Harlem Valley Rail Trail provides a scenic ride through rolling farm fields and dense woods on the bed of the New York and Harlem Railroad that ran from New York City to Chatham. The rail-trail is being built in segments, and there is still work to be done to open all 46 miles of the planned trail. For now, you can enjoy three disconnected segments, which total 16 miles.
The southern end of the trail begins at the Metro North Railroad Station in Wassaic. It is possible, during non-rush hours and on weekends, to board a Metro North train in Grand Central Station and in a little more than two hours be peddling or walking along this rail-trail. As the paved trail winds north for nearly 11 miles to Millerton, it passes through a pastoral scene. Farmland stretches before and around you, followed by red-cedar scrubland and beaver ponds. In Amenia, the trailhead parking lot is on the site of the former Barton House, a large hotel that was frequented by business people and vacationers traveling from New York City.
Several railroad stations on this line have been restored: Sharon Station is now a private residence located off the trail in the town of North East. Millerton's three stations have been restored and today house local businesses. North of Coleman Station the trail crosses six reconstructed railroad bridges.
The railroad builders tamed the area's rolling terrain, and created a level corridor, by blasting through rock and building the rail bed up from the land adjacent to the corridor for a "pyramiding" effect. In several stretches, north of Route 61, the trail's higher elevation on steep embankments—in some places dropping 50 feet—provides spectacular views of the surrounding farmland. Indian Mountain, straddling the border of New York and Connecticut, is to the east. Traveling through a series of deep rock cuts, you will feel the temperature drop several degrees from the surrounding landscape.
Millerton is the current end of the first section of rail-trail. In Millerton, two restored train stations that appear to have changed little since their original construction in 1851 and 1912 flank the trail. A third station, once used for freight, stands nearby. All house local businesses today. The village offers ample opportunities for refreshment and shopping.
The next 8 miles of the railroad corridor between Main Street in Millerton and Under Mountain Road in Ancram are not open for public use.
Reaching the next open trail section requires a detour on a two-lane road. Head west on Main Street in Millerton and then north on New York State Route 22 for about 7.7 miles. Turn right on Under Mountain Road and look for the trailhead on the left. The 4-mile paved section of trail between Under Mountain Road and Taconic State Park is more wooded where the trail hugs the base of the South Taconic Mountains.
About 2.9 miles north of Under Mountain Road, the trail detours onto a scenic dirt road for 0.4 mile to bypass a privately held parcel of rail bed. The dirt road rejoins the paved rail-trail for another 0.5 mile to the entrance to Taconic State Park at Copake Falls. Scenic Bash Bish Falls is located about 1 mile east of the trailhead, just over the Massachusetts state border. Follow the hiking trail to reach the falls.
The newest completed and open section of the trail lies further north in Hillsdale, stretching from Black Grocery Road to Anthony Road. The segment is 1.5 miles and has a crushed stone surface, well-suited for mountain biking, hiking, and cross-country skiing. There are plans to pave this portion in 2014.
To reach the Wassaic trailhead: From I-84 or I-684, take State Route 22 north at Brewster. Continue north on Route 22 to the Wassaic Station of the Metro North Railroad. The station is on the right side of the road.
To reach the Taconic State Park Trailhead: From I-84 or I-684, take State Route 22 north to Brewster. Continue north on Route 22 to State Route 344, about 6 miles north of Millerton. Turn right and proceed about 0.5 mile to the triangular green. Bear to the left to the stop sign. Proceed straight about 0.3 mile to the entrance of Taconic State Park; ask the attendant where to park.