Chester Train Rides​
535 Depot Street, Chester VT, 05143

About

Vermont Rail System’s story begins with the closing of another. By the fall of 1963, the end of the Rutland Railway was in sight, and it was sold to the State of Vermont. Jay Wulfson, an experienced railroader from East Brunswick, N.J., expressed interest in operating the line and restoring rail service to Western Vermont, following a nearly two year service interruption caused by labor strikes on the Rutland. On August 6, 1963, Wulfson signed a lease agreement with the state to begin operations. President Wulfson, along with Vice-President Harold T. Filskov, Charles Bishoff, and an ambitious team, set off to run the nation’s first privately owned railroad operating on publically-owned right of way... Read More


Chester to Ludlow 
Weekday Fall Foliage Excursions

Chester to Ludlow - 2 hour round trip - No layover

September 16 – October 15, 2017​​
Tuesdays & Thursdays
3 departure times each day

Come visit us in Southern Vermont for a historic and beautiful Fall Foliage train ride. This train goes North from Chester to Ludlow and back. We will roll past quintisential Vermont towns, over rivers, and through the trees of the Green Mountains to show you the back woods of Vermont's Culture and the beautiful Foliage we have to offer.

Our visitors love going over the Tressel in Ludlow where you can see the town of Ludlow, foliage and the slopes of Okemo Mountain Resort.   


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Chester to Okemo
Weekend Fall Foliage Excursions

Chester to Okemo Mountain Resort - 2 hour round trip - With Layover

September 16 – October 15, 2017​​
Saturdays & Sundays

Come visit us in Southern Vermont for a historic and beautiful Fall Foliage train ride. This train travels North from Chester Vermont to Okemo Mountain Resort and back. We will roll past quintisential Vermont towns, over rivers, and through the trees of the Green Mountains to show you the back woods of Vermont's Culture and the beautiful Foliage we have to offer. This train will take you up to one of Vermont's finest mountain resorts. Click below for more details and weekend specials.
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Green Mountain Dinner Train
Green Mountain Fall Foliage Dinner Train

Chester to Ludlow - 2.5 hour round trip - no layover

September 16 – October 15, 2017​​
Friday and Saturday Nights

Come join us for dinner on the rails in Southern Vermont. This train ride gives you the chance to see the Fall Foliage during sunset while enjoying a 4 course meal catered by one of Ludlow's finest restaurants. This train goes North from Chester to Ludlow and back for a 2.5 hour round trip.

This year we will be starting an hour earlier for our guests to really enjoy the foliage during their ride. 
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