Routes

Planner

Features

Updates

App

Login or Signup

Get the App

Login or Signup

Login or Signup

Routes
Cycling routes
United States
Massachusetts

Berkshire County

The best cycling routes in Berkshire County

4.6

(25)

468

riders

66

rides

Touring cycling in Berkshire County offers routes through a landscape characterized by rolling hills, tranquil valleys, and lush forests in western Massachusetts. The region features mountain views from the Taconic Range and the Housatonic River Valley, providing diverse terrain for cyclists. Numerous lakes and rivers, such as Onota Lake and the Housatonic River, add to the scenic beauty of many routes. Forests and parks like Pittsfield State Forest also contain multi-use trails.

Best touring cycling routes in Berkshire County

  • The most popular touring cycling route is Ashuwillticook Rail Trail, a 27.2 miles (43.8 km) trail that takes 2 hours 29 minutes to complete. This paved rail trail offers gentle terrain and scenic views of the Hoosic River Valley.
  • Another top favourite among local touring cyclists is Ashuwillticook Rail Trail Head loop from Lanesborough, a moderate 26.1 miles (42.0 km) path. This route provides a loop experience of the rail trail, starting and ending near Lanesborough.
  • Local touring cyclists also love the Ashuwillticook Rail Trail Head loop from North Adams, a 19.9 miles (32.0 km) trail leading through the Hoosic River Valley, often completed in about 1 hour 51 minutes.
  • Touring cycling in Berkshire County is defined by rolling hills, tranquil valleys, and scenic rail trails. The network offers options for different ability levels, from easy paved paths to more challenging routes with significant elevation changes.
  • The routes in Berkshire County are highly rated by the komoot community with an average score of 4.6 stars from more than 20 reviews. More than 400 touring cyclists have used komoot to explore Berkshire County's varied terrain.

Last updated: April 24, 2026

5.0

(9)

103

riders

#1.

Ashuwillticook Rail Trail

43.8km

02:30

140m

140m

Embark on a touring bicycle adventure along the Ashuwillticook Rail Trail, a moderate 27.2 miles (43.8 km) route that follows a former railroad corridor. You will enjoy a smooth, level ride, gaining 453 feet (138 metres) in elevation over approximately 2 hours and 29 minutes. As you cycle, the trail winds through lush forested areas and wetlands, offering serene views of the Hoosic River Valley. Keep an eye out for glimpses of Mount Greylock in the distance and the tranquil waters of the Cheshire Reservoir. This path provides a peaceful escape into nature, perfect for a relaxed ride.

Planning your trip to the Ashuwillticook Rail Trail is straightforward, with several convenient access points. You will find seasonal restrooms available at key trailheads, including the Adams Visitor Center and the historic Boston & Albany Railroad Station in Cheshire. The route is well-maintained, featuring benches and picnic tables along the way for rest stops. This trail is also wheelchair accessible and welcomes dogs, making it a versatile option for many visitors.

The Ashuwillticook Rail Trail is notable for its transformation from a bustling railroad line into a scenic recreational path. This unique history allows you to traverse the landscape on a level grade, offering an intimate perspective of the Berkshire region's natural beauty. The wetlands and forested sections provide excellent opportunities for wildlife spotting, from various bird species to turtles. In autumn, the changing leaves create a particularly vibrant and memorable backdrop for your ride.

Navigate with device

Send to Phone

Save

Moderate

Moderate bike ride. Good fitness required. Mostly paved surfaces. Suitable for all skill levels.

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

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

Hard

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

Hard
Sign up for free to see 62 more rides in Berkshire 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 Berkshire County

Cycling around North Adams

Cycling around Pittsfield

Cycling in Pittsfield State Forest

Cycling in Balance Rock State Park

Cycling around Adams

Cycling in Bates Memorial State Park

Cycling in October Mountain State Forest

Cycling in Florida State Forest

Cycling in Savoy Mountain State Forest

Cycling in Natural Bridge State Park

Other adventures in Berkshire County

The Appalachian Trail β€” America's most iconic long-distance hike

Hiking Collection by

Jamie S.

Tips from the Community

ScottKane
August 31, 2025, Ashuwillticook Rail Trail

This is the most beautiful rail trail in Massachusetts hands down.

0

0

A great monument with a magnificent view once you have conquered the stairs. Tip: hike to the summit!

Translated by Googleβ€’

0

0

Converted from an old railroad track, the Ashuwillticook Rail Trail is now a 10 foot wide, 14.2 mile, paved multi use trail meandering along the Cheshire Reservoir while offering sublime views of Mt. Greylock.

0

0

Located just north of Adams, the Ashuwillticook Rail Trail Head sets a lovely tone for the rest of your ride along the trail, perfectly smooth and easy to use for families.

0

0

David Howells
February 9, 2024, Fitch Overlook

Fitch Overlook is located on Notch Road at an elevation of 2,850 feet, just below Mount Fitch itself, at Mount Greylock State Reservation. It is not a large overlook by any means, but it has great views out over towards Mount Prospect and Stony Ledge.

1

0

Here's the Trail Head of the Ashuwillticook Rail Trail. The trail is perfectly smooth and easy to use for families.

