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Routes
Gravel rides
United States
New Hampshire

Cheshire County

The best gravel rides in Cheshire County

5.0

(1)

69

riders

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.

Best gravel bike trails in Cheshire County

  • The most popular gravel bike trail is Halifax Village…

Last updated: April 23, 2026

15

riders

#1.

Halifax Village Center – Green River Covered Bridge loop from Bonnyvale Environmental Education Center

59.0km

04:14

1,310m

1,310m

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

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Hard

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

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

Moderate

2

riders

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

Hard

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

Hard

2

riders

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

Hard

4

riders

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

Hard

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

Moderate

3

riders

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

Hard

2

riders

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

Hard
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Popular around Cheshire County

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Hiking Collection by

Jamie S.

Tips from the Community

alsaman
August 26, 2025, Green River Covered Bridge

There is a small green space near bridge that is a great place to stop for a snack or lunch.

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Alex
February 15, 2024, Lake beach

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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AaronLavanchy
January 12, 2024, Harrisville

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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AaronLavanchy
January 12, 2024, Fitzwilliam

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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mtm05005
October 17, 2023, Troy Train Depot

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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mtm05005
October 16, 2023, Troy Train Depot

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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Frequently Asked Questions

How many gravel bike trails are available in Cheshire County?

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.

What makes Cheshire County a good destination for gravel biking?

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.

What types of surfaces can I expect on the gravel trails in Cheshire County?

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.

Are there any family-friendly gravel biking routes in Cheshire County?

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.

Where can I find parking for gravel bike trails in Cheshire County?

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.

Are there any circular gravel bike routes in Cheshire County?

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.

What are some notable landmarks or attractions I might see along the gravel trails?

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.

Are there any routes that feature covered bridges?

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.

What is the best time of year for gravel biking in Cheshire County?

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.

Are there any challenging gravel routes for experienced riders?

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.

What do other gravel bikers enjoy most about gravel biking in Cheshire County?

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.

Can I access gravel trails using public transport?

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.

Most popular routes in Cheshire County

Hiking in Cheshire County

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