Cheshire Reservoir – Ashuwillticook Rail Trail Head loop from Western District HQ

The Cheshire Reservoir – Ashuwillticook Rail Trail Head loop from Western District HQ is one of those road cycling routes that offers a surprisingly easy ride for its length, covering 28.8 miles (46.3 km) with just 522 feet (159 metres) of elevation gain, all completed in about 1 hour and 51 minutes. This easy road cycling route is perfect if you're looking for a longer, scenic ride without demanding climbs, making it a great option for a relaxed but substantial outing.

What to expect on Cheshire Reservoir – Ashuwillticook Rail Trail Head loop from Western District HQ

This route combines the famously flat Ashuwillticook Rail Trail with connecting roads, offering a diverse ride. You'll glide along a smooth, paved path that winds through the Hoosac River Valley, providing extensive views of the Cheshire Reservoir and Berkshire Pond, often framed by Mount Greylock and the Hoosac Mountains. Keep an eye out for wildlife in the wetlands and forested areas, from various bird species to turtles. While the overall route is rated easy, its length provides a good workout, making it ideal for road cyclists who appreciate consistent, well-maintained surfaces and picturesque New England scenery.

Planning your visit

The loop starts from the Massachusetts Department of Conservation and Recreation's (DCR) Western Regional Office, located at 740 South Street, Pittsfield, MA. The Ashuwillticook Rail Trail itself has various trailheads with amenities like ample parking, seasonal restrooms, and picnic areas, so you'll find facilities along the way. The trail is universally accessible and well-maintained, making it enjoyable throughout the cycling season, especially vibrant during autumn foliage.

Trail details

• Distance: 28.8 miles (46.3 km)
• Elevation gain: 522 feet (159 metres)
• Difficulty: easy
• Estimated time: 1 hours and 51 minutes