Routes

Planner

Features

Updates

App

Login or Signup

Get the App

Login or Signup

Login or Signup

Routes
Road cycling routes
United States
Vermont

Bennington County

The best road cycling routes in Bennington County

4.7

(23)

1,048

riders

50

rides

Road cycling in Bennington County offers diverse terrain, situated between the Green Mountains and the Taconic Mountains. The region features a mix of challenging climbs, rolling roads, and scenic river valleys, including those of the Walloomsac and Battenkill rivers. Extensive woodlands and pastoral landscapes characterize many routes, providing varied backdrops for rides. Cyclists can expect a combination of paved and gravel surfaces, often passing by historic landmarks and working farms.

Best road cycling routes in Bennington County

  • The most popular…

Last updated: April 30, 2026

28

riders

#1.

Chiselville Covered Bridge loop from Manchester Center

37.2km

01:51

360m

360m

Moderate road ride. Good fitness required. Some segments of this route may be unpaved and difficult to ride.

Navigate with device

Send to Phone

Save

Moderate

Moderate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride.

Moderate
guide_signup
Let us show you the way with the komoot mobile app
With a free komoot account, you can easily find, customize, and navigate endless outdoor adventures.

Sign up for free

Moderate road ride. Good fitness required. Some segments of this route may be unpaved and difficult to ride.

Moderate

Moderate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride.

Moderate

Moderate road ride. Good fitness required. Some segments of this route may be unpaved and difficult to ride.

Moderate

Moderate road ride. Good fitness required. Some segments of this route may be unpaved and difficult to ride.

Moderate

Hard road ride. Very good fitness required. Some segments of this route may be unpaved and difficult to ride.

Hard

9

riders

47.9km

02:09

510m

510m

Moderate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride.

Moderate

9

riders

Hard road ride. Very good fitness required. Mostly well-paved surfaces and easy to ride.

Hard

4.0

(1)

11

riders

Moderate road ride. Good fitness required. Some segments of this route may be unpaved and difficult to ride.

Moderate
Sign up for free to see 41 more rides in Bennington County.

Get access to more routes and recommendations from other explorers.

Sign up for free

Already have an account?

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 County

Road Cycling Routes around Pownal

Road Cycling Routes around Pownal Center

Road Cycling Routes around North Pownal

Road Cycling Routes in Lye Brook Wilderness

Road Cycling Routes around East Dorset

Road Cycling Routes around Dorset

Road Cycling Routes around Manchester

Road Cycling Routes around Stamford

Road Cycling Routes around Manchester Center

Road Cycling Routes around Arlington

Other adventures in Bennington County

The Appalachian Trail — America's most iconic long-distance hike

Hiking Collection by

Jamie S.

Tips from the Community

Felix
June 20, 2025, Natural Bridge State Park Waterfalls

Probably more impressive to ride/drive up through McCauley Road. You can also access it from Natural Bridge or Hudson Brook Lane Road on foot or on a bike (which is what we did). White marble natural bridges/quarries are apparently not very common in the North America. Worth the detour if you are in North Adams.

0

0

This is a stunning covered bridge. It is also known as the East Arlington Covered Bridge. It was built in 1870 and spans over the Roaring Branch of the Batten Kill on Sunderland Hill Road in the town of Sunderland, Vermont. There is a sign on the bridge that states you will get fined $1 if you drive over the bridge faster than a walking man.

1

0

Natalie
February 6, 2024, Lyons Pond

Lyons Pond can be seen glistening between the tall pine trees. Many years ago, ice from the pond was stored in ice houses for use in food preservation during the summer. The ice was packed into the houses with sawdust and it was surprisingly effective. If done well, it could remain frozen for several years.

0

0

AverieOutside
February 6, 2024, Hapgood Pond

Hapgood Pond is a 12-acre pond that is 12 feet deep at its deepest point. This pond is within a recreation area of the same name. The recreation area has a campground, restrooms, picnic tables, and a swimming beach.

0

0

The Church of the Sacred Heart and St. Francis de Sales, located in Bennington, Vermont, holds a rich history dating back to its establishment. Serving as a spiritual cornerstone, the church's architectural and cultural significance draws interest. It stands as a testament to the community's enduring faith and heritage.

0

0

Alex
January 26, 2024, Silk Covered Bridge

The Silk Covered Bridge, part of Silk Road, spans the Walloomsac River connecting Bennington and North Bennington, Vermont. Constructed in 1840, this Town lattice truss bridge is one of three in the vicinity. Its historical significance led to its inclusion in the National Register of Historic Places in 1973.

0

0

This is a stunning covered bridge. It is also known as the East Arlington Covered Bridge. It was built in 1870 and spans over the Roaring Branch of the Batten Kill on Sunderland Hill Road in the town of Sunderland, Vermont. There is a sign on the bridge that states you will get fined $1 if you drive over the bridge faster than a walking man.

0

0

David Howells
January 20, 2024, Hoosic River

The beautiful Hoosic River runs through three states and is fed by streams from the Green Mountains of Vermont, the Taconics of New York and the lofty sides of Mount Greylock, the highest peak in Massachusetts (3,491 ft.). Its meandering journey travels 70 miles from where it begins at the Cheshire Reservoir in Massachusetts, to where it eventually enters the Hudson River at Stillwater, NY.

0

0

Frequently Asked Questions

What kind of terrain and difficulty can I expect on road cycling routes in Bennington County?

