Cheshire Recreational Rail Trail
Cheshire Recreational Rail Trail
5.0
(9162)
9,163
riders
05:59
64.1km
430m
Cycling
Cycle the challenging 39.8-mile Cheshire Recreational Rail Trail, gaining 1420 feet through varied New Hampshire landscapes.
Last updated: February 26, 2026
Waypoints
Start point
Parking
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13.4 km
Highlight • Historical Site
Tip by
32.1 km
Highlight • Monument
Tip by
64.1 km
End point
Parking
Way Types & Surfaces
Way Types
57.8 km
6.06 km
159 m
< 100 m
Surfaces
60.5 km
1.95 km
1.28 km
366 m
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Elevation
Highest point (350 m)
Lowest point (150 m)
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Weather
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Thursday 7 May
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Additional weather tips
Max wind speed: 19.0 km/h
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This route was planned by komoot.
The trail's surface is mainly gravel and dirt, with sections of packed earth, sand, and cinder. You might encounter rougher areas, mud, or loose, deep sand. While most of the trail is generally level due to its rail trail origins, there are gradual inclines. Some paved segments exist, especially within Keene.
Yes, the trail is generally considered family-friendly and easy to moderate. The southern portion, from Keene to Fitzwilliam, is smoother and less demanding, making it ideal for hybrid bikes and those seeking an easier ride. However, sections north of Keene can be more challenging with larger rocks and potential erosion.
The full 42-mile (one-way) trail can take around 6 hours to cycle, depending on your pace and stops. The komoot tour for the entire length suggests a duration of approximately 6 hours.
You'll experience picturesque New Hampshire scenery, including wooded landscapes, natural rock walls, wetlands, and views of Rockwood Pond. Keep an eye out for glimpses of Mount Monadnock. Notable landmarks include the historic Troy Train Depot, a beautiful stone arch bridge over the Ashuelot River in Keene, and a narrow gap in the hillside with steep rock walls.
Yes, the trail passes through several charming towns like Fitzwilliam, Troy, Keene, Westmoreland, and Walpole. Keene offers access to coffee shops and restaurants. In Troy and Fitzwilliam, you can see old railroad depots, with the one in Troy refurbished into a museum.
Yes, in Keene, the Cheshire Rail Trail serves as a hub, connecting with other trails such as the Ashuelot Recreational Rail Trail, the Jonathan Daniels Trail, and the Appel Way Trail. The route itself also utilizes sections of the Wantastiquet-Monadnock Trail and the Monadnock Recreational Rail Trail.
The trail offers scenic beauty throughout the warmer months. Spring and fall are particularly pleasant, with autumn providing vibrant foliage. Be prepared for varying conditions, as some sections can be muddy after rain or have loose sand, especially in drier periods.
Yes, rail trails in New Hampshire are generally dog-friendly. Always ensure your dog is on a leash and that you clean up after them to maintain a pleasant experience for all users.
No, there are typically no permits or fees required to access and use the Cheshire Recreational Rail Trail.
Access points and parking are available in the towns the trail passes through, including Fitzwilliam, Troy, Keene, Westmoreland, and Walpole. Specific parking areas are usually designated near trailheads in these towns.
Given the predominantly gravel and dirt surface, with sections of packed earth, sand, and cinder, a mountain bike or hybrid bike is recommended. A road bike would likely struggle in many sections due to the varied and sometimes rough terrain.