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

Bennington

The best road cycling routes around Bennington

5.0

(1)

55

riders

12

rides

Road cycling routes around Bennington, Vermont, traverse a varied landscape situated between the Green Mountains and the Taconic Mountains. The region features rolling hills, providing both sustained climbs and scenic descents. Routes often follow rivers like the Walloomsac and pass through woodlands, offering shaded sections and views of natural features. This topography creates diverse road cycling experiences for different skill levels.

Best road cycling routes around Bennington

  • The most popular road cycling route is Silk Covered Bridge loop from North…

Last updated: May 17, 2026

11

riders

#1.

Silk Covered Bridge – Bingham Hill loop from North Bennington

53.3km

02:28

580m

580m

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

9

riders

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

Hard
guide_signup
Let us show you the way with the komoot mobile app
With aΒ 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

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

Hard

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 8 more rides around Bennington.

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

Hiking around Bennington

Running Trails around Bennington

Cycling around Bennington

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

Alex
February 8, 2024, 1753 House

The 1753 House stands as a faithful reproduction of a settler's home from 1753 in The Berkshires. Situated in Field Park at Williamstown's west end, it was built by volunteers in 1953 to commemorate the town's Bicentennial. Early settlers in the Hoosac Valley, including Williamstown and North Adams, were obligated by contract to construct a house of specific dimensions and clear a designated amount of land to secure their lot. You can see the house from the roadside.

0

0

Alex
January 31, 2024, Thurber Pond

Cycling on this good quality road next to Thurber Pond is a joy with the pond directly in view. Keep your eyes peeled for the various pond life and birds that live around it.

0

0

The Bennington Battle Monument, erected in 1891, commemorates the Revolutionary War's Battle of Bennington in Vermont. Standing at 306 feet, it symbolizes the victory against British forces. Funded by patriotic citizens, the monument is a testament to the community's dedication to preserving and honoring its historical legacy.

0

0

Established in 1762, The First Congregational Church of Bennington, or Old First Church, boasts a rich history in Old Bennington, Vermont. The present meeting house, erected in 1805, stands as a stellar representation of Federal period religious architecture in the state. Recognized for its historical significance, it earned a spot on the National Register of Historic Places in 1973.

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

The Cold Spring Preserve borders the southern grounds of The Clark Art Institute, a well known local art museum with an impressive collection of 19th-century French Impressionist and Academic paintings and beautiful grounds. This is a nice place to slow down as you ride to admire the views and look out for wildlife.

0

0

Frequently Asked Questions

What kind of terrain can I expect on road cycling routes around Bennington?

Road cycling routes in Bennington, Vermont, offer a diverse terrain characterized by rolling hills and mountain views, situated between the Green Mountains and the Taconic Mountains. You'll find sustained climbs leading to panoramic vistas, as well as scenic descents. Many routes also meander through woodlands, providing shaded sections, and often follow rivers like the Walloomsac, offering tranquil scenery.

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

Yes, Bennington offers routes suitable for various skill levels, including easier options. While many routes feature rolling hills, there is at least one easy route available. For a generally flatter and accessible option, the Bennington Rail Trail caters to cyclists of all ages and abilities, though specific komoot routes on it aren't detailed here.

How many road cycling routes are available in the Bennington area?

There are over 10 road cycling routes around Bennington detailed in komoot, offering a variety of experiences for different skill levels. These include routes ranging from moderate to difficult, showcasing the region's diverse landscape.

What are some of the longer or more challenging road cycling routes in Bennington?

For those seeking a challenge, Bennington offers several difficult routes. One notable option is the Hoosic River loop from Bennington, a difficult 51.1-mile (82.2 km) path that follows the Hoosic River and provides views of the surrounding mountain ranges. Another challenging ride is the Bennington Battle Monument – Cold Spring Preserve loop from Bennington, which covers 72.4 miles (72.4 km) with significant elevation gain.

What historical landmarks or natural features can I see along the road cycling routes?

Bennington's road cycling routes often pass by significant historical landmarks and natural features. You can cycle past historic covered bridges like the Silk Covered Bridge. Routes may also lead to or offer views of the Bennington Battle Monument, which commemorates a Revolutionary War battle and provides expansive views. The region's natural beauty includes lakes such as Lake Paran and Lake Shaftsbury, and the Walloomsac River, which offer tranquil scenery.

Are there any routes that incorporate Bennington's famous covered bridges?

Yes, several routes are designed to feature the historic covered bridges. A popular choice is the Silk Covered Bridge loop from North Bennington, a 33.6-mile (54.1 km) trail that specifically incorporates these architectural gems. Another option is the Bingham Hill – Silk Covered Bridge loop from Shaftsbury, which also passes a covered bridge.

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

The best time for road cycling in Bennington is generally from spring through fall. Autumn is particularly spectacular, with vibrant foliage displays as routes meander through wooded areas. The cooler temperatures and stunning colors make for a memorable cycling experience. Summer offers warm weather and lush greenery, while spring brings fresh blooms.

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

Road cyclists often praise Bennington for its blend of natural beauty, varied terrain, and historic charm. The opportunity to combine physical activity with historical appreciation, such as cycling past covered bridges and historic sites, is a highlight. The region's rolling hills and mountain views provide engaging rides, and the active local cycling community adds to its appeal.

Are there any routes that follow rivers or lakes?

Yes, many routes in the Bennington area incorporate scenic waterways. For instance, the Hoosic River loop from Bennington directly follows the Hoosic River, offering picturesque views. Other routes may pass by tranquil bodies of water like Lake Paran and Lake Shaftsbury, providing serene landscapes.

Where can I find parking for road cycling routes in Bennington?

While specific parking locations for each trailhead are not detailed here, many routes around Bennington, North Bennington, and Shaftsbury typically start from areas where public parking is available. It's advisable to check the starting point of your chosen komoot route for specific parking recommendations or local town parking options.

Are there any routes that offer panoramic viewpoints?

Yes, the topography around Bennington, with its rolling hills and proximity to the Green and Taconic Mountains, means many routes offer opportunities for panoramic views. Sustained climbs into areas like Stamford and Savoy can lead to expansive vistas. The Bennington Battle Monument itself offers breathtaking views from its observation deck, and routes designed to pass by it will provide similar scenic rewards.

Most popular routes around Bennington

Hiking around Bennington

Most popular attractions around Bennington

Places to see

Store rating

Get inspired with the komoot mobile app

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

or

Join komoot Now

Store rating

Explore more

Browse the best Road cycling routes in other regions.

PownalPownal CenterNorth PownalDorsetEast DorsetLye Brook WildernessManchesterStamfordManchester CenterArlingtonOld BenningtonSouth ShaftsburyNorth BenningtonGlastenbury WildernessStratton MountainReadsboro

Nearby adventure guides

Things to Do around Old Bennington

background

Get ready to conquer new peaks

Sign up for Free

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

Β© komoot GmbH

Privacy Policy