Beginner Off-Road Trails
Near Millbrook, New York

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 a small pond/lake that one of the hiking trails leads to.
Learn more about Eastern Boundary Trail

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 small bridge. There are areas to pull over and park, and to go hiking.
Learn more about Rogue Harbor 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 to pull over and park to go hiking. Nothing technical, just a nice short ride.,
Learn more about Cutler 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 and park to go hiking. At about 4 miles in, this changes to a much more technical route. The ...
Learn more about Lundy Road

Mt Wilcox Road is the main loop that meanders through Beartown State Forest. The loop is 4.3 miles and climbs from 1,600 feet to 2,100 feet. The trail begins and ends off Benedict Pond Road. Halfway through the route from either direction is a short spur that breaks off and provides access to the su...
Learn more about Mount Wilcox Road

Sky Peak Road is a short connector between Beartown Mountain Road and Wilcox Mountain Road. The trail begins from Beartown and climbs from 1760 to 1900 feet in the short 0.7 miles of the trail over loose rock. The trail is well-graded in most sections, with some showing exposed rock. The trail ends...
Learn more about Sky Peak Road

Beartown Mountain Road winds its way through the northern section of Beartown State Forest. Beginning at route 102 and travelling south into the park, the gravel begins 2 miles in. The trail begins at an unlocked gate. Remnants of pavement that deteriorated over the years are still visible from t...
Learn more about Beartown Mountain Road

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 at the end as it is a dead end.
Learn more about Fire Tower Road

This short, unmaintained dirt road offers a rugged entryway into the 5,000-acre Naugatuck State Forest. Most of the trail is only one vehicle wide and runs directly alongside an active railroad, adding a unique backdrop to the drive. While brief, the route features deep ruts and significant mud pudd...
Learn more about Cold Springs 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 this peaceful path. While not much of a challenge for trucks or SUVs, cars should no...
Learn more about Old Macedonia Road

Blandford Road begins off of Schoolhouse Road in Tolland and heads west, ending just over the Granville line. Trail provides access to the southern portion of Amos Case Road as well as some other routes in the area. With two intersections along the route, stay right at the first and left at the seco...
Learn more about Blandford Road

This trail leads you to a lake at the end, where the old Shawanga Lodge used to stand. I didn't see any "no motorized vehicles beyond this point" or "no trespassing" signs until the end of the trail, where you hit a locked gate where the private property begins. Not much room at the end to turn arou...
Learn more about Vacant Lot Trail

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 fields to hardwood forests. While easily traveled by any car with moderate clearance, it is a bump...
Learn more about Deane Hill/Rossiter 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 is a one-lane trail with several spots to pull over. On rainy days, it will be a little slick, and some water will run down...
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 days, and some water will run down. There is nothing too technical here, and it is a one-lane trail with several spots to. Beautiful...
Learn more about Barnes Road

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; there are spots to pull over to let other vehicles go by.
Learn more about Mill Hollow 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 town road that is not maintained and goes through a beautiful area.
Learn more about Denman Mountain Rd

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 a higher-clearance vehicle is needed to avoid bottoming out. Multiple kayak and canoe launch sites do...
Learn more about Roaring Brook Road

Lower Tower Road is a short ride that leads to one of the nicest views in all of western MA. 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. From there, ...
Learn more about Lower Tower Road

Welcome to October Mountain State Forest, the largest state forest in MA. Country Road is the main entrance into the state forest. The gravel road is well-maintained and provides access to several areas of the park. Stop and enjoy the views of the wetlands to the west, or take a stop by the Appalac...
Learn more about Country Road

Mt Wilcox Road is the main loop that meanders through Beartown State Forest. The loop is 4.3 miles and climbs from 1,600 feet to 2,100 feet. The trail begins and ends off Benedict Pond Road. Halfway through the route from either direction is a short spur that breaks off and provides access to the su...
Learn more about Mount Wilcox Road

Sky Peak Road is a short connector between Beartown Mountain Road and Wilcox Mountain Road. The trail begins from Beartown and climbs from 1760 to 1900 feet in the short 0.7 miles of the trail over loose rock. The trail is well-graded in most sections, with some showing exposed rock. The trail ends...
Learn more about Sky Peak 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 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 smoother, especially when the ruts deepen, or rain turns things muddy. You’ll pa...
Learn more about Del Reeves Road

Mt Wilcox Road is the main loop that meanders through Beartown State Forest. The loop is 4.3 miles and climbs from 1,600 feet to 2,100 feet. The trail begins and ends off Benedict Pond Road. Halfway through the route from either direction is a short spur that breaks off and provides access to the su...
Learn more about Mount Wilcox Road

Sky Peak Road is a short connector between Beartown Mountain Road and Wilcox Mountain Road. The trail begins from Beartown and climbs from 1760 to 1900 feet in the short 0.7 miles of the trail over loose rock. The trail is well-graded in most sections, with some showing exposed rock. The trail ends...
Learn more about Sky Peak 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 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 smoother, especially when the ruts deepen, or rain turns things muddy. You’ll pa...
Learn more about Del Reeves Road