Cheshire Rail Trail | Keene

The Cheshire Rail Trail in southwestern New Hampshire is a scenic, multi-use pathway that threads through the rural landscapes of Cheshire County, connecting towns, forests, rivers, and small villages along the route of a former railroad corridor. Stretching approximately 36 miles from Keene to Winchester, this trail is a favorite for walking, jogging, cycling, cross-country skiing, and snowmobiling, offering a versatile and accessible escape into the region’s natural and historical scenery.

Historical Background

The trail follows the path of the former Boston & Maine Railroad’s Cheshire Branch, which played a crucial role in transporting goods and passengers across southwestern New Hampshire in the 19th and early 20th centuries. The railroad corridor was gradually abandoned in the late 20th century, and local municipalities, alongside conservation groups, transformed it into a public trail in stages starting in the 1990s. By repurposing the old rail bed, the Cheshire Rail Trail preserves both history and recreational opportunities, keeping the corridor accessible for modern users while echoing the rhythms of steam engines and freight cars that once ran here.

Route and Landscape

Beginning in Keene, the trail winds westward, passing through towns like Swanzey, Troy, Fitzwilliam, and Winchester, often paralleling rivers and streams. The landscape shifts continuously: open meadows dotted with farmhouses, dense woodlands where sunlight filters through maples and oaks, and rocky outcrops offering occasional vistas of rolling hills in the distance. The flat, crushed-stone surface of the former railroad bed makes the trail accessible to families, casual walkers, and cyclists, while the gentle grades preserve the feeling of an easy, continuous journey through the countryside.

Flora, Fauna, and Natural Features

The trail’s surroundings are rich in wildlife and seasonal beauty. Spring brings wildflowers along the edges, including trilliums and violets, while summer fills the canopy with deep green foliage and the hum of insects. In autumn, the trail becomes a ribbon of fiery color, with sugar maples, oaks, and birches creating an immersive display of New England foliage. Birds such as herons, hawks, and warblers are frequently spotted, and small mammals like foxes and white-tailed deer sometimes peek through the brush along quieter stretches.

Historical and Cultural Points

Along the Cheshire Rail Trail, users encounter subtle reminders of the corridor’s railroad past: stone abutments of old bridges, occasional rails embedded in the path, and mile markers preserved from the original line. In some towns, restored depots or interpretive signs highlight local rail history, offering glimpses into how these railroads connected rural New Hampshire to broader markets and cities. Small villages along the route often have quaint cafés, general stores, or parks, providing natural stopping points for trail-goers.

Seasonal Activities and Recreation

The Cheshire Rail Trail is a year-round resource. In warmer months, it sees walkers, joggers, cyclists, and dog owners enjoying the scenic route. In winter, the compacted surface allows for snowshoeing and cross-country skiing, and some sections are open to snowmobiles, creating a multi-season recreational corridor. The trail is largely flat with occasional gentle inclines, making it suitable for beginners and families, while its length and variety of scenery appeal to more experienced cyclists or long-distance walkers seeking a day-long excursion.

Visitor Experience

Traveling the Cheshire Rail Trail feels like a slow, continuous journey through southwestern New Hampshire’s heart. Unlike crowded urban paths, it offers a quiet rhythm: the crunch of stone underfoot, the rustle of leaves in the wind, and the occasional sound of a river flowing alongside. Each town along the way invites a brief pause - perhaps for a snack, a photo, or a quick chat with locals - before continuing on the gentle path westward.

The Cheshire Rail Trail is more than just a recreational path; it is a living corridor of history, nature, and community. Walking or cycling its full length provides a layered experience: the sense of old railroads carrying goods and people, the intimate beauty of New England’s changing seasons, and the quiet pleasure of uninterrupted outdoor exploration.