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Routes
Bike touring routes & trails
United States
New Hampshire
Cheshire County
Keene

Cheshire Recreational Rail Trail

Hard

4.8

(6060)

12,801

riders

Cheshire Recreational Rail Trail

05:00

52.4km

470m

Cycling

Cycle the challenging 32.6-mile Cheshire Recreational Rail Trail, featuring varied terrain, historic bridges, and scenic views.

Last updated: February 26, 2026

Waypoints

A

Start point

Parking

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1

21.9 km

Cheshire Rail Trail

Highlight (Segment) • Trail

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 …

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52.4 km

End point

Parking

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Way Types & Surfaces

Way Types

50.7 km

1.25 km

311 m

192 m

Surfaces

51.0 km

1.38 km

< 100 m

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Elevation

Elevation

Nothing selected – click and drag below to see the stats for a specific part of the route.

Highest point (260 m)

Lowest point (90 m)

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Weather

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Today

Friday 8 May

14°C

1°C

21 %

Additional weather tips

Max wind speed: 18.0 km/h

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This route was planned by komoot.

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Frequently Asked Questions

What is the surface and terrain like on the Cheshire Recreational Rail Trail?

The trail primarily features a varied surface of gravel and dirt, including hard-packed gravel, crushed stone, cinder, sand, and packed earth. While some segments, particularly between Walpole and Keene, are hard-packed, other areas can be rough with large rocks, flooding, or erosion. You might also encounter soft or muddy spots.

Is the Cheshire Recreational Rail Trail suitable for beginners or less experienced cyclists?

The trail's difficulty ranges from easy to advanced. The section south of Keene, extending nearly 19 miles to Fitzwilliam, is generally smoother and less challenging. However, the northern section, especially between Walpole and Keene, is more difficult due to rocks, erosion, and steep inclines. Beginners should be prepared for varied conditions and consider starting on the southern segments.

What type of bicycle is recommended for this route?

Due to the varied and sometimes challenging surfaces, a mountain bike is generally recommended. While some cyclists have managed with road bikes equipped with 25mm wheels, you should be comfortable riding on dirt and gravel if choosing this option.

What kind of scenery and landmarks can I expect along the trail?

You'll experience abundant natural beauty, including wooded landscapes, natural rock walls, and water features like wetlands and Rockwood Pond. The trail also offers views of Mount Monadnock and passes through charming towns such as Troy and Fitzwilliam. A notable landmark is the impressive Cheshire Rail Trail Stone Arch Bridge over the Ashuelot River in Keene, built in 1863.

Are there any breaks in the trail or connections to other paths?

Yes, there is a break in the trail as it passes through the town of Keene, requiring cyclists to navigate through town before rejoining the rail path. In Keene, the Cheshire Rail Trail also connects to other local trails like the Jonathan Daniels Trail, the Appel Way Trail, and the Ashuelot Recreational Rail Trail. The route also passes through sections of the Wantastiquet-Monadnock Trail and various segments of the Cheshire Recreational Rail Trail.

Where can I find parking and access points for the trail?

The trail connects towns from Fitzwilliam to Walpole, offering various access points. You can find parking in towns like Keene, Troy, and Fitzwilliam, which also provide access to amenities. Specific parking areas are typically available at trailheads within these towns.

What is the best time of year to cycle this trail?

The trail offers different experiences throughout the year. While it's a multi-use trail enjoyed in various seasons, conditions can vary. Winter sees use by snowmobilers, cross-country skiers, and snowshoers. For cycling, spring through fall generally offers the most favorable conditions, though some sections can be muddy even without recent rain.

Do I need a permit or pay an entrance fee for the Cheshire Recreational Rail Trail?

There is no mention of permits or entrance fees required to access the Cheshire Recreational Rail Trail for cycling.

Is the Cheshire Recreational Rail Trail dog-friendly?

The Cheshire Recreational Rail Trail is a multi-use trail, popular for various activities including hiking. While specific dog regulations are not detailed, multi-use trails in New Hampshire are generally dog-friendly, often requiring dogs to be on a leash. It's always a good idea to check local signage or town regulations for specific leash laws.

Are there amenities like cafes or shops along the trail?

Yes, the trail provides opportunities to stop in towns such as Keene, Troy, and Fitzwilliam. These towns offer access to amenities like coffee shops, restaurants, and museums, allowing you to combine nature immersion with community exploration.

How long does it typically take to cycle the entire Cheshire Recreational Rail Trail?

The entire 42-mile route, from Keene to Westminster, typically takes around 5 hours to complete by touring bicycle, depending on your pace and stops. The total duration for the route is approximately 18,020 seconds (about 5 hours).

Nearby routes

Moderate

4

Ashuelot Recreational Rail Trail

03:47h

42.0km

130m

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