Events & Activities > Things to Do in Chester

A year-around holiday hub, the town of Chester is the perfect base whether you are enthusiastic about history, antiques, outdoor pursuits or simply taking joy in the steady rhythms of small town life. Check our calendar to be sure not to miss the town's many annual events, including its ever-popular Fall Festival in September.


EXPERIENCE Chester

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Local Culture & History

Situated at the gateway to the Green Mountains, Chester served as a major hub of commerce activity in Southern Vermont at the end of the 19th century. Fortunately many of our historic buildings, including the Yosemite Firehouse and the Chester Depot train station remain. Beautiful Victorian homes capped with cupolas and iconic stone homes, preserved with care, line our streets. A small suspension bridge crosses the Williams Middle Branch at the end of School Street linking a lovely walk around our village. The steeples of our many churches rise high over the treetops.

While some things have changed, other mainstays of our local culture remain; including maple sugaring season, which remains a delicious way to welcome spring. Here in the fall? The Green Mountain Railroad offers rides from Chester from September 16th-October 15th 2017.

Plus: See Maps & Resources for a downloadable walking tour!


Outdoor PursuitS

Chester's town recreation park is located "at the Pinnacle" on the west side of town. In the summer, residents and locals flock to the Pinnacle to enjoy our large town pool, our skateboard park, tennis courts, a playground, disc golf course, and gazebo for picnicking. In the winter, we take to the ice, playing broom hockey, ice hockey, and simply enjoying some ice skating on the town rink located at the Pinnacle. The VAST trail system runs right through here, drawing snowmobilers eager to see our town's beauty and hop off for lunch at one of our many restaurants. 


Skiing & Snow Sports

Chester is conveniently located with several nearby downhill and cross-country resorts and centers.