Beginner Off-Road Trails Near New Haven, Connecticut

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…
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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

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

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…
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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

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 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

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 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…
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…
Learn more about Hampden 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…
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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

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 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

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…
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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…
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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…
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Baker Road starts with a "1" rated car-friendly mixed gravel and paved section. It becomes a "2" rated two-track when it crosses Quaddick Town Farm Road. Most people enter the trail here to avoid houses.…
Learn more about Baker & Cruff Roads

Center Trail is the longest trail in the Northwest Rhode Island Trail Network. It runs from Pulaski State Park on its West end (photos 1-3) to Olney Keach Road on its East end (photo 7).…
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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…
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Richardson Clearing Trail (photo five shows where it leaves Safari Trail) becomes Cold Spring Drive at an open gate (photo six). This trail provides access to Center Trail (photo seven) in the Northeast Rhode Island…
Learn more about Richardson Clearing Trail & Cold Spring Drive

This trail starts with a "1" rating until you pass the two houses (slowly please), then becomes an upper "3" rating as it is poorly maintained and often muddy until it enters Rhode Island which…
Learn more about Wakefield Pond & Silver Brook Roads

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

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 easy trail leads to the George Washington State Park Campground and continues through a gate at the North end that is only open when the campground is closed for the winter from November until…
Learn more about George Washington State Park Trail

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

Head down Onley Keach Road and begin once the pavement turns to dirt just after the houses. This trail is a dirt and gravel road. It will loosen your filings and shed parts from your…
Learn more about Olney Keach Road