About Us






Book the Chester Station!






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.


Our Prices:

$100.00 for the station building alone.  Add $50.00 for the use of the 'Blue Caboose' kitchen facility.  This is a complete kitchen.  Station comes with sinks, 2 microwaves and a refrigerator. 


Wooden caboose overnight camping is $60.00 for one night, $100.00 for two. This includes access to the station bathrooms.

 Please note:  these prices have remained unchanged for 10 years.



Click Here for booking an event at the Station


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.


Chester, Massachusetts


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.


Outdoor Activities


We are also the place for outdoor activities of a unique nature.  As the official visitors center for the Keystone Arch Bridges Trail, we can set you on the path of one of the most impressive historic and environmental experiences you can have all in one hike.  You will see the most impressive series of railroad bridges imaginable, all the while discovering the wonders of the largest road-less wilderness in the Commonwealth.  Twisting through this setting is the West Branch of Massachusetts’ first Wild & Scenic River, the Westfield.  This was recently named the healthiest river in the state by the Nature Conservancy.


The Blue “Kitchen” Caboose





The Chester Foundation’s own ex-B&O C-26 class steel caboose shows off its new livery in Sept of ’05.  These cars were built by International Car Co. in 1971, among the last batches of new cabooses built in this country.


The museum uses the caboose as a kitchen for the facility.  Many delicious dinners have originated here, as well as tasty soups and grinders for more informal events.  The museum’s all-volunteer food service staff can put on a well-prepared and attractively presented meal for any occasion.


The original paint scheme was solid blue without the white band.  Capitol herald is in its approximate original position.  While the lightning bolts bracketing the FOOD SERVICE banner, surely denote quick service, knowledgeable fans will make the connection to the popular “Radio Equipped” caboose and locomotive slogans of the late ‘50’s and early 60’s.  CSX’s newest locomotives still carry the lightning bolt symbol, with no printed qualifier.




During Chester On Track, the Blue Caboose will be serving all day from the platform side window.  Patrons can cross the platform to enjoy their meal in one of two ex-B&M outside-braced XM-1 boxcars owned by the museum.  These wood-side cars were unique to B&M due to their distinctive end panels, used on no other cars ever built.  This track side eatery has proven very popular with station visitors.



Chester On Track

Something to remember:

Chester On Track is always held on the weekend before Memorial Day every year!

















The Keystone Arches





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. 


Antique Wooden Caboose 




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.


Click Here for Caboose Rental Info...



What is The History of Chester’s ‘Historic Caboose’?






The ‘other’ caboose on the Chester Foundations’ museum grounds, New York Central standard wood caboose, is a bit of an imposter.  It is dressed to look like a member of the well-known fleet, as shown here.  In point of fact, it is former Rutland Railroad no. 32.  These way-cars were built to plans supplied by parent road, NYC during the First World War.


The Foundation is fortunate to possess numerous papers related to the design and execution of the construction of this car.  This caboose was generously donated to the museum by Mr. John Carlson.




The main distinguishing features to tip off its true heritage are the lacy ladder tops, and the racy rain gutters over each window, missing on their NYC cousins.  Many of the cars, including no. 32, wore the later, more colorful, green and yellow scheme, shown here.


This caboose was under the stewardship of a Conductor Ellis “Pee Wee” Stone, described as kind of a wild man with both a temper and a sense of humor.  He is said to have been a very professional railroader and was a shop steward.  There have been quite a few Pee Wee stories printed in the

RRHS Newsliner magazine.





None of the wooden cabooses, so far as we are aware, carried both an NYC oval herald and a number in the Boston & Albany series (as does our hybrid).  Interestingly, some later, steel bay window cabooses, did have both painted on their sides.


Beside the ‘boxcar red’ scheme, NYC wood cabooses have worn jade green and the Pacemaker, red and grey scheme.  One wore the unique Safety layout. Those, and the two Rutland schemes shown, are not out of the question as candidates for future re-paintings.  Send us your thoughts.


Thanks to Will Davis,

Rutland Historical Society,

for the information on the life of our caboose on the high iron.



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P.O. Box 743, Chester, MA, 01011