4.0
(2)
15
riders
4
rides
Road cycling routes around Bennington traverse an area characterized by rolling hills, dense forests, and scenic river valleys. The landscape features a mix of paved country roads and routes that often pass by historic covered bridges. Elevation changes are moderate, providing varied terrain for road cyclists.
Last updated: May 21, 2026
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.

Sign up for free
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.
2
riders
45.1km
02:00
440m
440m
Moderate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride.
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
The Crotched Mountain Road surrounds the Francestown forest and takes you on an enjoyable ride below the canopy.
0
0
This old covered bridge spans the Contoocook River and gives a lovely view of the river and Powdermill Pond Wildlife Management Area around the water. The area is particularly beautiful in Autumn when the trees leaves change to amber and crimson colors.
0
0
This quiet lake and its beach are perfect for taking a rest off of the bike. With a lovely sandy beach to get into the water, the lake is perfect for a cool off on a summers day.
0
0
This quiet road has lovely views of Contocook River, and a slightly rickety old bridge spanning it. During Autumn the forest colours really pop here, turning a range of crimson and amber hues.
0
0
Harrisville is a charming small town centered around a historic 19th-century industrial mill complex. The town is frequently photographed as an example of picturesque New England.
0
0
The Crotched mountain road surrounds the Francestown town forest and takes you on an enjoyable ride below the canopy.
0
0
Road cycling routes around Bennington feature a landscape of rolling hills, dense forests, and scenic river valleys. You'll encounter a mix of paved country roads, often passing historic covered bridges. The elevation changes are generally moderate, offering varied terrain suitable for most road cyclists.
The routes in Bennington are primarily categorized as moderate difficulty, offering varied terrain with rolling hills. While there aren't specific 'easy' routes listed, the moderate elevation changes make them accessible for cyclists with some experience. For a good introduction, consider the Forest Road covered bridge loop from Fisher Hill Town Forest, which is a popular choice.
Most road cycling routes around Bennington range from approximately 22 to 28 miles (35 to 45 km) in length. A typical ride, like the Forest Road covered bridge loop from Hancock, takes about 1 hour 30 minutes to 2 hours to complete, depending on your pace.
The best time for road biking in Bennington is typically from late spring through early autumn (May to October). During these months, the weather is generally pleasant, and the scenery, especially the fall foliage, is spectacular. Winter cycling is possible but requires appropriate gear and caution due to snow and ice.
While the routes are generally moderate, the paved country roads and scenic nature of Bennington can be enjoyable for families with older children who are comfortable with longer distances and some elevation changes. The routes often wind through forested areas, providing a pleasant environment away from heavy traffic.
A defining feature of road cycling in Bennington is the presence of historic covered bridges. Many routes, such as the Forest Road covered bridge loop from Greenfield, specifically highlight these charming landmarks. You'll also enjoy forested roads and views of river valleys.
Yes, many of the road cycling routes in Bennington are designed as loops, offering a continuous scenic journey without retracing your path. Examples include the various 'Forest Road covered bridge loop' options and the Francestown forest – Antrim Road loop from Fleck Conservation Area.
The road cycling routes in Bennington are highly rated by the komoot community, with an average score of 4.0 stars. Cyclists often praise the quiet forested roads, the charm of the covered bridges, and the varied, yet manageable, terrain.
Many of Bennington's road cycling routes utilize paved country roads that typically have lower traffic volumes compared to main highways. Routes winding through forested areas, like the Lake beach – Harrisville loop from ConVal Regional High School, often provide a more serene cycling experience.
There are several road cycling routes available around Bennington, offering various options for exploring the region's unique landscape. Komoot currently lists four distinct routes in this guide, all of moderate difficulty.


Browse the best Road cycling routes in other regions.