Routes

Planner

Features

Updates

App

Login or Signup

Get the App

Login or Signup

Routes
Cycling routes
United States
Vermont
Bennington County

South Shaftsbury

The best cycling routes around South Shaftsbury

5

riders

4

rides

Touring cycling routes around South Shaftsbury offer a blend of scenic beauty and varied terrain. The region is characterized by rolling hills, the expansive Green Mountains, and picturesque river valleys. Cyclists can expect a mix of open farmlands and dense forested areas, with routes often featuring significant elevation gains. This landscape provides diverse options, from flat sections on repurposed rail trails to more challenging paths within the Green Mountain National Forest.

Best touring cycling routes around South Shaftsbury

  • The most…

Last updated: July 12, 2026

2

riders

#1.

Bennington Battle Monument – Vermont Working Farm (Gravel Road) loop from Bennington

30.8km

02:26

530m

530m

Hard bike ride. Very good fitness required. Mostly paved surfaces. Suitable for all skill levels.

Navigate with device

Send to Phone

Save

Hard

1

riders

20.9km

01:16

200m

200m

This moderate 13.0-mile (20.9 km) bike loop from Bennington offers a delightful mix of rolling roads and wooded stretches, providing a classic Vermont touring cycling experience. As you pedal, you'll…

Moderate
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

Easy bike ride. Great for any fitness level. Mostly paved surfaces. Suitable for all skill levels.

Easy

This Bennington Battle Monument loop offers a challenging touring bicycle experience through Vermont's diverse landscapes, weaving between the Green Mountains and the Taconic Mountains. You'll encounter scenic valleys, working farms,…

Hard

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 South Shaftsbury

Hiking around South Shaftsbury

Road Cycling Routes around South Shaftsbury

Running Trails around South Shaftsbury

Tips from the Community

Alex
January 26, 2024, Bennington Battle Monument

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

Wonderful view from the monument into the distance.

Translated by Googleβ€’

0

0

come between 10 and 5 to see the top of the monument.

1

0

Frequently Asked Questions

How many touring cycling routes are available around South Shaftsbury?

There are 5 touring cycling routes available around South Shaftsbury. These routes offer a variety of distances and difficulties, from easy to difficult, catering to different cycling preferences.

Are there easy touring cycling routes suitable for beginners or families?

Yes, there is one easy touring cycling route available. The Bennington Battle Monument loop from Old Bennington is 18.7 km long with moderate elevation gain, making it a good option for those looking for a less strenuous ride. The region's varied terrain also includes repurposed rail trails which are generally flatter and suitable for families, though specific routes on these are not detailed here.

What are some options for longer touring cycling routes in the area?

For longer rides, consider the more challenging routes. The Bennington Battle Monument – Vermont Working Farm (Gravel Road) loop from Bennington is 38.2 km long with significant elevation gain, offering a substantial touring experience. Another option is the Bennington Battle Monument loop from Bennington, which covers 34.4 km with over 550 meters of ascent.

What kind of scenery can I expect on touring cycling routes near South Shaftsbury?

Touring cycling routes around South Shaftsbury offer diverse and picturesque scenery. You can expect to traverse scenic rural roads with views of the expansive Green Mountains, rolling hills, and river valleys. The landscape features a mix of open farmlands and dense forested areas. In autumn, the foliage provides a particularly stunning backdrop for cycling.

Are there any circular touring cycling routes available?

All 5 touring cycling routes listed for South Shaftsbury are circular loops, meaning you will start and end at the same point. This includes routes like the Bike loop from Bennington and the Bennington Battle Monument – Vermont Working Farm (Gravel Road) loop from Bennington.

What historical landmarks or attractions can I see along the routes?

Several routes incorporate notable landmarks. The Bennington Battle Monument is a prominent feature on multiple loops, including the Bennington Battle Monument loop from Old Bennington. You might also encounter historic covered bridges, such as the famous Silk Covered Bridge, which is a popular point of interest in the wider region.

When is the best time of year to go touring cycling in South Shaftsbury?

The best time for touring cycling in South Shaftsbury is generally from spring through autumn. The autumn foliage provides a particularly stunning backdrop. While winter cycling is possible, many routes may be covered in snow or ice, making them less suitable for touring bicycles.

What kind of terrain should I expect on these touring cycling routes?

The terrain around South Shaftsbury is characterized by constant rises and valleys, meaning most routes will involve significant elevation gains. You'll encounter a mix of paved rural roads, and some routes, like the Bennington Battle Monument – Vermont Working Farm (Gravel Road) loop from Bennington, specifically mention gravel sections. Expect varied surfaces and challenging climbs on many paths.

Where can I find parking for touring cycling routes in South Shaftsbury?

Many touring cycling routes in the South Shaftsbury area, particularly those originating from Bennington or Old Bennington, will have public parking available near their starting points. For specific parking information, it's advisable to check local resources or the komoot tour details for the exact starting location of your chosen route.

Are there challenging touring cycling routes for experienced cyclists?

Yes, there are several challenging options. Three of the five routes are rated as difficult, featuring significant distances and elevation gains. For example, the Bennington Battle Monument – Vermont Working Farm (Gravel Road) loop from Bennington covers 38.2 km with nearly 700 meters of ascent, providing a demanding ride for experienced touring cyclists.

Most popular routes around South Shaftsbury

Hiking around South Shaftsbury

Most popular attractions around South Shaftsbury

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 Cycling routes in other regions.

Lye Brook WildernessManchester CenterManchesterPownalStratton MountainEast DorsetPownal CenterNorth PownalOld BenningtonStamfordBenningtonGlastenbury WildernessNorth Bennington

Nearby adventure guides

Things to Do around North 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