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The 3.1-mile Kress Family Trail in Roxbury occupies the former route of the Shepaug Valley Railroad (the Shepaug, Litchfield and Northern Railroad). The railroad was famously known as the “crookedest railroad east of California,” meandering 32 miles to cover a distance of 18 miles as the crow flies. The trail charts a serpentine course through the river valley, linking the Orzech Family Preserve to the River Road, Erbacher, and Golden Harvest Preserves. The Roxbury Land Trust manages these natural areas.
The best place to start is the entrance to the Orzech Family Preserve on Botsford Hill Road, near the sky-blue barns of Orzech Farm. There is parking here, as well as a kiosk with a map and tips for encountering wildlife (bears, specifically). Past the gate, you will find yourself plunged into a fairy-tale forest, where rows of slender hemlock trees envelop the trail in a leafy embrace. Offshoot hiking paths peel off from the rail-trail, taking travelers deeper into the woods. Blue blazes mark trees along these paths for navigation.
Although you can catch glimpses of the Shepaug River between the trees, Volunteers Bridge offers the best viewpoint of the watercourse. This quirky wooden footbridge was built by—as you may have guessed—volunteers from Roxbury, and clearly takes its inspiration from truss railroad bridges of years past. It’s located 1.4 miles from the trailhead. Across the bridge is the River Road Preserve, with picnic tables, a map kiosk, and more trails. Back on the trail, the route winds through verdant woodland and bucolic meadows to finally end on Minor Bridge Road.
Though the trail is open for cycling, its uneven surface makes for a bumpy ride in places. You are welcome to bring your dog, but dogs must remain leashed.
The Roxbury Land Trust has built a small parking area at the northern end of the trail; it's located off Botsford Hill Road near Route 67. To reach the parking lot: From I-84, take Exit 9 for CT 25 toward Brookfield. Head north on Hawleyville Road/CT 25, and go 3.5 miles. Turn right onto CT 133 and continue on it 6.3 miles, then take a right onto Clapboard Road. In 1.2 miles, make a right turn onto CT 67, and in 1 mile make a final right turn onto Botsford Hill Road. The entrance to Orzech Family Preserve will be on your right.
(There is another parking area at the Minor Bridge end of the trail, but it is for Roxbury residents only with a risk of a $90 fine for those who park without a permit.)
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