Chester, Vermont: Small-Town Living in the Digital Age

© Jared C. Benedict.

© Jared C. Benedict.

Located in the scenic Green Mountains, Chester, Vermont is a thriving town with a strong sense of history and place. Easily accessible from I-91, we are a picturesque, engaged community providing a wide range of four-season activities making for a uniquely rich quality of life for our residents and visitors alike. 

Chester's Stone Village Historic District and its sweet main street and green claim spots on National Register of Historical Places. New England Travel Today recently named Chester one of the ten best antique towns in all of New England. 

Enjoying the outdoors comes second nature to us; we're active in our own backyards and we take advantage of our proximity to Bromley, Stratton, Magic Mountain, Mount Snow, Okemo Mountain Resort, and Killington. 

Lately, the buzz has revolved around our blazing fast, reasonably-priced internet speed. Lucky us, we're at the center of one of the U.S.'s fastest fiber optic cable networks in the United States making us one of the best connected communities in the nation. Whether you're visiting Chester, Vermont for the weekend or considering a move here, we're happy to show you around and give you a taste of what makes being here so special.

  • In the tiny town of Chester, Vermont — population 3,144 — you can leisurely stroll through vintage barns and shops selling country furniture, hooked rugs, woodenware, textiles, collectibles, jewelry and coins. The Stone House Antique Center features more than 90 dealers in nearly 20,000 square-feet of space.
    — Necee Regis, New England Today
  • Beyond the village border, you’ll pass historic Chester Depot before straying into deep countryside. Pavement morphs into dirt (the Green Mountain State is home to more dirt roads than paved), and suddenly it feels as though you’re stepping off the map into uncharted Vermont. Red barns sprout up, ubiquitous as milkweed in late summer, along with enough winding stone walls to defend a medieval village.
    — Annie Graves, Yankee
  • We discovered the pretty little town of Chester by accident on our way to Okemo Mountain Resort. It’s tucked into the southeast corner of Vermont, where three branches of the Williams River meet, surrounded by rolling farmlands and Green Mountain peaks. Chester, Vermont has two historic districts, which should put it on the map for history and architecture buffs. The Stone Village Historic District has 10 beautiful Greek Revival buildings, made of stone from local quarries. A few blocks away is the Chester Village Historic District, with a mix of significant Victorian and Federal-style buildings, now housing a cluster of shops and inns.
    — Diane Blair, Boston Globe

Experience Chester, VT


Learn what to do, where to go, and what to try with these
handy guides for visitors and residents alike.


Where to Shop
in Chester, Vermont


Where to Stay & Eat
In Chester, Vermont


Where to go
In Chester, Vermont

Photo credit: © Chester Telegraph

Chester's Stone Village, ©  Magicpiano /  CC BY-SA 3.0

Chester's Stone Village, © Magicpiano / CC BY-SA 3.0

Things to Do
IN Chester, VT

There's no shortage of things to see and passions to pursue in Chester, Vermont. Our local park, The Pinnacle, is a nexus of much of the town's outdoor activity; while our beautiful green at the center of the village serves as a focal point for several annual community traditions and festivals. 

The Chester Fall Festival, © Lew Waters

The Chester Fall Festival, © Lew Waters

In Chester, VT

Top banner photo credit:
Tyler Goodrich / CC BY-SA 3.0