5.0
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69
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23
rides
Gravel biking in Cheshire County, New Hampshire, features diverse landscapes characterized by rolling hills, river valleys, and extensive rail trail networks. The region offers a mix of terrain, including unpaved surfaces and routes with significant elevation gains. Riders can explore classic New England woodlands and areas around prominent features like Mount Monadnock. This varied geography provides a suitable backdrop for different gravel biking experiences.
Last updated: April 23, 2026
15
riders
Hard gravel ride. Very good fitness required. Mostly paved surfaces. Suitable for all skill levels.
5
riders
59.4km
04:29
1,210m
1,210m
Hard gravel ride. Very good fitness required. Mostly paved surfaces. Suitable for all skill levels.

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2
riders
22.8km
01:50
330m
330m
Moderate gravel ride. Good fitness required. Mostly paved surfaces. Suitable for all skill levels.
2
riders
31.4km
02:23
490m
490m
Hard gravel ride. Very good fitness required. Mostly paved surfaces. Suitable for all skill levels.
2
riders
73.2km
05:25
730m
730m
Hard gravel ride. Very good fitness required. Mostly paved surfaces. Suitable for all skill levels.
2
riders
30.8km
02:17
710m
710m
Hard gravel ride. Very good fitness required. Mostly paved surfaces. Suitable for all skill levels.
4
riders
33.4km
02:00
490m
490m
Hard gravel ride. Very good fitness required. Mostly paved surfaces. Suitable for all skill levels.
3
riders
23.1km
01:29
410m
410m
Moderate gravel ride. Good fitness required. Mostly paved surfaces. Suitable for all skill levels.
3
riders
58.8km
04:04
730m
730m
Hard gravel ride. Very good fitness required. Mostly paved surfaces. Suitable for all skill levels.
2
riders
37.9km
02:41
520m
520m
Hard gravel ride. Very good fitness required. Mostly paved surfaces. Suitable for all skill levels.
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Popular around Cheshire County
There is a small green space near bridge that is a great place to stop for a snack or lunch.
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This quiet lake and its beach are perfect for taking a rest off of the bike. With a lovely sandy beach to get into the water, the lake is perfect for a cool off on a summers day.
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Harrisville is a charming small town centered around a historic 19th-century industrial mill complex. The town is frequently photographed as an example of picturesque New England.
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Fitzwilliam is a picturesque small town in Cheshire County and is home to the 16-acre Rhododendron State Park. It offers a historic feel and wonderful views, and is also listed on the National Register of Historic Places.
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The Troy Train Depot is an old rail station from the now defunct B&M Rail line. The depot is found on the Cheshire Recreational Rail Trail. There are some informational plaques on the outside of the building providing some background on the railroad that used to run through the area.
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The Troy Train Depot is an old rail station from the now defunct B&M Rail line. The depot is found on the Cheshire Recreational Rail Trail. There are some informational plaques on the outside of the building providing some background on the railroad that used to run through the area.
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The Putney Mountain area is offering more than 800 acres of conserved land along with around 15 miles of hiking trails along the Windmill Hill Ridgeline.
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This railroad converted to cycling path is perfect for a pleasant ride along the river.
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Cheshire County offers a wide selection of gravel biking routes, with over 25 trails available for exploration. These routes cater to various preferences, from moderate rides to more challenging adventures.
Cheshire County is an excellent destination for gravel biking due to its diverse landscapes, extensive rail trail systems, and natural attractions. You'll find a mix of hills, valleys, and waterways, providing varied terrain through classic New England woodlands and river valleys.
The gravel trails in Cheshire County feature a mix of surfaces. You can expect crushed gravel, dirt, and some paved sections, especially on the rail trails. After wet weather, some sections, particularly on the Ashuelot Rail Trail, might include grass, dirt, and muddy patches, adding to the adventure.
Yes, the extensive rail trail system, such as the Cheshire Rail Trail and Ashuelot Rail Trail, generally offers easier sections suitable for families. These multi-use trails provide a more relaxed riding experience away from traffic.
Parking is available at various points along the major rail trails. For the Cheshire Rail Trail, you can find parking in Keene and ride north towards North Walpole or south towards Fitzwilliam. Many trailheads for other routes also offer designated parking areas.
Yes, many of the gravel biking routes in Cheshire County are designed as loops, allowing you to start and end at the same point. Examples include the Halifax Village Center – Green River Covered Bridge loop from Bonnyvale Environmental Education Center and the Cold River – Gustin Pond loop from Washington.
You can encounter several interesting landmarks and natural features. The Cheshire Rail Trail passes the historic Troy Train Depot. The Ashuelot Rail Trail follows the Ashuelot River and features numerous bridges, including several covered bridges just off the main path. For scenic views, consider routes near Mount Monadnock Summit or along the Connecticut River.
Yes, the Ashuelot Rail Trail is known for its scenic appeal, with numerous bridges, including several covered bridges located just off the main path. The Halifax Village Center – Green River Covered Bridge loop also includes a covered bridge as a highlight.
While specific conditions vary, spring, summer, and fall generally offer the best conditions for gravel biking in Cheshire County. The fall foliage provides particularly stunning scenery. Be mindful that some sections can become muddy after heavy rain, especially on trails like the Ashuelot Rail Trail.
Absolutely. Beyond the rail trails, Cheshire County offers challenging gravel rides with significant elevation gains. Routes like the Harrisville loop from Dublin or the Putney Mountain loop from Putney require good to very good fitness and provide a more demanding experience.
The area is highly rated by the komoot community, with an average score of 5.0 stars. Reviewers often praise the diverse terrain, the extensive rail trail networks, and the beautiful natural backdrops that make for an engaging and varied gravel biking experience.
While specific public transport options directly to trailheads might be limited, major towns like Keene, which serve as access points for trails like the Cheshire Rail Trail, may have public transport connections. It's advisable to check local transit schedules for the most up-to-date information.


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