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

Cheshire Recreational Rail Trail

Hard

5.0

(9162)

9,163

riders

Cheshire Recreational Rail Trail

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

A

Start point

Parking

Get Directions

1

13.4 km

Troy Train Depot

Highlight • Historical Site

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 …

Tip by

2

32.1 km

State border

Highlight • Monument

Always fun to see these. Dated 1884. On gravel road.

Tip by

B

64.1 km

End point

Parking

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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

Elevation

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

Highest point (350 m)

Lowest point (150 m)

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Weather

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Today

Thursday 7 May

16°C

5°C

0 %

Additional weather tips

Max wind speed: 19.0 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'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.

Is the Cheshire Recreational Rail Trail suitable for beginners or families?

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.

How long does it typically take to cycle the entire trail?

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.

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

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.

Are there towns or amenities accessible directly from the trail?

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.

Does the trail connect with other cycling paths?

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.

What is the best time of year to cycle the 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.

Is the Cheshire Recreational Rail Trail dog-friendly?

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.

Are there any permits or fees required to use the trail?

No, there are typically no permits or fees required to access and use the Cheshire Recreational Rail Trail.

Where can I park to access 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.

What type of bike is best suited for this trail?

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.

Nearby routes

Moderate

4

Ashuelot Recreational Rail Trail

03:47h

42.0km

130m

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