Woodstock blends small-town appeal with scenic landscapes
The town of Woodstock helps New England earn its reputation for quaint small towns. “Woodstock gets written up all the time as one of the prettiest small towns in America. It’s a Norman Rockwell-style town filled with charm,” says Gretchjen Smith, a Realtor at Williamson Group Southeby’s International Realty with nearly 20 years of experience. “It has beautiful, old historic homes. It’s anchored by a huge green that has the beautiful Woodstock Inn. It has skiing and year-round activities.” Brick storefronts line the downtown streets, housing small local businesses and restaurants, while the surrounding landscape features rolling hills with miles of trails for hiking and skiing. The mix of recreation and small-town charm has made Woodstock a popular destination for tourists and homebuyers.
Classic New England housing styles add historic charm to downtown
Federal-style and Colonial Revival homes from the 1800s and early 1900s are common in town, often with brick exteriors or white siding. Downtown homes sit close together on streets lined with sidewalks. White picket fences often wrap around the yards, adding to the small-town scenery. The green lawns are well-maintained, and leafy trees surround most homes. Cape Cods, ranch-style houses and farmhouses are also typical, especially in the more rural parts of town. These properties are often 5 acres or more and sit on winding country roads among fields and forests. The median sales price in Woodstock is around $880,000, higher than nearby towns like Hartford or Lebanon , New Hampshire.
Local businesses sell home goods, groceries and specialty foods
Woodstock’s downtown is full of small businesses, including home goods shops, a general store, sporting goods retailers and several restaurants. “Gillingham’s is a must. That’s the old general store. If you come to town, you have to go there,” says Smith. “There are lots of cute little home decorating shops. My new favorite is Woodstock Home.” F.H. Gillingham & Sons has been open since 1886 and sells locally made foods, clothing and other specialty products. Restaurants in the area range from casual cafes for a morning cup of coffee to fine dining. The Prince and the Pauper is an upscale spot serving a prix fixe menu. Smith recommends Sante for farm-to-table small plates. Groceries are available at the Woodstock Village Market. Big-box stores are just 15 miles away in Lebanon, New Hampshire.
Year-round recreation at local parks and natural areas
Woodstock offers four seasons of outdoor activity. The Marsh-Billings-Rockefeller National Historical Park is an estate that multiple prominent families inhabited before being donated to the National Park Service. Today, the estate’s 20 miles of trails are open for hiking in spring, summer and fall. In the winter, the Woodstock Inn & Resort Nordic Center maintains 12 miles of cross-country skiing and snowshoeing trails. Visitors must purchase a day pass from the Nordic Center before visiting. The estate’s mansion is also open for tours from May through October. Across the street, the Billings Farm & Museum recreates life on the farm in the 1800s. Mt. Peg is a natural area near downtown offering a 2.5-mile hike to the summit, plus more cross-country skiing. Vail Field offers a traditional city park with sports fields, a playground and a picnic shelter. Other outdoor activities include downhill skiing at Saskadena Six or fly fishing on the Ottauquechee River.
Highly rated schools close to home
Students might attend Woodstock Elementary School and Prosper Valley School, each rated A-minus by Niche. Woodstock Union High School and Middle School serves seventh through 12th grades and earns a B-plus. The school offers 16 Advanced Placement courses and a 74% pass rate. Students can also enroll in dual enrollment courses through institutions like the University of Vermont, Vermont Technical College and Norwich University. The Hartford Area Career and Technology Center offers training in industries like business administration and information technology.
Weekly and seasonal events honor Vermont culture
Woodstock celebrates its heritage with several weekly and annual events, many taking place on The Green in the center of town. Market on the Green takes place on Wednesday afternoons and features local vendors selling produce, crafts, food and more. The Apple and Crafts Far & Food Truck Festival features over 100 vendors selling crafts and specialty foods. The holiday season brings the annual Wassail Weekend, which includes a parade through the village, horse and carriage rides, a rare book sale and tree lighting.
Flood zones and low crime shape local safety profile
U.S. Route 4 is the main highway through Woodstock. It leads about 15 miles east to Lebanon and connects to Interstate 89 about 10 miles east. Route 4 also leads about 31 miles west to the city of Rutland . The closest hospital and airport are both in Lebanon.
Flood risk along the Ottauquechee River
Areas along the Ottauquechee River and Kedron Brook are at risk of flooding. Flood maps are available from the Vermont Department of Environmental Conservation. Woodstock’s CAP Index Crime Score is 1 out of 10, considerably lower than the national average of 4.
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Written By
Matthew Atkins
