Chester on Track Returns With Railroad-Themed Family Fun

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Chester on Track Returns With Railroad-Themed Family Fun

May 18 @ 9:00 am - 4:00 pm

The 33nd annual Chester on Track, presented by the Chester Railway Station, will take place 9 a.m. to 4 p.m. Saturday, May 20, featuring a wide range of activities all day for all ages at multiple locations in the Hilltown village often called “the gem of the valley.”

David Pierce, president of the Chester Foundation, said that 2,000 visitors are expected to attend, many from out of town and out of state.

“It helps the local economy,” Pierce said. “All the businesses usually have their best day of the year at Chester on Track, because there are so many people in town.”

Before the festivities begin, the Chester Foundation’s own Blue Caboose will open at the Historic Chester Railway Station at 8 a.m. for breakfast, and will offer a hearty railroad worker’s menu throughout the day where visitors can eat ‘hobo style’ in an antique wooden boxcar.

Events will be spread out on Main Street, at the library and Historical Society on Middlefield Road, at the Historic Chester Railway Station and grounds, and at the Chester Ballfield, where a lot of activities for the littlest kids will take place.  The ballfield is on Emery Street, not far from the station. Visitors can also hike a trail to the first American cluster of keystone arch railroad bridges, National Historic Landmarks, on the wild and scenic Westfield River.

The Hamilton Memorial Library will host a book and bake sale on the lawn and will have the Library’s mineral collections on display.  The Chester Historical Commission will be on hand at the Old Jail and Chester History Museum for tours from 9:30 a.m. to 3:30 p.m.

A parade at 10 a.m., will wind its way through Main St., with local historian Ed Carrington as the parade marshal.

A crafts fair, face painting and a “one-lung” steam and gas engine demonstrations will be along Main Street and on the lawn of the Chester Inn, along with the Jacob’s Ladder Business Association’s Business Expo. Also on the Chester Inn front porch will be live music throughout the day by the group Just Us.

Classic cars from Model Ts to the newest Corvettes will line up on Maple Street, where kids can also be entertained by Maggie the Railroad Clown, formerly of Ringling Bros. Circus.

Set up on the north lawn of the Chester Railway Station, a National Historic Landmark, will be Revolutionary War reenactors, a hand-hewn woodworking demo, a ham radio and Morse code demonstration and historic Civilian Conservation Corps camp exhibit.

A train show will be in the station, and commemorative envelopes and historical stamps with a special postal cancellation will be available all day for collectors.

Chester Station’s outdoor stage on the south lawn will host music by the Jenny Basset Duo, Janet Ryan Band, The 413s and Mark Franklin. The Pioneer Valley Live Steamers will display their large-scale operating steam and diesel locomotives and a selection of rolling stock on the station’s south lawn, along with a High Striker game from the Middlefield Fair, and one long John Deere engine that makes ice cream. A number of 1920s-era freight cars, including the 104-year-old wooden caboose and “Children’s Boxcar,” will be open to the public.

Just 600 feet down the road at the ballfield, where parking is also available, will be the Hampden County Sheriff’s Department K-9 demonstration, a steam train derby, kiddie train rides, bounce house, petting zoo, garden tractor pulls, and the Bottom’s Bistro taco stand. The Hilltown Family Center is also providing a self-guided story walk of “The Little Engine That Could” at the ballfield.

The Chester Fire Department will run its annual rubber duck race on the Westfield River in the afternoon.

More information on the history of the Chester Railway Station and the keystone arches  may be found at For more information about Chester on Track, visit online or call 413-354-7878

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May 18
9:00 am - 4:00 pm


The Chester Foundation
(413) 354-7878
View Organizer Website


Chester Railway Station
10 Prospect St.
Chester, MA 01011 United States
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View Venue Website