Beginner Off-Road Trails
Near Winchester Center, Connecticut

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

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

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

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

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

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 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. 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 vehicles...
Learn more about Lenox Whitney Place 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 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 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 a few small, off-camber sections to navigate. The trail opens up after...
Learn more about Shenipsit Trail System

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

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

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 bumps, ruts, and the occasional mud hole--especially after a good rain. ...
Learn more about Del Reeves & North Mulford Roads

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

This track is very overgrown. If you like your paint, don't go down it. It does open up after the beginning, but it's super tight to start with branches all over the sides and top of your rig. The cell service is decent, but the GPS gets a little confused at times. The majority of the track is dirt;...
Learn more about Sully's Way

Level 1, besides one water crossing, which I'd give a 2 for a 4x4, single track wide, mostly rough gravel, overgrown slightly, will cause some scraping on the paint, it's maintained a little bit with clearing trees that fell, starts in Stafford Springs, Connecticut then ends in Hampden Massachusetts...
Learn more about Hampden 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 some muddy spots and shallow puddles, typically less than 12 inches deep. The road is wide en...
Learn more about Gulf 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

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

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

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

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

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