Saturday, May 21, 2022 from 9:00am to 4:00pm

CHESTER, MA- Journey to Chester On Track, the 21st annual railroad-themed family festival in downtown Chester, MA on Saturday, May 21 from 9:00am to 4:00pm, held rain or shine. The event gathers some of the very best early industrial, railroad, military and artisan talent from three states. The event is FREE (donations accepted) and wheelchair accessible.

A 10am parade sets the pace for the day along Route 20 and through the downtown led by 2011 Parade Marshall Senator Michael Knapik. The Senator will also present a proclaimation recognizing the 170th anniversary of this pioneering railway.

Guests may visit with living history re-enactors from the, 10th Massachusetts Regiment Civil War, Continental Regiment Revolutionary War, Civilian Conservation Corps and Storrowtown Village Irish immigrant railroad workers. Stop by the train show at the depot & craft fair on the lawns of the Chester Inn. Marvel at the Pioneer Valley Live Steamers large scale steam locos the station grounds and the ‘one-lung’ steam & gas engine demos on Main St. There will be classic cars from Model ‘T’s to Corvettes and everything in between.

Other displays include a number of 1920’s-era freight cars, wooden caboose, wooden velocipede, 1930 Vulcan steam engine, and Children’s Boxcar. Visitors can rest their feet with a sightseeing rides by “Maggie Saw Horse,” or horse-drawn wagon. Take a helicopter ride above the village or check out the abandoned stone finishing works, in walking distance of the depot. Take a bus tour, departing hourly, to the Chester Granite Company for contemporary stone finishing demos.

Live entertainment all day features the Pioneer Valley Fiddlers, The River Dawgs, and The Electric Trains, sponsored by the Chester Cultural Council, a local agency supported by the Massachusetts Cultural Council. Linda Burns will also provide musical entertainment at the Chester Inn on Main Street. Bring your appetite; a wealth of good food is available for the day. The Blue Caboose café at the museum offers a variety of grinders, soups and desserts. Local restaurants offer fine culinary fare, and food vendors round out the choices along Main Street. A 50/50 raffle, with secondary prizes of train rides on the Vermont Flyer and Berkshire Scenic Railway is offered too.

Also a highlight, a short drive from downtown Chester, is the Keystone Arch Bridges (KAB) Trail (a moderate hike is involved), featuring seven historic 1839 stone arch railroad bridges, (America’s first) engineered by George Washington Whistler (father of artist, James McNeil Whistler). The bridges span the Westfield River, rising in some places 70 feet above the water, carrying the former Western Railroad, (now CSX) on a 100 foot-per-mile grade over the Berkshire Hills. This heralded engineering accomplishment proved the ability for rail travel over mountains, spawning population expansion from New England to the west.

The event is sponsored by the Chester Foundation, a philanthropic group dedicated to community improvement and preservation. Admission to event is free, reserved parking is $1. Chester is located on Route 20 along the Jacobs Ladder Scenic Byway, between Lee and Westfield. For more event information call (413) 354-7878 or visit