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Formerly comprising two separate segments—one running northward from Keene to Walpole, and the other running southward from Keene to Fitzwilliam—the Cheshire Rail Trail now runs a continuous 32.9 miles through connections made in 2017 between the two sections and the former 1-mile Industrial Heritage Trail in Keene.
Initially settled in the 1730s, Keene developed a reputation as a manufacturing center in the mid-1800s when it served as a meeting point for three railroads: the Manchester & Keene Railroad, the Ashuelot Railroad, and the Cheshire Railroad. After the decline of the railroads in the 20th century, both the Ashuelot Railroad and Cheshire Railroad were transformed into rail-trails. Today, Keene is sustained by the tourism, insurance, and education industries.
The Cheshire Rail Trail now plays host to a variety of uses, including mountain biking and horseback riding, and in winter, cross-country skiing and snowshoeing are permitted. Note that the entire route may also be used by snowmobilers, who help maintain the trail.
The trail begins in the north at State Route 12 between Alyson’s Lane and Blackjack Crossing in Walpole. Most of the northern segment between Walpole and Keene is surfaced with hard-packed gravel. Cyclists should use a mountain bike; however, a small stretch between SR 9 and the center of Keene is paved and can accommodate wheelchairs.
Those who persevere along this part of the trail will be rewarded with abundant scenery, including wooded landscapes and natural rock walls; however, trail use is sparse until you reach Keene, and there is little to draw users off the trail. Note also the challenging terrain prior to Keene, including large rocks, flooding, and erosion; turns in the trail that can be challenging to spot; and several steep inclines. After crossing SR 9, a short paved segment takes you into Keene, host to Keene State College and Antioch University.
The town is also the meeting point for three other trails, including the 0.9-mile Jonathan Daniels Trail, located one block north along Island Street; the 1.3-mile Appel Way Trail, which meets up with the Jonathan Daniels Trail and begins just east of Keene High School; and the Ashuelot Recreational Rail Trail, which connects to the Cheshire Rail Trail at Emerald and Ralston Streets and stretches 21.5 miles southwest to Hinsdale.
Heading south, the Cheshire Trail’s second segment offers a much smoother and less-challenging experience for trail users than the northern segment as it travels just under 19 miles to Fitzwilliam. This segment feels more removed from town, and the mostly gravel surface is suitable for hybrid bikes.
Passing the Marlboro Street trailhead in Keene (there is a small parking area there), you’ll head up a short, steep dirt hill and cross a quaint stone arch bridge before crossing the Ashuelot River. In about 9 miles you’ll reach Troy, where you’ll find a few restaurants, some railroad relics, and an old train depot that has been refurbished into a museum.
Continuing southeast, you’ll pass through the town of Fitzwilliam, where an old railroad depot is undergoing renovation. The route then becomes relatively remote, officially ending in the outskirts of Fitzwilliam at the New Hampshire–-Massachusetts border. Note that the most convenient southern terminus for bikers and hikers is at the trailhead at State Line Circle and SR 12, as the section of trail east of SR 12 is prone to flooding in the rainy season.
To reach the northern endpoint in Walpole from I-91, take Exit 5 toward US 5/Walpole NH/Westminster. Head east on Westminster St., and go 0.8 mile. Turn right onto US 5 heading south, go 0.7 mile, and then turn left onto VT State Route 123 E (entering New Hampshire). Go 0.3 mile, and then continue onto SR 123 E. After 0.1 mile, turn right onto SR 12 S, go 4.2 miles, and turn left onto Blackjack Crossing. The parking area will be directly ahead in 0.1 mile. The trail endpoint is 0.3 mile north along the trail.
To reach the Troy trailhead from the intersection of SR 101 and US 202 in Peterborough, follow Grove St./US 202 W/Jaffrey Road, and go 6 miles. Turn right onto Main St./SR 124, and go 6.4 miles. Turn left onto Troy Road, which becomes Monadnock St. Go 2.6 miles, and turn right onto SR 12 N. Immediately turn left onto Water St. The parking lot will be to your left after about 450 feet. The southern endpoint is located about 10.9 miles south along the trail; note that there is no dedicated parking available for trail users.
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