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runs
Jogging around Bennington offers access to diverse trail systems and natural attractions. The region is characterized by lush forests, rolling hills, and mountain views, providing varied terrain for running. Bennington features an extensive network of trails, including multi-use singletrack and woodland paths, suitable for different fitness levels. These running routes in Bennington Vermont traverse areas with significant elevation changes and scenic overlooks.
Last updated: May 12, 2026
3
runners
10.4km
01:27
340m
340m
This difficult 6.4-mile jogging loop on Crotched Mountain offers challenging rocky terrain and expansive views of Mount Monadnock.
1
runners
24.5km
02:32
130m
130m
Jog the Hillsborough Recreational Rail Trail, a difficult 15.2-mile route through varied terrain, historic sites, and scenic river views.

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4.32km
00:41
240m
240m
Jog the Bald Mountain Loop, a moderate 2.7-mile trail in dePierrefeu-Willard Pond Wildlife Sanctuary, featuring summit views and Willard Pon
2
runners
10.8km
01:13
220m
220m
Moderate run. Good fitness required. Mostly paved surfaces. Suitable for all skill levels.
2
runners
6.15km
00:45
150m
150m
Moderate run. Good fitness required. Mostly paved surfaces. Suitable for all skill levels.
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Popular around Bennington
Willard Pond is a 100 acre pond in the dePierrefeu-Willard Pond Wildlife Sanctuary. The pond is a habitat for many different types of wildlife, so it is a protected area that does not allow swimming or fishing. The path that runs along the banks gives you great, unobstructed views of the water.
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Great view from the top of Bald Mountain of the valley below and Crotched Mountain in the distance. It is a moderate hike to get to the top, but it is definitely worth the effort.
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This is a preserved area composed of swamps, streams, grassland, vernal pools and ledges, and is home to diverse fauna including: wild turkey, moose, whitetail deer, hawks, barred owl, snowshoe hare, beaver, mink; and many other wild animals. Being the biggest town forest preserved by Fracestown, it extends from Farrington Road and Route 136 on the south side of Crotched Mt. to East Road.
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Great view from the top of Crotched Mountain. During your run to the top, you will pass other view points into the valley, but the peak is definitely worth the effort as it gives you the best view in the area.
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Crotched Mountain offers many hiking trails from different slopes, traversing scenic viewpoints sitting in the “crotches” around the mountain, offering views of the woodland and cities around. At the summit, there is a cell tower which is not accessible by the trails. Here the first wind farm in the world was built in 1980, but the company went out of service and the 20 turbines were dismantled years ago. Crotched Mountain is also a popular ski station in New Hampshire.
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The Hillsborough Recreational Rail Trail is a great unpaved multiuse trail that follows the Contoocook River through rural landscapes. It is built on the old rail bed of the former Boston and Maine Railroad. You will see evidence of the old railway as you can still see the rails in some places and the path crosses several cross trestle bridges
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Bennington offers a diverse range of terrain for runners. You'll find everything from multi-use singletrack trails within the Bennington Area Trail System (BATS) to woodland paths, hilly options like those around Willow Park, and even sections of iconic long-distance trails such as the Appalachian Trail and Long Trail. Some routes, like the Crotched Mountain Summit East and West Trail Loop, feature significant elevation gains, while others, such as the Hillsborough Recreational Rail Trail, follow former railway lines offering longer distances with less elevation change.
Yes, Bennington provides running routes for various fitness levels. You can find moderate loops, such as the Bald Mountain Loop, which is 2.7 miles long, or more challenging routes with significant climbs like the Crotched Mountain Summit East and West Trail Loop, which has over 1,100 feet of elevation gain. The region's trail network ensures options for both casual joggers and experienced trail runners.
Bennington's running routes often pass by or lead to several natural attractions and landmarks. You can explore trails around Lake Shaftsbury State Park or Woodford State Park, which offer scenic loops around lakes. The Mile Around Woods in North Bennington provides woodland and pasture trails with far-reaching mountain views. For historical significance and panoramic vistas, the Bennington Battle Monument offers breathtaking views of the surrounding valleys and mountains.
Absolutely. Many routes in the Bennington area provide stunning views. For example, trails within the Bennington Area Trail System (BATS), like Zaphod's Run, lead to higher elevations on Mount Anthony, offering panoramic views of Bennington and the surrounding valley. The Harmon Hill Trail also provides significant climbs and stunning overlooks of the town, while the Mile Around Woods offers far-reaching mountain views, especially vibrant during fall foliage.
While specific 'family-friendly' designations can vary, trails around Lake Shaftsbury State Park, with its one-mile loop around the lake, or the relatively flat sections of the Hillsborough Recreational Rail Trail, could be suitable for families looking for less strenuous options. The Mile Around Woods also offers gentle woodland and pasture trails that are pleasant for all ages.
Many trails in the Bennington area are dog-friendly, but it's always best to check specific park or trail regulations before heading out. Generally, trails within the Bennington Area Trail System (BATS) and state parks like Lake Shaftsbury or Woodford State Park allow dogs, often requiring them to be on a leash. Always remember to clean up after your pet.
Yes, Bennington offers several circular running routes. The Bald Mountain Loop is a 2.7-mile trail that takes you through woodland and offers views from the summit. Additionally, Lake Shaftsbury State Park features a one-mile trail that loops around the lake, and Woodford State Park has a 2.7-mile trail around Adams Reservoir, both excellent options for a circular run.
Bennington offers beautiful running conditions throughout much of the year. Spring brings wildflowers, and fall is particularly stunning with vibrant foliage, making it a popular time for scenic runs. Summer provides lush green landscapes, though some trails might be more crowded. Winter running is also possible, especially on well-maintained paths, but conditions can vary with snow and ice, so appropriate gear is essential.
For beginners, routes with less elevation change are ideal. The Hillsborough Recreational Rail Trail, while long at 15.2 miles, follows a former railway line, making it relatively flat and suitable for those looking for an easier, longer run. The one-mile trail around Lake Shaftsbury State Park is also a gentle option, as are the woodland and pasture trails found in the Mile Around Woods.
Runners frequently praise Bennington for its diverse trail networks and stunning natural beauty. The region's lush forests, rolling hills, and mountain views provide a scenic backdrop for any run. Many appreciate the variety of terrain, from challenging mountain climbs to serene lakeside loops, and the opportunity to explore sections of famous trails like the Appalachian and Long Trails.
Yes, several running routes in Bennington feature water elements. Lake Shaftsbury State Park offers a pleasant one-mile trail around the lake, perfect for a refreshing run. Similarly, Woodford State Park has a 2.7-mile trail that winds around Adams Reservoir and crosses small streams, providing a tranquil running experience amidst evergreen forests. Lake Paran also has a nature trail along its woodlands.
Komoot currently features 3 running routes in the Bennington area, offering a variety of distances and difficulties. These include challenging mountain loops and longer rail trails, providing options for different preferences and fitness levels.


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