0

0

This is the highest point in Massachusetts. At the summit of Mount Greylock you will find the Veterans War Memorial Tower. The 92ft high tower stands as a beacon for peace, to honour those who died during World War I. You can even walk up the inside of the tower for even better views of the surrounding area.

1

0

Adam's Overlook is a great place to stop for a rest on your way up to the summit of Mount Greylock. From here you will be rewarded with beautiful views over Adams. This is a small parking lot with no facilities, but if you keep going up to the summit there is a lodge with facilities. It is worth

1

0

Frequently Asked Questions

What types of touring cycling routes can I find in Berkshire County?

Berkshire County offers a diverse range of touring cycling experiences, from easy, paved rail trails to more challenging on-road routes with significant elevation changes. You'll find paths winding through rolling hills, tranquil valleys, and lush forests, often alongside scenic lakes and rivers like Onota Lake and the Housatonic River.

Are there any easy or family-friendly touring cycling routes in Berkshire County?

Yes, Berkshire County is home to several easy and family-friendly options. The Ashuwillticook Rail Trail is a popular choice, offering a gentle, paved surface and scenic views of the Hoosic River Valley, suitable for all skill levels. There are 8 easy routes in total, providing accessible options for beginners and families.

Where can I find challenging touring cycling routes in the region?

For those seeking a challenge, Berkshire County features routes with significant elevation changes and more demanding terrain. For example, the The Spoke bicycle shop – Fitch Overlook loop from Harriman-and-West Airport is a difficult route with nearly 900 meters of elevation gain. In total, there are 28 difficult routes available for experienced touring cyclists.

Are there any loop routes for touring cyclists in Berkshire County?

Yes, many touring cycling routes in Berkshire County are designed as loops, allowing you to start and end in the same location. A popular example is the Ashuwillticook Rail Trail Head loop from Lanesborough, which offers a moderate 42 km loop experience of the rail trail. Another option is the Ashuwillticook Rail Trail Head loop from North Adams.

What scenic viewpoints can I expect to see along the touring cycling routes?

Berkshire County's routes often provide stunning vistas. You can enjoy breathtaking views of the Taconic Range and the Catskill Mountains. Specific highlights include the Veterans' War Memorial Tower at the summit of Mount Greylock, Stony Ledge, and Mount Everett Lookout, which offer panoramic views of the surrounding landscape.

Are there any waterfalls accessible near touring cycling routes?

Yes, Berkshire County is home to several beautiful waterfalls. While some may require a short hike from the cycling route, notable ones include Bash Bish Falls, the tallest single-drop waterfall in Massachusetts, and the waterfalls at Natural Bridge State Park. Wahconah Falls State Park also offers scenic cascades.

What is the best time of year to go touring cycling in Berkshire County?

The best time for touring cycling in Berkshire County is generally from spring through fall. The region's lush forests and rolling hills are particularly beautiful in the spring with new growth, and in the fall with vibrant foliage. Summer offers warm weather, but spring and fall provide comfortable temperatures for longer rides.

Can I combine my touring cycling trip with visits to towns or cultural sites?

Absolutely. Many cycling routes pass through or connect charming historic towns like Great Barrington, Lenox, Stockbridge, and Williamstown. These towns offer opportunities to stop at local shops, cafes, and farmer's markets. The region is also known for its cultural institutions, many of which are set amidst beautiful grounds accessible by bike.

What do other touring cyclists enjoy most about cycling in Berkshire County?

The area is highly rated by the komoot community, with an average score of 4.6 stars from over 20 reviews. Reviewers often praise the stunning natural beauty, the variety of terrain from gentle rail trails to challenging climbs, and the peaceful atmosphere of the region's valleys and forests.

Are there options for parking near the touring cycling routes?

Yes, many popular touring cycling routes, especially the rail trails, offer designated parking areas. For instance, the Ashuwillticook Rail Trail has multiple access points with parking available near towns like Lanesborough and Adams, making it convenient to start your ride.

Is it possible to access touring cycling routes using public transport?

While public transport options directly to trailheads might be limited, some towns in Berkshire County are served by regional bus services. It's advisable to check local transit schedules and routes in advance to see if they align with your chosen starting points for touring cycling.

Most popular routes in Berkshire County

Hiking in Berkshire County

Most popular attractions in Berkshire County

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

Didn’t find what you were looking for?

Check out more Cycling routes throughout Berkshire County below and find the perfect route in your destination.

HousatonicEast Mountain State ForestOctober Mountain State ForestSavoy Mountain State ForestPittsfield State ForestBates Memorial State ParkBalance Rock State ParkCampbells Falls State ParkLeeCheshireAdamsLenox DalePittsfieldLake Mansfield Recreation Area And Conservation ForestFlorida State ForestPeru State ForestSavoy Wildlife Management AreaGreat BarringtonNatural Bridge State ParkMill Brook ReservoirWilliamstownClarksburg State ParkBash Bish Falls State ParkClarksburg State ForestWahconah Falls State ParkNorth AdamsHopkins Memorial ForestLenoxEugene D. Moran Wildlife Management AreaTaconic Trail State Forest

Other places to explore

Nearby adventure guides

Things to Do in October Mountain State Forest

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