Not to be confused with its notoriously funky neighbor to the south, Woodstock, Vermont exudes small-town charm and the upland lifestyle. Nestled in the heart of the Green Mountains along the banks of the Ottauqueeche River, Woodstock offers everything you could wish for from a gracious vacation, weekend, or full-time community. And at only a 2.5-hour drive from Boston? It’s surprisingly within reach.
Without exaggeration, Woodstock is a veritable outdoor playground. The flyfishing? World-class. Upland bird hunting? Just a short drive to the Northeast Kingdom. Alpine skiing? Not only are you surrounded by well-known options such as Pico Mountain and Killington, but Saskadena Six is located directly in Woodstock itself and is home to the oldest ski club in the east, providing both freestyle and racing programs for children ages 6-18. Is Nordic skiing more your style? Check out the Woodstock Nordic Center, with 45 km of groomed trails through the golf course and along historic carriage routes directly outside of town; they also accommodate snowshoers and fat bikers! And the list doesn’t stop there; there’s golf in the summer and fall, kayaking, sailing on nearby lakes, hiking galore, and a network of single-track, gravel, and winter mountain biking trails beautifully maintained by a devoted crew of volunteers at the Woodstock Area Mountain Biking Association.
Woodstock is not so rurally isolated that it lacks cosmopolitan comforts. Want to do a bit of shopping while in town? You’re in luck. The main village has store after store filled with exceptional home goods, clothing, books, art, crafts, jewelry, specialty grocery items, and more. My husband had to drag me out of RT Home, only to spend an hour himself in The Vermont Flannel Co. And F. H. Gillingham & Sons is just a fun experience in general (pun intended); stock up on everything from maple syrup to socks. Just outside of town is Simon Pearce’s studio in Quechee, which also boasts a fabulous riverfront restaurant in addition to his renowned collection of glassware. His son, Andrew Pearce, operates an impressive woodshop and gallery nearby that sells a beautiful array of handcrafted wood bowls, cutting boards, and platters. Perfect for all of that Vermont cheese!
There are a number of hotels and inns located in town or nearby. Perhaps the most well-known is The Woodstock Inn & Resort, located in the heart of the village. Founded originally as a tavern in 1793 and operated for a time by the Rockefeller family as part of the renowned RockResorts group, the inn is both historically charming and equipped with modern comforts, including restaurants, a spa, and an expansive athletic facility that includes golf and tennis. Smaller and located just south of town is the Kedron Valley Inn. This charming little spot even has a dining room open for dinner (Wed-Sun 5-9/10 pm) and is located next door to the South Woodstock Country Store, which is every bit as “Vermonty” as you want it to be. You can grab breakfast and/or lunch at the Country Store, which is convenient if you’re a guest at the inn, along with some pretty sinful toffee cookies, which is convenient for your personal trainer. If you’re looking for something decidedly more extravagant, explore Twin Farms in nearby Barnard, Vermont. A Relais & Chateaux property, this boutique luxury resort offers accommodations that range from rooms at the main house, lodge, and farmhouse to individual cottages and “tree houses”. Every room is equipped with a range of impressive luxuries from fireplaces and featherbeds to sumptuous linens and Stave jigsaw puzzles. The selection of private outdoor experiences is equally remarkable, including ski runs for your personal use, archery, ice fishing, and more. The restaurant and wellness programs look equally spectacular and have propelled Twin Farms to the top of our bucket list for our next trip through town. Barnard is only a 15-20 minute drive from Woodstock and sounds well worth the experience; do note that the resort is designed as an inclusive stay, therefore, facilities and amenities are available only to guests.
The restaurant scene in Woodstock is also more robust and exciting than in many rural towns. When we were last there, it was a Monday and although many eateries were closed, the trusty Woodstock Inn was open, had a log fire burning, and we gratefully whiled away our lunch over cold wine and hot clam chowder, which rivaled the very best New England has to offer. We’d hoped to try Santé, which is only open for dinner (Mon-Sat. from 5-9 pm), and we had to push south before dark, so next time! If you’re willing to venture outside of town, Worthy Kitchen is the spot for burgers and craft beer. And Cloudland Farm (open Fri and Sat. 5-10 pm) appears to offer a unique farm-to-table experience.
Woodstock has invested wisely in its community, its economic health, its independence—and it shows. You won’t miss the presence of big box retailers, and their absence is contributive to the health of the village’s stores, restaurants, and more. It’s also very much a year-round community, which is refreshing in a region where that’s not always the case. There are certainly times of the year that are a bit crowded, but it’s primarily only on weekends, and frankly, it comes with the territory in paradise. Whether you’re in town for a quick weekend, a longer vacation, or looking to purchase a property, Woodstock’s proximity to the Dartmouth-Hitchcock Medical Center in Concord, NH is also a comfort; it is not only a highly regarded medical research hospital, but it also has one of the few Level 1 Trauma Centers in New England. Woodstock is home to its own award-winning public school system (that includes its own high school) and is within reach of a handful of small independent and parochial grade school programs. It is also within easy driving distance to many of the region’s renowned private boarding schools, colleges, and universities.
If you’re thinking more long-term and/or looking for a place to call home? On weekends or more? Woodstock is, without question, worthy of investigation. And while you’re there, if you’d like to look into some listings? The Williamson Group Sotheby’s has an office right in town at 24 Elm Street, and an absolutely drool-worthy list of properties. They’ve been in the business for years, they know the region, and understand the market. Maybe at the very least, catch and open house while you’re in town and dream a bit of moonlit nights in Vermont!