Bennington County offers a diverse range of terrain, situated between the Green Mountains and the Taconic Mountains. You'll find a mix of challenging climbs, rolling roads, and scenic river valleys. Routes often combine paved and gravel surfaces, passing through extensive woodlands and pastoral landscapes. Difficulty levels vary, with 8 easy routes, 29 moderate routes, and 14 difficult routes available.

Are there easy road cycling routes suitable for beginners in Bennington County?

Yes, Bennington County has several easy road cycling routes perfect for beginners. One such route is the Mill Pond – Trout Pond loop from Manchester, which is 19.7 miles (31.8 km) long and leads through woodlands and past serene ponds. There are 8 easy routes in total to explore.

What are some challenging road cycling routes for experienced riders in Bennington County?

For experienced riders seeking a challenge, Bennington County offers 14 difficult routes. A notable option is the Schoolhouse Lake – Schuylerville Yacht Basin loop from Red Mill on the Batten Kill. This route is 75.6 miles (121.7 km) long, features significant elevation gain, and traverses varied landscapes, typically taking over 6 hours to complete.

What natural features will I encounter on road cycling routes in Bennington County?

Road cycling routes in Bennington County are rich with natural beauty. You'll often ride through extensive woodlands, past serene bodies of water like Lake Paran and Lake Shaftsbury, and alongside river valleys such as the Walloomsac and Battenkill. The region is nestled between the Green Mountains and the Taconic Mountains, providing breathtaking views and diverse landscapes.

Are there any historic landmarks or attractions along the road cycling routes?

Yes, many road cycling routes in Bennington County incorporate charming historic landmarks. You can expect to pass by working farms and historic covered bridges, including the Chiselville, Silk Road, Paper Mill, and Burt Henry bridges. The Chiselville Covered Bridge loop from Manchester specifically highlights one of these iconic structures, the Chiselville Covered Bridge.

Where can I find scenic viewpoints while road cycling in Bennington County?

Bennington County offers numerous scenic viewpoints, thanks to its mountainous terrain and river valleys. Routes often provide sweeping valley views, especially in areas like the Mile-Around-Woods or trails within the Bennington Area Trail System (BATS) that access higher elevations. For a dedicated viewpoint, consider routes that pass near Lookout Rock or Mount Equinox and St. Bruno Scenic Viewing Center.

Are there family-friendly road cycling routes in Bennington County?

While specific 'family-friendly' designations for road cycling can vary, routes with less elevation gain and shorter distances are generally suitable. The Mill Pond – Trout Pond loop from Manchester is an easy 19.7-mile route that could be a good option for families. Additionally, the Bennington Area Trail System (BATS) offers multi-use trails like the Carriage Road, which are beginner-friendly and wind through historic areas.

Are there many loop road cycling routes available in Bennington County?

Yes, many of the road cycling routes in Bennington County are designed as loops, offering convenient starting and ending points. Examples include the Schoolhouse Lake – Schuylerville Yacht Basin loop from Red Mill on the Batten Kill, the Chiselville Covered Bridge loop from Manchester, and the Silk Covered Bridge loop from North Bennington.

When is the best time of year for road cycling in Bennington County?

The best time for road cycling in Bennington County is generally from spring through fall. The region is particularly stunning in the fall when the extensive woodlands display vibrant foliage. Warmer months offer pleasant conditions for exploring the diverse terrain, but it's always advisable to check local weather forecasts before heading out.

Is parking available near road cycling routes in Bennington County?

While specific parking details for every route are not listed, many routes in Bennington County start from towns or recreational areas where parking is typically available. For example, the Chiselville Covered Bridge loop starts from Manchester, a town with various parking options. It's recommended to check the starting point of your chosen route for specific parking information.

What do other road cyclists enjoy the most about road cycling in Bennington County?

The komoot community highly rates road cycling in Bennington County, with an average score of 4.5 stars from 4 reviews. Cyclists often praise the region's diverse terrain, the scenic beauty of its river valleys and woodlands, and the charm of historic covered bridges. The variety of routes, from easy loops to challenging climbs, is also a frequently appreciated aspect.

Are there any routes that pass by lakes or ponds in Bennington County?

Yes, several road cycling routes in Bennington County will take you past beautiful lakes and ponds. For instance, the South Village Pond – Emerald Lake loop from Mettawee River and the South Village Pond – Emerald Lake loop from Lye Brook Falls Trailhead both feature serene bodies of water. The Hapgood Pond – Lyons Pond loop from Hapgood Pond Recreation Area is another great option.

Most popular routes in Bennington County

Hiking in Bennington County

Most popular attractions in Bennington County

Places to see

Store rating

Get inspired with the komoot mobile app

With a free komoot account, you can easily find, customize, and navigate endless outdoor adventures.

or

Join komoot Now

Store rating

Didn’t find what you were looking for?

Check out more Road cycling routes throughout Bennington County below and find the perfect route in your destination.

Stratton MountainArlingtonGlastenbury WildernessLye Brook WildernessSouth ShaftsburyStamfordDorsetReadsboroManchesterBenningtonEast DorsetNorth BenningtonNorth PownalPownal CenterOld BenningtonManchester CenterPownal

Nearby adventure guides

Things to Do around Arlington

background

Get ready to conquer new peaks

Sign up for Free

Explore
RoutesRoute plannerFeaturesHikesMTB TrailsRoad cycling routesBikepackingSitemap
Download the app
Follow Us on Socials

© komoot GmbH

Privacy Policy