A trolley line from Waterbury to Woodbury was completed in 1908 and an amusement park was built on the Lake Quassapaug (formerly known as Quassapaug Pond) as a way to get workers and their families to ride streetcars and railways on weekends. Steady patronage due to the trolley connection helped transform the Quassy Amusement Park into a full-fledged summer resort.
Initially known as the Woodbury and Waterbury Street Railway it soon became part of the Waterbury and Pomperaug Valley Street Railway and was subsequently absorbed by the massive Connecticut Company - the primary electric street railway company in Connecticut. The line was abandoned in the 1930s when visitors began driving their cars to the resort.
A couple of sections of the trolley right of way (ROW) still remain and are "bike friendly." The Middlebury Greenway is a developed "official trail" but the section passing by the Woodbury Reservoir and following the South Brook is undeveloped.
Woodbury Trolley (Backwoods by the Reservoir)
I started at Old Sherman Hill Road and road south towards the Reservoir. It was all downhill and strangely much steeper on the section going north into Woodbury.
It's all downhill going west...
There's a small spot to park on Old Sherman Hill Road
-The Ride-
Old Sherman Hill Road
(pay no attention to the orange signs :-) )
The view up Trolley Bed Road at the start
I rode up to Route 64 first before I hit the woods...
It's a picturesque ride
Definitely glad I was on the mountain bike and not the road bike!
The classic embankment shot
At the end
Some spots were pretty overgrown!
I am found of embankment photos :-)
A bridge
All uphill going back but doable!
Panorama of the Woodbury Reservoir
Another Bridge
It took 20 minutes one way (going down) - probably 12-15 minutes if you wanted to bomb it. Going back - add at least another 5 minutes because its all uphill.
Middlebury Greenway
I next drove over the Middlebury to ride the Greenway. This follows the path of the old trolley ROW and has been fully paved, etc. It would have been better obviously on the road bike but the heavier bike and lots of hills made it more interesting for me.
-The Ride-
I started out from the FireHouse
There are a few historical signs along the way
The first climb goes through a beautiful rock cut
Oops - The official place to start!
This place is now a pizza joint!
Great info!
End of the line
(Mighty boring!)
Short One-Handed Video of the Trail
Sure it was somewhat boring compared to riding single track or a rutted abandoned ROWs in the woods but it was nice to see the Town feature the trolley line and the hilly up and downs made it fun.
Lunch
I grabbed lunch--which included a double IPA!--at this spot: Maggie Mcfly’s. It was wonderful and headed a bit south to Ride the Larking Bridle Trail.
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