Cheshire Rail Trail loop from Brattleboro

If you're looking for a challenging touring cycling adventure that bridges two states, the Cheshire Rail Trail loop from Brattleboro delivers. This difficult 42.2-mile (67.9 km) route, with 2519 feet (768 metres) of elevation gain, will take you approximately 4 hours and 36 minutes to complete. It's best suited for experienced cyclists with a robust bike, ready to tackle varied terrain and explore the scenic connections between Vermont and New Hampshire.

What to expect on Cheshire Rail Trail loop from Brattleboro

This touring cycling route isn't a simple loop but a journey connecting Brattleboro, Vermont, to the historic Cheshire Rail Trail in New Hampshire, primarily via the Ashuelot Rail Trail. You'll navigate a mix of gravel, crushed stone, cinder, and packed earth, with some sections, particularly around downtown Keene, offering smoother pavement. Expect picturesque New Hampshire scenery, from wooded landscapes and natural rock walls to glimpses of Mount Monadnock and water features like Rockwood Pond. While the trail generally follows a level railroad grade, the varied surface conditions, including potentially rough areas, large rocks, or soft sand, mean you'll need to stay alert. The northern sections, especially between Walpole and Keene, are notably more challenging, making a mountain bike, gravel bike, or hybrid with wider, knobby tires essential.

Planning your visit

To access the Cheshire Rail Trail from Brattleboro, you'll typically connect to the Ashuelot Rail Trail near Hinsdale, New Hampshire, which is just across the Connecticut River. Given the trail's varied surface and potential for rough spots, especially after rain, a sturdy bike is non-negotiable. While the trail is multi-use and popular year-round, fall foliage offers a particularly scenic ride. Always check local conditions, as some sections can be muddy or have tall grass, and be aware of open manholes on the Stone Arch Bridge in Keene.

Trail details

• Distance: 42.2 miles (67.9 km)
• Elevation gain: 2519 feet (768 metres)
• Difficulty: difficult
• Estimated time: 4 hours and 36 minutes