Thanks to everyone who attended our 2023 Chester On Track Festival. More people always make it more fun! 

We also want to thank all the vendors and volunteers who handled everything from set up to clean up to making sure everyone was happy and had what they needed.

Mark your calendar for Saturday, May 18th, 2024 for
The 33nd edition of Chester On Track

Saturday - May 20th, 2023 | 9AM - 4PM | Rain or Shine

Our Massive Parade Begins at 10AM

Events All Day At Multiple Locations

Activities And Times Subject to Last Minute Changes

Chester Railway Station

Blue Caboose

  • Breakfast Served 7am -10:30am
  • Lunch served 11:00am – 3:00pm

Inside The Station

  • Model Train Displays
  • Postal Cancellations
  • Station Gift Shop
  • Specialty Vendors

Main Stage - Live Stream
  • The Jenny Basset duo
  • Janet Ryan Band
  • The 413’s and
  • Mark Franklin.
  • In case of rain, Town Hall Stage

Station Grounds

  • Revolutionary War Re-Enactors
  • High Striker Game
  • Hand hewn woodworking demo
  • Westfield River Wild & Scenic Fish Prints
  • Ham Radio and Morse Code demo
  • CCC Camp Exhibit
  • Delta Square Axe, Rustic Tool Demo
  • Pioneer Valley Live Steamers

Duck Race - 2PM

  • Start: Hamilton Emery Company on Middlefield St.
  • Finish: Under the Main St. Bridge.


  • ‘Autumn’s Bistro’, Taco’s, Cotton candy on Chester Ballfield
  • Boy Scout Food Booth
  • Blue Note/Classic Pizza on Main St
  • Chester Common Table on Main St.
  • Carms Restaurant and Coffee Shop on Rt 20
  • The Blue Caboose at the Station.

Main Street

  • Craft Fair & Plant Sale
  • Face Painting
  • Steam “one-lungers” & Gas Engines
  • Chester Fire Dept. Duck Race 2PM
    Tickets $5 each or 5 tickets for $20
  • Drowsy Dragon Gourmet Treats
  • Kettle Corn
  • Free Wagon Rides
  • Sheriff and Ambulance
  • Boy Scout Food Booth
  • Baptist Church Info
  • Music by Just Us (on the porch of Chester Inn)

Maple Street

  • Classic Cars
  • Antique Tractors

Riverfront Street

  • JLBA Home Show
  • Antique Fire Truck
  • Chester Fire Department

Chester Ball Field - The Fun Spot

Huntington Rd/Route 20

Hamilton Library

  • Book and Bake Sale on the front lawn
  • Mineral Collection Open for Tours

Old Jail House and Chester Historical Museum

  • Open for tours
Site Map

Mass Appeal’s 2023 Chester On Track Segment

A Fun Time Every Year

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