4.8
(23)
71
riders
6
rides
Touring cycling routes around Bennington are set amidst the varied landscapes of the Green Mountains and Taconic Mountains in Vermont. The region features a mix of paved and gravel roads, with terrain ranging from river valleys to extensive woodlands. Cyclists encounter both rolling roads and sections with elevation gain, providing diverse riding experiences.
Last updated: June 28, 2026
5
riders
12.9km
00:48
100m
100m
An easy 8.0-mile touring cycling route around Standing Bear Lake, featuring scenic views and a floating boardwalk.
1
riders
22.9km
01:22
160m
160m
Cycle the 14.2-mile Flanagan Lake and Standing Bear Lake Loop in Omaha, a moderate touring route with scenic lake views and paved trails.

Sign up for free
4.6
(21)
26
riders
Easy bike ride. Great for any fitness level. Mostly paved surfaces. Suitable for all skill levels.
5.0
(2)
6
riders
33.3km
01:55
110m
110m
Easy bike ride. Great for any fitness level. Mostly paved surfaces. Suitable for all skill levels.
9
riders
Easy bike ride. Great for any fitness level. Mostly paved surfaces. Suitable for all skill levels.
Our route recommendations are based on thousands of hikes, rides, and runs completed by other people on komoot.
Start today with a free account
Your next adventure awaits.
Login or Signup
Popular around Bennington
This old railroad bridge reveals the origins of this stretch of trail: It was once part of the country's first transcontinental railroad.
0
0
This little neighborhood path has a nice paved path you can cycle along a tree-lined corridor.
0
0
The key feature of this little park is the community center to the south, but there's a little green space on the north side, too. This is a nice place to park if you're planning to cycle around Standing Bear Reservoir.
0
0
No path through Bluestem Prairie, but walking path is wide and lovely, just beautiful.
0
0
At this spot you cross a nice bridge over West Papio Creek. The water is lined with rushes and tall grasses, which makes the water sometimes a little hard to see from the side, but makes it a popular spot with birds and other wildlife. This is a nice place to slow down and keep an eye out for them!
0
0
Nice Trail with some cool art here and there and insight on the former use of the trail
0
0
The Cunningham Lake Pavilion is a great spot for a break if you are riding the Lake Cunningham Trail. It is a good place to get out of the sun on a hot day and enjoy the wonderful views of the lake.
1
0
The Standing Bear Lake Trail is an easy path that circles the lake with the same name. The trail is fully paved and gives you great views of the lake.
0
0
Bennington offers a diverse mix of terrain for touring cyclists. You'll find both paved and gravel roads, with routes traversing scenic river valleys, extensive woodlands, and rolling hills. While many routes feature significant elevation gain due to the Green Mountains and Taconic Mountains, there are also gentler options available.
Yes, Bennington has several easy touring cycling routes perfect for beginners. For instance, the Standing Bear Lake and Recreation Area Trail is an easy 8.0-mile route with minimal elevation gain. Another accessible option is the Flanagan Lake loop from Bennington, which is about 7.3 miles long.
The Bennington area is rich in natural beauty and historical landmarks. You can cycle past picturesque rivers like the Walloomsac and Battenkill, explore extensive woodlands, and discover charming covered bridges such as the Silk Covered Bridge. The iconic Bennington Battle Monument also offers panoramic views of the surrounding landscape. Specific routes might take you near Standing Bear Lake or Bluestem Prairie Preserve.
Many of the easy routes around Bennington are suitable for families. The Standing Bear Lake and Recreation Area Trail, with its minimal elevation and scenic lake views, is a great choice for a family outing. The Bennington Rail Trail also provides additional, generally flatter cycling opportunities.
Yes, several touring cycling routes in Bennington are designed as loops. A popular moderate option is the Flanagan Lake and Standing Bear Lake Loop, which connects two lake areas. Another circular route is the Tranquility Park loop from Bennington, offering a pleasant ride through parkland.
The best time for touring cycling in Bennington is generally from spring through fall. Spring offers lush greenery, while summer provides warm weather for exploring. However, the fall foliage season is particularly stunning, transforming the woodlands into a vibrant display of colors, making it a highly recommended time to visit for scenic rides.
The touring cycling routes around Bennington are highly regarded by the komoot community, with an average rating of 4.8 stars from over 7 reviews. Cyclists often praise the varied scenery, the mix of paved and gravel options, and the opportunity to explore both natural landscapes and historical sites.
Absolutely. The Bennington area features several routes that incorporate beautiful lakes and rivers. For example, the Flanagan Lake and Standing Bear Lake Loop connects two picturesque lake areas. You can also find routes that follow the Walloomsac and Battenkill Rivers, offering serene waterside views.
The touring cycling routes in Bennington vary in length to suit different preferences. You can find shorter, easy rides like the 8.0-mile Standing Bear Lake and Recreation Area Trail, or longer, moderate options such as the 14.2-mile Flanagan Lake and Standing Bear Lake Loop. There are also routes around 11-18 miles, like the Bluestem Prairie Preserve – West Papio Creek Bridge loop.
While the listed routes are primarily easy to moderate, the region's topography, nestled between the Green Mountains and Taconic Mountains, means that many areas offer significant elevation gain. Experienced riders can seek out longer routes or those with more pronounced climbs to find a challenge, often incorporating sections of the mountainous terrain for which Vermont is known.
While specific route regulations for dogs can vary, many outdoor areas in Bennington, including some multi-use trails and state parks, are dog-friendly. It's always best to check local signage or specific trail guidelines for the route you plan to take, and ensure your dog is on a leash and you clean up after them.
Parking availability varies by trailhead and route starting point. Many parks and trail access points in and around Bennington offer designated parking areas. For routes that start near urban or suburban areas, street parking might be an option, but it's always advisable to check specific parking instructions for your chosen route or destination.


Browse the best Cycling routes in other regions.