Beginner Off-Road Trails Near Chappaqua, New York

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Two Towers Loop

Entering from reed road you will be taken to the trailhead, you will see wild animals from the adjacent safari park. Once you turn onto the trails you will be on soft Pine Barrens sugar…
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Total Miles
5.1
Tech Rating
3 Easy
Best Time
Sp / Su / Fa / Wi

Greentown Sale Road

Easy, seasonal forest road on the Delaware State Forest. It starts off in a small dirt lot off Old Greentown Road. The trail opens just before the state archery season in the fall and closes…
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Total Miles
0.7
Tech Rating
2 Easy
Best Time
Fa

River Road

This narrow woodland path turns into a narrow rocky shelf road along the Upper Delaware River. The trail is a non-maintenance Township and does pass through private property, STAY ON THE TRAIL! You will encounter…
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Total Miles
3.7
Tech Rating
3 Easy
Best Time
Wi / Fa / Su / Sp

Lake Atsion to Lake Oswego

A good introduction to Wharton State Forest and the Pine Barrens. Typically this is an easy route. Wet weather creates large "puddles" in depressions in the trail that require some attention. It makes for a…
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Total Miles
19.6
Tech Rating
2 Easy
Best Time
Sp / Su / Fa / Wi

Egypt Road Western Section to Tanner Falls

Non-maintained Western section of Egypt Road SR 4017. The trail is mainly gravel with the occasional rock or washout. downed trees and branches can be expected. The trail is one vehicle wide, and backing up…
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Total Miles
1.7
Tech Rating
2 Easy
Best Time
Fa / Su / Sp / Wi

T-743/T-727

The trail starts off in Poyntelle as Township-727 and in Winterdale as T-743. This section of the O and W Trail is a recognized Township route and is open to street-licensed 4x4s. The trail follows…
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Total Miles
12.8
Tech Rating
3 Easy
Best Time
Fa / Su / Sp

Big Valley Road

Big Valley Road is a long, winding, and rocky Forest Road through State Game Lands. Trail will not be plowed in winter. Downed trees can be encountered and the trail has a few muddy sections.…
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Total Miles
2.1
Tech Rating
2 Easy
Best Time
Sp / Su / Fa / Wi