of Burlington
For more than a century, the resort community of Woodstock has been considered one of New England's most exquisite villages, and its attractiveness has benefited from the largesse of some of the country's most affluent citizens. Even the surrounding countryside is, by and large, unsullied -- it's pretty difficult to drive to Woodstock via any route that isn't pastoral and scenic, and by the time you're here you're already feeling as if you're back in some other, slower-paced era. Few New England villages can top Woodstock for sheer grace and elegance; its tidy downtown is compact and neat, populated by galleries and boutiques. The lovely village green is surrounded by handsome homes, creating what amounts to a comprehensive review of architectural styles of the 19th and early 20th centuries, and you could literally throw a stone (but don't) from the town center and hit a fine covered bridge.
In addition to Woodstock, this region also takes in nearby White River Junction, Quechee, and Norwich, three towns of distinctly different lineages along the Connecticut River on the New Hampshire border. In fact, while here you'll want to cross over the river to Hanover, New Hampshire, a lovely town that's home to Dartmouth College.
Much of Woodstock is on the National Register of Historic Places already, and -- as if that weren't enough -- the Rockefeller family deeded 500 acres surrounding Mount Tom to the National Park Service to protect even more of it from developers. In fact, locals occasionally joke that downtown Woodstock itself could be renamed Rockefeller National Park, given the attention and cash the Rockefeller family has lavished on this town in the interest of preservation. (For starters, Rockefeller money built the faux-historic Woodstock Inn and paid to bury unsightly utility lines around town.)
The village, which sits on the banks of the gently flowing Ottaquechee River, was first settled in 1765 and it rose to some prominence in its day as a publishing center: No fewer than five newspapers were being published here in 1830. Soon, it began to attract wealthy families seeking cool solace from the big city. To this day, Woodstock feels as if it should have a prestigious prep school just off the green, and it comes as a real surprise that it doesn't. A Vermont senator, in the late 19th century, noted that "the good people of Woodstock have less incentive than others to yearn for heaven," and that still applies today.
Wealthy summer rusticators were instrumental in establishing and preserving the character of the village, and now the moneyed class has turned its attention to the many handsome farms outside town and on the dirt roads along the river and in the foothills. Few of these former dairy farms still produce milk anymore; those barns that haven't already been converted into architectural showcase homes more than likely house valuable collections of cars, art, or antiques.
The town is also notable as a historic center of winter outdoor recreation. The nation's very first ski tow (a rope tow powered by, yes, an old Buick motor) was built in 1933 at the Woodstock Ski Hill near today's Suicide Six ski area. There are no huge mountains hereabouts, and maybe that's why this is definitely no longer the center of Vermont's skiing universe (maybe Stowe is?) -- but that's actually a very good thing. Low-key Woodstock is growing more upscale, yet it remains one of my very favorite small towns in New England -- a great place summer, winter, or fall to hike, bike, skate, cross-country ski, snowshoe, or simply window-shop and leaf-peep.
Speaking of leaves, I need to caution you that Woodstock's excellent state of preservation and outstanding foliage haven't gone unnoticed. The secret is out, and this place draws hordes of travelers during peak foliage season (usually early to mid-Oct), when the town green is practically obscured by the tour buses continually circling it. Ideally, that's when you would want to come; just don't expect quiet and peaceful streets or uncluttered roads when you get there.
Note: This information was accurate when it was published, but can change without notice. Please be sure to confirm all rates and details directly with the companies in question before planning your trip.