4.7
(3)
14
hikers
4
hikes
Hiking trails in Chestnut Woods State Forest offer an untamed experience across more than 800 acres along the New York and Vermont border. The forest features open hardwood forests and pine plantations, with an extensive network of former logging roads serving as informal trails. Remnants of historic stone walls can be found on higher ridges, and streams with small cascades add to the scenic beauty. From elevated points, screened views of rolling farmland and Shaftsbury Hollow are visible.
Last updated: May 2, 2026
4.0
(1)
1
hikers
4.92km
01:34
200m
200m
Easy hike. Great for any fitness level. Easily-accessible paths. Suitable for all skill levels.
5.0
(1)
4
hikers
3.49km
00:56
40m
40m
Easy hike. Great for any fitness level. Easily-accessible paths. Suitable for all skill levels.

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4
hikers
2.56km
00:41
30m
30m
Easy hike. Great for any fitness level. Easily-accessible paths. Suitable for all skill levels.
2
hikers
2.51km
00:38
10m
10m
Easy hike. Great for any fitness level. Easily-accessible paths. Suitable for all skill levels.
5.0
(1)
2
hikers
2.56km
00:39
10m
10m
Easy hike. Great for any fitness level. Easily-accessible paths. Suitable for all skill levels.
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Popular around Chestnut Woods State Forest
The Carriage Road is how most begin (and often end as well) their hike in the scenic, pastoral Mile-Around-Woods area. This bucolic segment of trail is west of the Park-McCullough Historic Governor's Mansion and follows a treed, old carriage road through some farm fields. This section of the Mile-Around-Woods is particurlaly stunning in the fall when the leaves are changing from green to bright hues of orange, yellow, and red.
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The Ledges is a clear, scenic spot in the from which you can see Mount Anthony, North Bennington, and the surrounding area across open fields. This is a great place to snap some photos of this classic New England vista as you amble around the beautiful Mile-Around-Woods area.
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Chestnut Woods State Forest offers a more untamed and solitary hiking experience. While there are no officially designated trails, you'll find an extensive network of former logging roads that are perfect for exploration. These informal paths wind through open hardwood forests and picturesque pine plantations, providing a quiet connection with nature away from more manicured routes.
Yes, all the routes we feature in Chestnut Woods State Forest are rated as easy. For example, you could try the Mile-Around Woods Trail, which is about 3.5 km long with minimal elevation gain, or the slightly shorter The Mile-Around Woods at 2.6 km.
Yes, Chestnut Woods State Forest is generally dog-friendly. The informal network of logging roads provides ample space for you and your canine companion to explore. Always ensure your dog is under control, and be mindful of wildlife in the area.
Yes, several of the routes in Chestnut Woods State Forest are circular, allowing you to start and end at the same point. A good option is the Battle Loop and Valley View Trail, which is a 4.9 km loop with some moderate elevation changes, offering varied scenery.
While hiking in Chestnut Woods State Forest, you can discover diverse natural attributes. Keep an eye out for remarkably open hardwood forests and serene pine plantations. You might also encounter a "pretty stream" with numerous "tiny cascades" mentioned by previous hikers. High on the ridge, you can find historic stone walls, remnants of past human activity, and from higher elevations, screened views of rolling farmland in White Creek and North Hoosic, as well as vistas over Shaftsbury Hollow.
Yes, primitive camping is permitted in Chestnut Woods State Forest, offering an immersive overnight experience. However, specific regulations regarding distance from water bodies, roads, or trails must be followed. It's always a good idea to check with local authorities for the most current guidelines before planning your trip.
Chestnut Woods State Forest offers unique experiences throughout the year. Spring brings fresh greenery, while summer provides lush shade. Autumn is particularly scenic with vibrant fall foliage. The informal logging roads are also suitable for winter activities like snowshoeing and cross-country skiing, offering a quiet, snowy landscape.
Chestnut Woods State Forest is teeming with wildlife, making it an excellent spot for nature observation. You might spot furbearers, game species like wild turkey and ruffed grouse, eastern coyotes, and a variety of songbirds, hawks, owls, mice, woodchucks, and porcupines. This rich biodiversity enhances the outdoor experience.
The routes we feature in Chestnut Woods State Forest are all rated as easy, with the most significant elevation gain being around 200 meters on the Battle Loop and Valley View Trail. The terrain primarily consists of former logging roads, which are generally manageable, though they can be uneven or muddy depending on weather conditions.
The area is highly rated by the komoot community, with an average score of 4.7 out of 5 stars. Reviewers often praise the forest's quiet solitude, the natural beauty of its open woodlands and streams, and the opportunity for an untamed outdoor experience away from crowded, formal trails.
While specific designated parking areas may vary, the informal nature of Chestnut Woods State Forest often means parking is available at trailheads or along the access roads to the former logging routes. It's advisable to check local regulations and signage upon arrival to ensure proper parking.


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