Bennington is a region in southwestern Vermont, nestled within the Green Mountains. Its diverse landscape features prominent peaks like Mount Anthony, the expansive Valley of Vermont, and numerous lakes and wetlands, providing varied terrain for outdoor pursuits. The area is well-suited for several sports like jogging, touring cycling, hiking, and road cycling, offering a mix of challenging climbs and scenic, gentler paths.
Bennington offers numerous routes for outdoor activities across several sports like jogging, touring…
22
Routes
4.5
(4)
Average rating
49
People visited

5
hikers
2.32km
00:47
120m
110m
Easy hike. Great for any fitness level. Easily-accessible paths. Suitable for all skill levels.

5.0
(1)
4
hikers
6.33km
02:07
300m
300m
Moderate hike. Good fitness required. Easily-accessible paths. Suitable for all skill levels.

3
hikers
5.54km
01:29
60m
60m
Easy hike. Great for any fitness level. Easily-accessible paths. Suitable for all skill levels.

4
hikers
5.99km
01:45
150m
150m
Easy hike. Great for any fitness level. Easily-accessible paths. Suitable for all skill levels.
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3
runners
10.4km
01:27
340m
340m
Hard run. Very good fitness required. Mostly paved surfaces. Suitable for all skill levels.

1
runners
24.5km
02:32
130m
130m
Hard run. Very good fitness required. Mostly paved surfaces. Suitable for all skill levels.

4.32km
00:41
240m
240m
Moderate run. Good fitness required. Mostly paved surfaces. Suitable for all skill levels.

2
runners
10.8km
01:13
220m
220m
Moderate run. Good fitness required. Mostly paved surfaces. Suitable for all skill levels.
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19.6km
01:28
90m
90m
Easy bike ride. Great for any fitness level. Mostly paved surfaces. Suitable for all skill levels.

44.0km
03:01
500m
500m
Hard bike ride. Very good fitness required. Mostly paved surfaces. Suitable for all skill levels.

34.7km
02:51
480m
480m
Hard bike ride. Very good fitness required. Some segments of this route may be unpaved and difficult to ride.

3
riders
41.8km
03:19
530m
530m
Hard bike ride. Very good fitness required. Mostly paved surfaces. Suitable for all skill levels.
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4.0
(1)
3
riders
35.2km
01:37
370m
370m
Moderate road ride. Good fitness required. Some segments of this route may be unpaved and difficult to ride.

4.0
(1)
3
riders
35.5km
01:34
370m
370m
Moderate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride.

3
riders
38.2km
01:47
440m
440m
Moderate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride.

2
riders
43.1km
01:59
480m
480m
Moderate road ride. Good fitness required. Some segments of this route may be unpaved and difficult to ride.
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Bennington offers a variety of outdoor activities including jogging, hiking, touring cycling, and road cycling. Other options include mountain biking, swimming, fishing, canoeing, bird watching, cross-country skiing, snowshoeing, and snowmobiling. The region provides diverse terrain for all skill levels.
The Bennington Area Trail System (BATS) offers over 12 miles (19 km) of interconnected trails suitable for jogging, such as "Hops & Vines" and "Zaphod's Run." The Mile-Around Woods and the Robert Frost Trail also provide popular walking and running paths. For more details, refer to the Running Trails around Bennington guide.
Yes, sections of the Appalachian and Long Trails pass through the Bennington area, offering more challenging experiences. The Harmon Hill Trail is a popular day hike providing significant elevation gain and overlooks of Bennington. Woodford State Park also features hiking opportunities.
Bennington offers diverse cycling options, including mountain biking on the Bennington Area Trail System (BATS). The Bennington Rail Trail is suitable for cyclists of all ages, and scenic road cycling routes are available throughout the Green Mountains. Explore options in the Cycling around Bennington and Road Cycling Routes around Bennington guides.
Yes, trails like the Bennington Rail Trail are suitable for families and cyclists of all ages. The Mile-Around Woods and the Robert Frost Trail also offer gentler paths for walking. State parks such as Lake Shaftsbury State Park provide accessible nature trails.
Trails in Bennington offer views of prominent natural features such as Mount Anthony and the Green Mountains. The Valley of Vermont provides distant vistas framed by the Taconic and Green Mountains. Wetlands and beaver dams are visible along paths in Greenbergs Headwaters Park.
Many trails in the Bennington area are dog-friendly, but specific regulations can vary by location or park. It is advisable to check local signage or park websites for rules regarding pets, including leash requirements. Always practice responsible pet ownership.
Komoot offers several guides for Bennington, including Running Trails around Bennington, Cycling around Bennington, Hiking around Bennington, and Road Cycling Routes around Bennington. These guides provide detailed route information and user contributions.
Bennington is a well-regarded destination on komoot, with more than 75 visitors having shared their experiences. The routes in the region have an average rating of 4.67 out of 5 stars, indicating a high level of satisfaction among users.
For official tourism information about Bennington, visit VermontBeginsHere.com. The Downtown Visitor Center of Better Bennington Corporation can be reached at (802) 442-5758 for local inquiries.
Yes, Bennington offers various winter activities. The area is popular for cross-country skiing and snowshoeing, with Prospect Mountain hosting competitions. The V.A.S.T. snowmobile trail network also draws visitors from across New England.
The Bennington Area Trail System (BATS) is a network of over 12 miles (19 km) of interconnected trails. It is designed for multiple uses, including hiking, running, and mountain biking, offering scenic views of the valley and the Bennington Battle Monument.

