Beginner Off-Road Trails Near Winsted, Connecticut

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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…
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Total Miles
3.5
Tech Rating
3 Easy
Best Time
Sp / Su / Fa

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…
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Total Miles
0.9
Tech Rating
3 Easy
Best Time
Fa

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…
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Total Miles
2.6
Tech Rating
2 Easy
Best Time
Sp / Su / Fa / Wi

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…
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Total Miles
1.5
Tech Rating
1 Easy
Best Time
Sp / Su / Fa

Hartwood Club Road to Whitehead/Prosper Davis Road

Entering off the Route 48 side, the trail begins as a graded gravel road through a private forest preserve. This section of trail is very scenic and has a couple of interesting sights alongside it.…
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Total Miles
4.8
Tech Rating
2 Easy
Best Time
Sp / Wi / Fa / Su

Carpenter Road

Entering off Route 42, the trail will be marked with a town road and maintenance sign at the entrance. During Winter the entrance may be blocked by a snowbank. The trail is single-vehicle wide with…
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Total Miles
1.3
Tech Rating
2 Easy
Best Time
Sp / Su / Fa / Wi

Tannery Road

Entering off Route 42, the trail is marked with town road maintenance signs. During Winter months a snowbank may block entrance. The trail is one vehicle wide for its entire length. Downed trees will be…
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Total Miles
1.6
Tech Rating
2 Easy
Best Time
Su / Sp / Fa / Wi

Tannery Rd

Tannery road is a nice connecting off-road trail between Rt 125 and Rt 30. From north to south it starts off with a rocky uphill that transitions to some nice wooded trail. There is a…
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Total Miles
6.6
Tech Rating
3 Easy
Best Time
Su

King Road

Entering off Route 42, the trail will be marked with town road signs at the start. During Winter the entrance may be blocked by a snowbank. The trail is single-vehicle-wide with limited spots to pull…
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Total Miles
1.4
Tech Rating
2 Easy
Best Time
Su / Sp / Fa / Wi