Beginner Off-Road Trails Near Great Barrington, Massachusetts

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

This is a dirt road whose center section is seasonally unmaintained. It skirts through the woods among private property and Beebe State Forest. You'll pass through ravines, hardwood groves, and over a small ridge on…
Learn more about Old Macedonia 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

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

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…
Learn more about Ashley Lake 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

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…
Learn more about Greylock 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

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…
Learn more about Powell/Stearns 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

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

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

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

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…
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…
Learn more about Hallockville 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…
Learn more about Middle 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.…
Learn more about Risky Ranch Road (VT TR 302)

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…
Learn more about Monroe/ Raycroft Road

The trail is well-maintained by the National Forest Service and features several campsites along its length. It becomes narrow in certain sections, particularly toward the northern end, where it intersects with cross-country ski and hiking…
Learn more about Prospect Mountain Trail

Narrow trail that meanders along the path of the Stamford Stream, dotted with private property. There is a parking area about halfway down to get out and stretch your legs, or park and head to…
Learn more about Dunville Hollow Road

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

Also known as Forest Road 278, this trail starts very easily and is scenic, but quickly turns into a challenge when you turn to head uphill. The track will require you to air down as…
Learn more about Middle Ridge Road

Somerset Trail (Forest Road 71) is a well-maintained, relatively smooth gravel road offering the same access and scenery as other routes in the area. Multiple pull-offs and campsites can be found along its length. Expect…
Learn more about Somerset Trail

Also known as Forest Road 83, this track follows the Deerfield River as it winds through scenic wetlands before gradually transitioning into a dense conifer forest. The setting changes noticeably along the route, offering a…
Learn more about Flood Dam Trail

Kelly Stand Road serves as the main artery through the heart of the Green Mountain National Forest. With numerous spur trails branching off along the way, there's something here for everyone to explore. You'll also…
Learn more about Kelly Stand Road

The trail consists of a broad gravel base that is regularly maintained. Drivers can expect a stable surface with minimal challenges. Logging operations are common in this area, so the road may be freshly plowed…
Learn more about Peasley Road

The trail consists of a broad gravel base that is regularly maintained by the state. Like other trails in this area, there is active logging occurring at all times of the year, so always keep…
Learn more about Cook Hill Road

The trail consists of a broad gravel base that is regularly maintained by the state. Be aware that active logging occurs at all times of the year in this area so always keep an eye…
Learn more about Partridge Run

Also known as Forest Road 86, this short but important trail provides access to several campsites, some of which are drier than others in the area. It's a narrow, out-and-back two-track that terminates at a…
Learn more about Smith Woods Trail

This is a loose stone and dirt road. This is a short section of road made up of loose stone and gravel. This road follows a river the whole way. There is nothing technical here;…
Learn more about Mill Hollow Road