Beginner Off-Road Trails Near Bogus Hill, Connecticut

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 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 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

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 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

This is an easy cruise through Meshomasic State Forest along an unmaintained, mostly dirt road with some gravel sections. While it's passable in almost any vehicle, I recommend something with off-road capability due to frequent…
Learn more about Del Reeves & North Mulford Roads

In order to access the trail system of the Cockaponset State Forest, Old Country Road is a very straightforward dirt and gravel entrance. The road allows for a smooth cruising experience through the forest and…
Learn more about Old Country Road

This mellow backroad route through Meshomasic State Forest follows a rough, mostly dirt track with a few gravel sections mixed in. It's doable in nearly any vehicle, but something with off-road durability makes the ride…
Learn more about Del Reeves Road

This is a loose gravel road, most of which is suitable for two vehicles. There is nothing technical on this road; it is just a nice, easy drive, with views of the streams and a…
Learn more about Rogue Harbor Road

The dirt and gravel Mottland Road to Jericho Road leads directly into the Cockaponset State Forest trail network. Enjoy a leisurely drive through the forest on this road, which also leads to several unmarked side…
Learn more about Mottlan - Jericho Road

This started out as a loose gravel, non-maintained 2-lane road, nothing technically. This follows a river where there are plenty of pull-offs to walk down to the river. Also, there are sections to pull over…
Learn more about Lundy Road

Serving as an entrance to the Cockaponset State Forest trail system, Filley Road is a very straightforward dirt and gravel path. The road allows for a smooth cruising experience through the forest and offers additional…
Learn more about Filley Road

This is a loose gravel road off of Lundy Road. Cross over a bridge and start climbing up a small hill. At the end turn around and head back to Lundy Road. There are sections…
Learn more about Cutler Road

This trail is a straightforward path; however, there are sections that have puddle crossings that range from six to ten inches in size and require some ground clearance. The majority of obstacles are very straightforward…
Learn more about Tower Hill Road to Spruce Ledge Road

This is a short trail off Lundy Road that is a one-lane road with limited pull-offs. Some small water/mud holes. There is a section to park at the end and go hiking. There is also…
Learn more about Eastern Boundary Trail

This is a short, loose gravel section of road. Nothing technical at all, is one lane, but has pull-offs. There is a small parking section at the end for hiking. Will have to turn around…
Learn more about Fire Tower Road

This easy dirt road cuts through Salmon River State Forest, offering a smooth ride with a few rockier sections--nothing a stock 2WD vehicle can't handle with a bit of care. After rainfall, you may encounter…
Learn more about Gulf 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

Like many dirt roads in Connecticut, this one winds through the Babcock Pond Wildlife Management Area, offering a fun and scenic ride. Expect a few deep mud holes--nothing a stock 4WD vehicle can't handle with…
Learn more about Miles Standish Road

This scenic trail winds through Shenipsit State Forest, offering a mix of challenging and easy terrain. Starting from Kibbe Road, expect some tight, narrow sections where pinstriping is likely for full-size trucks. There are also…
Learn more about Shenipsit Trail System

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

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

This trail is a public road that is not maintained. It is a mix of packed and loose gravel with a few sections of puddles and rocks. There is nothing too technical here, and it…
Learn more about Moore Hill Road

This trail is a public road that is not maintained. It is a mix of packed and loose gravel with a few sections of puddles and rocks. It will be a little slick on rainy…
Learn more about Barnes Road

This is a mix of packed and loose gravel. It is flat for the most part, nothing technical. There are several spots to pull over to let other vehicles go. The trail is a public…
Learn more about Denman Mountain Rd

This trail is a mix of packed and loose gravel. As you start to climb the hill, there are some sections that are washed out and have formed some deep ruts. When it rains, there…
Learn more about Wolf Brook Trail

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 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