Beginner Off-Road Trails
Near Cheshire, Massachusetts

This is a quiet and usually easy alternative route to ascend Mount Greylock, Massachusetts highest peak. While only open June through October, this gravely jaunt through the woods is more peaceful than the paved and more popular Rockwell Road. Eventually it does meet up with the paved main road, and...
Learn more about Greylock 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 into several other trails, some permitting ATVs and dirt bikes, and others for non-motorize...
Learn more about Bannis 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 Mountain. Views are mostly wooded, with some teases of mountains poking through the leaf canopy.
Learn more about Adams 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 spring or fall. Be sure to pay attention to the signs stating where the permitted motorized vehicle use en...
Learn more about Rounds Mountain DEC Access 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 small boat launch. This trail is a main access corridor leading to multiple off-shoot hiking trails in the Savoy Stat...
Learn more about Savoy Road/New State Road

This trail starts and ends on easier terrain, but the middle section is a nice little challenge. Dense hardwood forests, numerous babbling brooks, ancient stone bridges, a grassy field, and even a couple of mud holes are just some of the varied sights Stetson Road brings you through as you drive int...
Learn more about Stetson Road

Hallockville Road is a well-maintained dirt road through the Kenneth Dubuque State Forest. History abounds as you drive through this dense, but young mixed-wood forest. Incredibly good condition stone fences dart in and out of trees and large glacial erratics (boulders). The area was acquired by the...
Learn more about Hallockville Road

From the east, this road begins in Cummington, MA and heads west down a slight but rocky incline, into the Berkshire County town of Windsor where it is named Stearns Road. Mass DOT lists the road as in "intolerable" condition, and for most vehicles, this is spot on. Hardwood forests surround this se...
Learn more about Powell/Stearns Road

Ashley Lake Road is an old, unmaintained road through October Mountain State Forest. It rolls through hardwood forests past multiple lakes/reservoirs, including Ashley Lake, Sandwash Reservoir (this has a unique "aerator" which is a large fountain in the middle of the woods), Clapp Pond, and Mud Pon...
Learn more about Ashley Lake 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 waterfalls along several adjacent brooks. It is an unmaintained town road that skirts in ...
Learn more about Whitney Place to New Lenox 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 trail network. The only challenge would be numerous mud holes if driven during the we...
Learn more about Cowdry Hollow to Comstock Hollow Road

Middle Road is a well-maintained state forest road traversing the Kenneth Dubuque State Forest from South to North. Like the nearby Hallockville Road, this easy drive brings you through a young forest with a deep farming history. Multiple foundations can be spotted as you drive through mixed wood fo...
Learn more about Middle Road

This trail starts as a regular dirt road in a neighborhood. Soon after, the challenge starts. At the end of the neighborhood, you enter an overgrown two-track road, with >6 inch rock ledges that require higher clearance or good lines. When you reach the end, there is a steep downgrade full of large ...
Learn more about White Oak Road

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. Near the intersection with County Road is a small murky pond and c...
Learn more about Risky Ranch Road (VT TR 302)

Welcome to October Mountain State Forest, the largest state forest in Massachusetts. Lenox Whitney Place Road connects Country Road to the center of the Forest and all other trails within the park. Several trail options branch off throughout the entire trail. Please note signage that indicates what...
Learn more about Lenox Whitney Place Road

Serving as a perfect connection point to other trails, this trail is an easy dirt road with limited obstacles. Overall, it's a well-graded forest road winding through mixed hardwoods. The trail is wide enough for comfortable passing, and grades are mild. There's potential for shallow standing water ...
Learn more about Klondike 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 and the Berlin Pass. This road is inside Cherryplain State Park with lots of other activities, in...
Learn more about Schaeffer Road

Low risk, high reward. This trail through Monroe State has it all: a wooded drive, fantastic views, and amazing waterfalls. The trail has two names because it is a town road that passes through two towns, with a different name in each town. The very northern end of the trail crosses Dunbar Brook whe...
Learn more about Monroe/ Raycroft Road

Lower Tower Road is a short ride that leads to one of the nicest views in all of western Massachusetts. This is a very well-maintained graded gravel road that winds through the forest. Starting from the west heading east, prior to the trail is a paved section until you reach an ORV parking site. Fro...
Learn more about Lower Tower Road

Serving as a connection trail to County Road or the Klondike Trail, this trail is a simple, wide dirt road. Winding through the Vermont forest, you will be surrounded by a mix of hardwoods. It's a comfortable trail, with room to pass. If there's rain or wet ground, prepare to be muddy.
Learn more about County Road Connection

Ashley Lake Road is an old, unmaintained road through October Mountain State Forest. It rolls through hardwood forests past multiple lakes/reservoirs, including Ashley Lake, Sandwash Reservoir (this has a unique "aerator" which is a large fountain in the middle of the woods), Clapp Pond, and Mud Pon...
Learn more about Ashley Lake Road

Serving as a perfect connection point to other trails, this trail is an easy dirt road with limited obstacles. Overall, it's a well-graded forest road winding through mixed hardwoods. The trail is wide enough for comfortable passing, and grades are mild. There's potential for shallow standing water ...
Learn more about Klondike Road

Serving as a connection trail to County Road or the Klondike Trail, this trail is a simple, wide dirt road. Winding through the Vermont forest, you will be surrounded by a mix of hardwoods. It's a comfortable trail, with room to pass. If there's rain or wet ground, prepare to be muddy.
Learn more about County Road Connection

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 the dispersed campsites which include space for 1-2 cars and a fire ring but no bathrooms. There are n...
Learn more about US FSR 74

Ashley Lake Road is an old, unmaintained road through October Mountain State Forest. It rolls through hardwood forests past multiple lakes/reservoirs, including Ashley Lake, Sandwash Reservoir (this has a unique "aerator" which is a large fountain in the middle of the woods), Clapp Pond, and Mud Pon...
Learn more about Ashley Lake Road

Serving as a perfect connection point to other trails, this trail is an easy dirt road with limited obstacles. Overall, it's a well-graded forest road winding through mixed hardwoods. The trail is wide enough for comfortable passing, and grades are mild. There's potential for shallow standing water ...
Learn more about Klondike Road

Serving as a connection trail to County Road or the Klondike Trail, this trail is a simple, wide dirt road. Winding through the Vermont forest, you will be surrounded by a mix of hardwoods. It's a comfortable trail, with room to pass. If there's rain or wet ground, prepare to be muddy.
Learn more about County Road Connection

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 the dispersed campsites which include space for 1-2 cars and a fire ring but no bathrooms. There are n...
Learn more about US FSR 74