
18
runners
5
runs
Jogging around Old Bennington offers routes through a landscape characterized by rolling hills and historic streets, with views of the surrounding Green Mountains. The area provides a blend of natural features and historical landmarks, creating varied terrain for runners. Routes often feature elevation changes, contributing to a more challenging experience. This topography ensures diverse running opportunities within the region.
Last updated: July 4, 2026
5
runners
7.43km
00:47
80m
80m
Moderate run. Good fitness required. Mostly paved surfaces. Suitable for all skill levels.
5
runners
8.70km
00:55
80m
80m
Moderate run. Good fitness required. Mostly paved surfaces. Suitable for all skill levels.

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3
runners
9.47km
01:00
110m
110m
Moderate run. Good fitness required. Mostly paved surfaces. Suitable for all skill levels.
3
runners
8.38km
00:53
100m
100m
Moderate run. Good fitness required. Mostly paved surfaces. Suitable for all skill levels.
2
runners
7.49km
00:51
70m
70m
Moderate run. Good fitness required. Mostly paved surfaces. Suitable for all skill levels.
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Popular around Old Bennington
Lake Paran is an excellent spot to take a break along your ride. Considered to be the best lake in the area with the cleanest water, it certainly makes a great spot to have a mid ride dip or refuel.
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There are 5 dedicated running routes around Old Bennington featured in this guide. These routes offer a variety of experiences through the region's historic streets and natural landscapes.
Jogging routes in Old Bennington are characterized by rolling hills and historic streets, offering views of the surrounding Green Mountains. You can expect varied terrain with natural elevation changes, providing a rewarding experience for runners.
The routes listed in this guide are generally classified as moderate in difficulty. While there are no routes specifically marked as 'easy', the varied terrain allows for different paces. For a less strenuous option, consider the grounds around the Bennington Battle Monument or the George Aiken Wildflower Trail for a lighter jog or walk.
Many running routes in Old Bennington pass by significant historical landmarks and natural features. You might encounter the towering Bennington Battle Monument, the historic Old First Church, or the picturesque Monument Avenue with its historic homes. The Running loop from Old Bennington specifically leads through historic streets and past local landmarks.
Yes, Old Bennington's elevated position provides many opportunities for scenic views. The grounds around the Bennington Battle Monument offer breathtaking panoramic views of Vermont, New Hampshire, and New York. Many routes naturally feature expansive views of the picturesque Vermont countryside and the Green Mountains due to the region's rolling hills.
Yes, all the running routes highlighted in this guide are circular loops. For example, you can enjoy the Running loop from North Bennington or the Running loop from Henry House, both designed for a continuous running experience.
The running trails in Old Bennington vary in length, generally ranging from approximately 4.6 miles (7.4 km) to 5.9 miles (9.5 km). For instance, the Lake Paran loop from North Bennington is about 4.6 miles, while the Running loop from Burt Henry Covered Bridge is around 5.2 miles.
While specific dog-friendly designations for each route are not provided, many outdoor areas in Vermont, including trails within the Bennington Area Trail System (BATS), generally welcome leashed dogs. It's always recommended to check local regulations for specific trails or parks before heading out with your pet.
For families looking for a more relaxed experience, the George Aiken Wildflower Trail near the Bennington Museum offers a lovely, shorter woodland garden trail. The grounds around the Old First Church and Cemetery also provide a serene environment for a walk or light jog suitable for families.
Many key areas in Old Bennington offer convenient parking. For example, the Bennington Battle Monument area provides space for visitors, and parking is generally available near historic sites and trailheads. Monument Avenue itself is easily accessible for those looking to jog along its scenic stretch.
Old Bennington is particularly stunning in the fall, with beautiful foliage along routes like Monument Avenue. Spring and summer also offer pleasant conditions for running, with lush greenery. Winter running is possible, but conditions may vary, requiring appropriate gear for snow and ice.
Yes, the region is known for its charming covered bridges. The Running loop from Burt Henry Covered Bridge specifically incorporates a visit to the Burt Henry Covered Bridge, offering a picturesque element to your run. You might also encounter the Silk Covered Bridge in the wider area.


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