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Paralleling the Connecticut and Massachusetts borders, which lie only a few miles away, the Harlem Valley Rail Trail is a beautiful paved wooded pathway along the former New York & Harlem Railroad corridor that is accessible to users of many types and abilities.
Trail advocates ultimately envision a 46-mile trail from Wassaic in Dutchess County to Chatham in Columbia County. The trail is over halfway complete, following the closing of the 8-mile gap between Millerton and Under Mountain Road in 2020. For now, trail users can ride uninterrrupted from Wassaic to Taconic State Park.
Overall, the trail is bucolic and easygoing throughout. The asphalt pavement is well maintained and mostly flat. Scenery is generally wooded, though the path passes through a variety of landscapes, including wetlands, creeks, some open grasslands, tree farms, and farmland. The trail features numerous parking lots and access points, mileposts, signage, and benches.
The 10.7-mile southern section begins at Wassaic Station, the northern terminus of the Metro-North Railroad Harlem Line, a commuter route. Because the Metro-North line ends here, the trail parallels the active rail line only a short distance. The northern endpoint of this trail section is Millerton, which offers a quaint downtown with restaurants, shops, and a historical one-room schoolhouse near the trail parking lot.
Thirteen miles later, you'll find yourself on Orphan Farm Road in the hamlet of Copake Falls. There is a short (0.4-mile) portion where the trail—after passing another small parking lot—goes along an unpaved road before resuming. As it approaches Taconic State Park, it passes over the scenic Bash Bish Brook (Bash Bish Falls are about a mile east, over the Massachusetts border) before arriving at the entrance to the state park, which includes some public amenities. As the trail continues, the tree canopy opens up to reveal the Orphan Farm Meadow, flanked by mountains—including the Catskills—on two sides.
After a gap of 0.7 mile, the northern section of trail picks up at Black Grocery Road and continues north to Anthony Street in a residential area of Hillsdale. Currently this segment is only 1.5 miles long and is difficult to access. However, pleasant views along the way include vast fields of Christmas trees and other active farmland.
To reach the southern terminus at Wassaic Station from the intersection of NY 22 and NY 55 in Pawling, head north on NY 22, and go 6.8 miles. Keep left to remain on NY 22, and go 13.1 miles, past the hamlet of Wassaic. Following signs for the Metro-North commuter railroad, turn right into the Wassaic Station parking lot. Note that this is a paid parking lot. (Train travelers can also take the Metro-North Harlem Line from as far south as Manhattan to the last stop, Wassaic Station.)
To reach the north end of the southern segment, follow the directions above, and continue on NY 22 N another 11.2 miles to Millerton. Turn right onto US 44 E/Main St. The trail and parking lot are on the first block, within 500 feet, on your right.
To access the middle trail segment, follow the directions above to Millerton, and continue another 8.4 miles north on NY 22. Turn right onto Under Mountain Road. The trail and parking lot are 0.4 mile away, on your left.
To access the trail in Copake Falls, continue 5.9 miles north of Under Mountain Road on NY 22, and make a hard right onto Orphan Farm Road in Copake Falls. After 0.6 mile, the trail and parking lot are on your right.
To reach the trail at Black Grocery Road from NY 23/Main St. and NY 22 in Hillsdale, head south on NY 22. After 0.4 mile, make a sharp right onto Anthony St. and then an immediate left onto Underhill Road. Take Underhill 1.4 miles, then make a left onto Black Grocery Road. Go to the end of Black Grocery Road, where there is a parking area next to the trail.
To reach the northern terminus in Hillsdale from NY 23/Main St. and NY 22 in Hillsdale, head west 0.2 mile on NY 23/Main St., then turn left onto Anthony St. After 0.1 mile, at the intersection with White Hill Lane, go straight to continue on Anthony St. Ext. (do not go left to stay on Anthony St.). The trail is 100 feet up the hill on the left, in a residential area. Parking is available at a lumber store (312 White Hill Lane) by the rail-trail kiosk.
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