Beginner Off-Road Trails Near Cheshire Village, Connecticut
Roaring Brook Road
This trail skirts the edge of a very marshy section of the Housatonic River. This trail is mostly flat, with some large dried-up mud holes and a few washed-out sections. 4WD is not necessary, though… Learn more about Roaring Brook Road
Total Miles
1.8
Tech Rating
1
Easy
Best Time
Sp / Su / Fa
Whitney Place to New Lenox Road
This is an easier trail with some deep mud holes and numerous small rocks along the trail. It brings you to the secluded and picturesque Farnham Reservoir (City of Pittsfield) which provides plenty of cascading… Learn more about Whitney Place to New Lenox Road
Total Miles
3.5
Tech Rating
3
Easy
Best Time
Sp / Su / Fa
Deane Hill/Rossiter Road
This is a simple trail composed of a seasonal and an unmaintained road. The track bounces from Massachusetts to New York and back again to Massachusetts. The terrain is rolling and varies from old farm… Learn more about Deane Hill/Rossiter Road
Total Miles
1.9
Tech Rating
1
Easy
Best Time
Sp / Su / Fa / Wi
Bannis Road
Bannis Road is an unmaintained road, open June 1st through December 30th. A rolling, wooded trail, it is easily completed with any high-clearance vehicle, with only a few deep gullies and ledges. It does feed… Learn more about Bannis Road
Total Miles
2.5
Tech Rating
2
Easy
Best Time
Su / Fa
Adams Road
Adams Road is a deeply rutted and muddy road that descends from near an active fire tower (with a gated access road, but hiking up to it is permitted) down the northeast side of Borden… Learn more about Adams Road
Total Miles
1.6
Tech Rating
2
Easy
Best Time
Su / Fa
Savoy Road/New State Road
This is a very gentle dirt road with a mildly more difficult center section that is not maintained. The real gem of this trail is the access it provides to Bog Pond, which includes a… Learn more about Savoy Road/New State Road
Total Miles
3.9
Tech Rating
1
Easy
Best Time
Su / Fa / Sp / Wi
Rounds Mountain DEC Access Road
This is a short but rewarding drive for a novice of roader, or just someone looking for an easy day out. It provides some nice views of the Berkshires and pleasant topography, especially in the… Learn more about Rounds Mountain DEC Access Road
Total Miles
0.9
Tech Rating
3
Easy
Best Time
Fa
Schaeffer Road
This route starts as an easy track curving through thickly wooded state land. It eventually rises to a ridge with decent views of the west and spectacular views to the east overlooking the Taconic Ridge… Learn more about Schaeffer Road
Total Miles
2.4
Tech Rating
1
Easy
Best Time
Sp / Fa / Su
Cowdry Hollow to Comstock Hollow Road
This is a well-maintained state access road with wooded valley views, numerous adjacent brooks, and multiple side hiking trails. It is part of the Berlin State Forest and provides access to the Taconic Crest hiking… Learn more about Cowdry Hollow to Comstock Hollow Road
Total Miles
2.6
Tech Rating
2
Easy
Best Time
Sp / Su / Fa / Wi
Risky Ranch Road (VT TR 302)
An alternate exit/entrance from County Road, this trail is a muddy, rocky, and rutted path through mostly hardwood forests. There are several instances where alternate paths avoid rockier terrain but travel through murky muddy pools.… Learn more about Risky Ranch Road (VT TR 302)
Total Miles
2.5
Tech Rating
2
Easy
Best Time
Sp / Su / Fa
US FSR 74
This is a well-maintained gravel road flanked by forests and dispersed campsites on either side. There is a gate at the entrance which is closed from December 15th to May 1st. Camping is allowed at… Learn more about US FSR 74