Living in the Chester, Vermont Area

The Chester area of southern Vermont is comprised of Andover, Chester, Grafton, and Windham. 

Beautiful, Charming and Convenient to Green Mountain Attractions

Nestled in the southern Green Mountains of Vermont, the charming towns of Windham, Andover, Grafton, and Chester offer small-town living complete with quintessential Vermont village centers, working farms, historical sites and proximity to all the Green Mountains have to offer.

Those who live here value the friendly neighborhoods, village shopping, beautiful views, historic sites, and access to boundless recreational opportunities. The area is also just 30 minutes to Interstate 91, which connects you to all New England and beyond.

Love to Ski and Snowboard? Pick Your Resort!

Want a fantastic ski hub? Well, you can’t beat the Chester area for variety and convenience. You can drive to Okemo Mountain Resort, Magic Mountain Ski Area, Stratton Mountain Resort, or Bromley Mountain within 15 to 30 minutes. Can you think of anywhere else that gives you that kind of choice? Of course not, and that’s why skiers and riders flock to this area. Plus, if you love to cross country ski, you can blaze a trail minutes from your front door or choose from many cross-country ski parks, including Grafton Trails and Outdoor Center, Viking Nordic Center and Wild Wings Ski Center. Here, you will find groomed trails and hot chocolate waiting for you in the warming hut. 

Chester and Grafton Villages. A Must See.

Chester and Grafton have what are considered two of the best small-town shopping experiences in all of Vermont. 

Chester’s central park, called The Pinnacle, is surrounded by historic and charming inns, restaurants, and stores. In this tranquil and delightful community, you’ll also discover quaint B&Bs, unique shops, antique stores, and art galleries. Chester is also famous as one of the best-preserved examples of village architecture, including the distinctive collection of stone homes and buildings listed on the National Register of Historic Places.

Grafton is a timeless, quintessential New England village that has been preserved, stewarded, and financially supported by the Windham Foundation. As a result, this small town is thriving and features historic inns, taverns, galleries, churches, museums, the famous Plummer’s Sugar House, and the award-winning Grafton Village Cheese Company. Since 1892 the company has produced delicious, handmade, naturally flavored cheeses that sources from local farms and distributes its products internationally.

Hiking, Golf, and Summer Outdoor Recreation

In Chester, you can explore 550-acres of Town Forest trails, including the Lost Mine and Buttermilk Hill trails. Or explore the Green Mountain Trail with stunning views of the South Branch Williams River. Throughout the Green Mountain range, and especially in this region, there is plenty of beautiful nature to see and experience on a hike in this area. You’ll never get tired of the views as the colors and scenery changes with each season!

While there is so much to do in Chester, Grafton, Windham, and Andover, there are numerous activities all year round in the neighboring forests, lakes, rivers, and mountains. From snowshoeing in winter, to maple sugaring in spring, to world-class golf in summer, and finally, to the most beautiful foliage in the world in autumn, everything you would ever want to do in Vermont is at your fingertips.

Excellent Public and Private Schools

Windham, Grafton, Chester, and Andover all have a variety of outstanding school options for children. 

Area Elementary Schools 

Chester-Andover Elementary School: A public school located in Chester, VT, which has 252 students in grades PK-6.

Grafton Elementary School: A public school located in Grafton, VT, with 94 students in grades PK-6.

Area Middle and High Schools 

Green Mountain Union High School: A highly rated public school located in Chester, VT, with 319 students in grades 7-12 and a student-teacher ratio of 12 to 1.

Leland & Gray Union Middle/High School: A public school located in Townshend, VT, with 307 students in grades 7-12 and a student-teacher ratio of 9 to 1.

Getting Here and There

Chester is at the intersection of important southern Vermont routes. It is served by Vermont Route 103, Route 11 and Route 35. Interstate 91 is only 30 minutes from the center of town, and from there, you can reach anywhere in New England, New York, and beyond.

The area has easy access to the commercial hubs of Springfield and Manchester Vermont. Springfield is about 20 minutes away and has all the amenities you will need. Manchester is about a 30-minute drive and has outlet shopping, excellent dining, and plenty to do. 

The region is served by Amtrak trains, with a station in nearby Bellows Falls, VT (approximately 13 miles away). The closest regional airport is Rutland Southern Vermont Regional Airport (35 minutes away), with daily flights to Boston. Those who live in the area can drive to Bradley International Airport, or Manchester-Boston Regional Airport is about an hour and 45 minutes, where flight departures can take you anywhere in the world.

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Chester • Andover • Grafton • Windham