Living in the Chester, Vermont Area

Chester, VT

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

Beautiful, Charming and Convenient to Green Mountain Attractions

The Green Mountains provide a beautiful backdrop for the towns of Windham, Andover, Grafton and Chester. With their charming village centers, working farms and historic sites, these towns offer a peaceful and relaxed small-town lifestyle. Residents enjoy easy access to all the great outdoor recreational activities that Vermont has to offer, from skiing in the winter to hiking and camping in the summer. Shopping or dining at one of the many local businesses adds to the unique experience of living here. Just a short drive away is Interstate 91 which connects you to cities and states beyond, further extending your options for getting out of town or exploring what New England has to offer. Living here is an opportunity like no other!

Love to Ski and Snowboard? Pick Your Resort!

Skiers and snowboarders rejoice in the Chester area, as it is home to some of the best ski and snowboarding resorts in all of Vermont. In just 15-30 minutes, you can be in the chairlift at Okemo Mountain Resort, Magic Mountain Ski Area, Stratton Mountain Resort or Bromley Mountain - a variety that cannot be matched anywhere else! For cross country skiers, Grafton Trails and Outdoor Center, Viking Nordic Center and Wild Wings Ski Center are here to provide groomed trails for your skiing pleasure. And after a day on the slopes, reward yourself with a mug of hot chocolate waiting for you in the warming hut.

Chester and Grafton Villages. A Must See.

Chester and Grafton offer some of the most unique and charming shopping experiences in Vermont. At Chester's The Pinnacle, visitors can find inns, restaurants, stores, B&Bs, shops, antiques and art galleries - all lovingly preserved throughout the years. As part of a National Historic Register location, you won't find buildings quite like these anywhere else!

Grafton village offers a timeless New England experience that has been preserved for generations by the Windham Foundation. Here you'll be able to explore historic inns, taverns, galleries and churches. Don't miss out on trying a sample at Plummer's Sugar House or grabbing something to snack on from the award-winning Grafton Village Cheese Company - they've been hand crafting delicious cheeses since 1892!

Hiking, Golf, and Summer Outdoor Recreation

The Chester area is a nature lover's paradise, with 550 acres of Town Forest trails and the Green Mountain Trail - both offering stunning views of the South Branch Williams River. With changing colors and scenery every season, there's never a dull moment! But it doesn't end there; in addition to all this beauty, there is plenty of fun to be had in the surrounding forests, lakes, rivers and mountains. Winter brings snowshoeing, spring brings maple sugaring, summer offers world-class golf courses, and autumn presents the most incredible foliage you'll ever witness. No matter what time of year you visit this region of Vermont - you won't be disappointed!

Excellent Public and Private Schools

Windham, Grafton, Chester and Andover are home to a variety of exceptional schools. From public and private elementary schools to acclaimed Vermont country day schools, these small towns offer a range of educational options for all ages. Public schools in the area provide quality education while also promoting community values such as respect and service to others. Private schools provide students with additional opportunities to explore their interests through individualized learning approaches and unique extracurricular activities. Country day schools offer a highly personalized approach where each student is taught at their own pace and empowered to take ownership over their own education. No matter your educational needs or preferences,Windham, Grafton, Chester and Andover offer something for everyone!

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