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Routes
Road cycling routes
United States
Vermont
Bennington County

Readsboro

The best road cycling routes around Readsboro

19

riders

4

rides

Road cycling routes around Readsboro are situated within the Green Mountains, offering a mountainous terrain with varied elevations. The region is characterized by lush forests and the presence of the Deerfield River, which carves through the landscape. Vermont Route 100, known for its scenic qualities, also passes through the area, providing a framework for many cycling paths. This setting provides cyclists with a mix of challenging climbs and scenic descents.

Best road cycling routes around Readsboro

  • The most popular road…

Last updated: April 30, 2026

4

riders

#1.

View of the Deerfield River – Hoosac Tunnel East Portal loop from Whitingham

50.8km

02:28

700m

700m

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

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Moderate

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

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

Hard

4

riders

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

Moderate

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

Moderate

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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.

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Named after Fort Pelham from the French and Indian War, the lake provides a pleasant view as you ride, along with a beach area for cooling off if you decide to take a break. Additionally, there are miles of trails surrounding the lake to explore if you choose to combine your ride with some hiking.

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This 40 acre woodland was donated to the Franklin Land Trust by Alastair Maitland in 1992. This cool stretch of road takes you along the forest offering shaded roads in the summer time and amazing foliage colors in the fall. The forest is popular with bird-watchers, so keep your eyes peeled as you ride through here, you never know what you might see.

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Historic covered bridges such as this one are traditional in the area, and it is great to see them maintained. The Bissel Covered Bridge was built in 1881. By the mid-20th century the bridge was due to be replaced by a modern steel and concrete structure. The local town opposed the new structure, and the original bridge was rebuilt and kept to the original specifications. The bridge still features a wooden structure and wooden floor.

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Mill Brook Reservoir is a small lake surrounded by trees. If you pull off the main road by the old covered bridge there is a viewing platform where you can see the waterfall from Mill Brook as it fills the reservoir.

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The Hoosac Tunnel is a working 4.75-mile (7.64 km) active freight railroad tunnel in western Massachusetts. The East Portal of the tunnel can be found in the town of Florida. It is on the big bend of the Deerfield River and not far from the roadside, so it is easy to go and visit.

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The Hoosac Tunnel is a working 4.75-mile (7.64 km) active freight railroad tunnel in western Massachusetts. The East Portal of the tunnel can be found in the town of Florida. It is on the big bend of the Deerfield River and not far from the roadside, so it is easy to go and visit.

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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.

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Frequently Asked Questions

What kind of terrain can I expect on road cycling routes in Readsboro?

Road cycling routes around Readsboro are primarily situated within the Green Mountains, offering a mountainous terrain with varied elevations. You can expect a mix of challenging climbs and scenic descents, with lush forests and the Deerfield River carving through the landscape. Vermont Route 100, known for its scenic qualities, also passes through the area, providing a framework for many cycling paths.

How many road cycling routes are available around Readsboro?

There are 4 road cycling routes detailed in this guide for the Readsboro area, offering a range of experiences from moderate to difficult.

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

Readsboro, nestled in the Green Mountains, offers beautiful cycling conditions during the warmer months. Spring brings fresh greenery, while summer provides lush landscapes. Autumn is particularly scenic with vibrant fall foliage, though cooler temperatures and potential for leaf litter on roads should be considered. Always check local weather conditions before heading out.

Are there routes suitable for beginners or those looking for an easier ride?

While the region is characterized by mountainous terrain, there are moderate options available. For example, the View of the Deerfield River – Hoosac Tunnel East Portal loop from Whitingham is a moderate 31.6-mile route, and the Waterfall – Porter Hill loop from Whitingham is a moderate 20.5-mile trail, both offering varied landscapes without the most extreme climbs.

Are there challenging routes for experienced road cyclists?

Yes, Readsboro's mountainous terrain provides excellent challenges for advanced riders. The Hoosac Tunnel East Portal – Jarvis Hill loop from Whitingham is a difficult 42.9-mile path with significant elevation gain. Another challenging option is the Hoosic River – Hoosac Tunnel East Portal loop from Beaver Island, which covers 80.8 miles with over 1200 meters of ascent.

What natural features can I expect to see while road cycling around Readsboro?

You'll be surrounded by the lush Green Mountains, offering breathtaking natural beauty. The Deerfield River flows through Readsboro, providing scenic views, and routes may offer glimpses or access to the nearby Harriman Reservoir. The region is rich in natural areas, including the Readsboro Town Forest, perfect for appreciating local flora and fauna.

Are there any routes that feature waterfalls?

Yes, the Waterfall – Porter Hill loop from Whitingham is a moderate 20.5-mile trail that leads through varied landscapes and includes a waterfall as a notable feature.

What are some of the longest road cycling routes in the area?

For a longer ride, consider the Hoosic River – Hoosac Tunnel East Portal loop from Beaver Island, which spans 80.8 miles. Another substantial option is the Hoosac Tunnel East Portal – Jarvis Hill loop from Whitingham, covering 42.9 miles.

Are the road cycling routes typically loop trails?

Yes, all the road cycling routes featured in this guide are designed as loops, allowing you to start and finish at the same point without needing to retrace your path.

What makes road cycling in Readsboro unique compared to other regions?

Readsboro offers a unique road cycling experience due to its location within the scenic Green Mountains, providing a backdrop of challenging and picturesque routes. The presence of the Deerfield River, the quiet rural setting with less traffic, and access to scenic roads like Vermont Route 100 contribute to an engaging and beautiful cycling adventure.

Is there specific information about parking for road cycling routes in Readsboro?

While specific parking locations for each route are not detailed in this guide, Readsboro's rural nature often means roadside parking or designated public parking areas in the town center or near trailheads may be available. It's advisable to check local regulations or community information for specific parking guidance before your ride.

Can I expect scenic views along the road cycling routes?

Absolutely. The routes in Readsboro are known for their scenic beauty, traversing the Green Mountains and often offering views of the Deerfield River. Vermont Route 100, which passes through the area, is particularly recognized for its picturesque qualities, ensuring a visually rewarding cycling experience.

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