For those interested in the Chester Station as a venue for parties, symposiums or day trips, we offer complete and up-to-date facilities. The 60x25 foot waiting room can become your themed banquet room. We are fully ADA compliant and offer central air. Up to 80 may be comfortably seated. You may supply your own food for a modest building rental fee, or tap the Foundation for complete preparation of your meal.
The Keystone Arch Bridges Trail is the place to go for trout fishing and during high water, offers Class III - IV rapids. There is easily more than one day’s worth of enjoyment here. Don’t have quite that much time? The Foundation can direct you to some vest-pocket hikes to an abandoned granite cutting works and a section of the Chester & Becket Railroad, which includes granite bridge abutments, and an intact wooden trestle. We can direct the visitor to the Historic Quarry and Trails operated by Becket Land Trust, a scant 5 miles up the road. This is another open air experience of historic and environmental significance, among the remnants of an abandoned mountaintop granite quarry.
Throughout the season, The Foundation presents a number of family-oriented events. The largest of these is Chester On Track, held traditionally on the weekend before Memorial Day, it encompasses all that’s special about Chester. With a hefty nod to the railroad, including a new locomotive open to the public, and a station full of railroadiana and toy trains, it’s been called a train show by some, but it’s really so much more.
The overlay is of a small town festival, with a parade, craft fair, petting zoo, antique and classic autos, set in an Historically Listed, unspoiled, 19th century village of shops and restaurants. It’s all here, railroad station, grocer, dry goods store, art gallery, restaurants, gift shop, old jail, and more. Savor a leisurely outing along Jacob’s Ladder Scenic Byway (U.S. Rte. 20) to Chester. Exit the Mass Pike exit in Westfield (take 20 west) or Lee (take 20 east). Plan to spend the day. Chester On Track has gotten high marks as a family-oriented day among the Berkshire foothills.
If it sounds like there might be a weekend worth of healthy activity for the family in Chester and environs, you’re right. Where to stay in the area? For an experience you’re sure to remember for a lifetime, consider spending the night in an antique wooden caboose parked next to the busy Boston Line. This is definitely to be considered a camping experience. You will need to supply your own sleeping bags, air mattresses, lanterns, etc. The caboose is operated by the Chester Foundation. Rates are $60.00 for the night, or $100.00 for the weekend.