There used to be a race here and many of the trail markings are still there but a lot of washout has happened and you'll need to look for the newer connecting single track for the area
From Rt 8/44 intersection follow 44 into Winsted. Right after Town Hall onto Elm St. Straight up hill to STOP sign. Left on Hinsdale Ave. Right at STOP sign to The Gilbert School. Drive up hill to right of school and look for old dirt log road at top of hill.
http://www.singletracks.com/item.php?c=1&i=7175