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.
Last updated: April 30, 2026
4
riders
Moderate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride.
4
riders
69.0km
03:20
960m
960m
Hard road ride. Very good fitness required. Mostly well-paved surfaces and easy to ride.

Sign up for free
5
riders
80.8km
04:09
1,260m
1,260m
Hard road ride. Very good fitness required. Mostly well-paved surfaces and easy to ride.
4
riders
60.5km
02:50
750m
750m
Moderate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride.
2
riders
33.0km
01:47
610m
610m
Moderate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride.
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
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
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.
1
0
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.
0
0
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.
0
0
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.
0
0
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.
0
0
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.
1
0
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
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.
There are 4 road cycling routes detailed in this guide for the Readsboro area, offering a range of experiences from moderate to difficult.
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.
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.
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.
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.
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.
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.
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.
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.
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.
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.


Browse the best Road cycling routes in other regions.