5.0
(2)
35
riders
11
rides
Touring cycling around Brattleboro offers a diverse landscape characterized by river valleys, rolling hills, and extensive forests. The region is situated along the Connecticut River and West River, providing routes with varied terrain. Cyclists can find paths ranging from relatively flat, scenic rides along riverbanks to more challenging climbs through the surrounding countryside. This area provides options for different skill levels, encompassing both paved roads and unpaved trails.
Last updated: May 1, 2026
7
riders
24.9km
01:40
200m
200m
Moderate bike ride. Good fitness required. Mostly paved surfaces. Suitable for all skill levels.
4
riders
Moderate bike ride. Good fitness required. Mostly paved surfaces. Suitable for all skill levels.

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5
riders
Hard bike ride. Very good fitness required. Mostly paved surfaces. Suitable for all skill levels.
4
riders
24.7km
02:03
340m
340m
Moderate bike ride. Good fitness required. Mostly paved surfaces. Suitable for all skill levels.
5.0
(1)
3
riders
68.1km
04:37
770m
770m
Hard bike ride. Very good fitness required. Mostly paved surfaces. Suitable for all skill levels.
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There is a small green space near bridge that is a great place to stop for a snack or lunch.
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The trail is a pleasant, peaceful hike through the woods along a number of waterfalls.
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The Native Americans of the region used to call the West River "Wantastiquet" which means "waters of the lonely way”. The Wantastiquet Trail is connected to both the mountains and the West River. This path was an important link that connected Fort Drumner and the Green Mountains.
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The Cheshire Rail Trail is a 42-mile long multiuse trail. The path is made of packed gravel and crushed rock, so it is best suited for a bike with thicker tires. The path is fully off-road, so it is a perfect option for a relaxed ride.
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The trailhead has a small gravel lot, but the trail is not heavily trafficked so you are very likely to find parking space.
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The trail is a pleasant, peaceful hike through the woods along a number of waterfalls.
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The West River flows south along the path to Brattleboro, where it merges with the Connecticut River at the Vermont - New Hampshire border. The trail here is a nice scenic bike path with views of the river and Black Mountain to the north.
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Here you can hike up the trail to Black Mountain, which is a beautiful forested trail with a number of water features. Hiking along the West River Trail for the mile south of here you get nice views of the mountain.
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While the guide lists no routes specifically rated 'easy', Brattleboro offers a mix of terrain. You can find relatively flat, scenic rides along the Connecticut and West Rivers. For example, the Black Mountain Trailhead – West River loop from Brattleboro is a moderate 15.5-mile route that follows the West River, offering a good option for those building experience.
Yes, Brattleboro has options suitable for families, particularly along the river valleys. The West River Trail, a former rail trail, offers a nearly level surface ideal for cyclists of all ages. Additionally, some mountain biking trails at Retreat Farm are suitable for beginners and families, which can be adapted for touring cycling depending on equipment.
Yes, many touring cycling routes in Brattleboro are designed as loops. For instance, the Canoe Brook Nature Preserve loop from Beatrice Aiken Preserve is a 15.3-mile route that takes you through a nature preserve. Another option is the Cannon Hill – Round Hill loop from Brattleboro, a more challenging 42.5-mile route.
Brattleboro's routes offer diverse scenery. You can find panoramic views from places like View of Vermont from Wantastiquet Mountain Stone Post, which overlooks the Connecticut River Valley. The Halifax Village Center – Green River Covered Bridge loop from Bonnyvale Environmental Education Center specifically passes by historic covered bridges, a quintessential Vermont attraction. You might also encounter natural areas like the Black Mountain area.
The best time for touring cycling in Brattleboro is typically from spring through fall. Spring offers lush greenery, while autumn is particularly spectacular with vibrant foliage, especially in areas like Hogback Mountain. Summer provides warm weather, but be prepared for potential humidity. Winter cycling is possible but requires specialized gear and awareness of snow and ice conditions.
Many routes originate from accessible points in and around Brattleboro. For example, the Black Mountain Trailhead – West River loop starts near the Black Mountain Trailhead. Other routes may start from village centers or designated parking areas near natural preserves, offering convenient access to the trail network.
Touring cycling routes in Brattleboro vary significantly in distance and duration. You can find shorter routes around 15 miles, such as the Canoe Brook Nature Preserve loop, which takes about 2 hours. Longer, more challenging routes, like the Cheshire Rail Trail loop from Brattleboro, can be over 42 miles and take several hours to complete.
Yes, cycling through Brattleboro's forests, river valleys, and natural preserves often provides opportunities to observe local wildlife. You might spot various bird species, deer, and other small mammals, especially during quieter times of day or on less-trafficked routes. Always maintain a respectful distance and do not disturb animals.
Many routes pass through or near Brattleboro's vibrant downtown area, which offers numerous amenities including cafes, restaurants, and shops. Longer routes that venture into the countryside may pass through smaller villages like Halifax, where you might find local stores or eateries. It's always a good idea to check route details and plan stops in advance.
The touring cycling routes around Brattleboro are highly rated by the komoot community, with an average score of 5.0 stars. Cyclists often praise the diverse landscape, which includes scenic riverbanks, rolling hills, and dense forests, providing varied terrain for different skill levels. The region is appreciated for its blend of natural beauty and charming village stops.
Yes, Brattleboro is an excellent hub for gravel and bikepacking. The region features a mix of well-maintained dirt roads and some woodsy doubletrack, offering a different kind of touring experience. The 'Roundabout Brattleboro' is a popular multi-day gravel tour that showcases the area's unpaved routes and challenging ascents.
Absolutely! Vermont is renowned for its covered bridges, and Brattleboro's touring cycling routes offer opportunities to see them. The Halifax Village Center – Green River Covered Bridge loop is a prime example of a route that specifically includes historic covered bridges, such as the Creamery Covered Bridge, adding a unique charm to your ride.


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