Harlem Valley Rail to Trail to Falls

Description: Northeast Dutchess County and southeast Columbia County, NY, and a section in Litchfield County, CT -- starting from the Metro-North train station at Wassaic. 59 miles, moderate hilliness, (3900 vertical feet). Variations A + B avoid the longest hills (58 miles, 2700 vertical feet) Variation C continues on north to the village of Hillsdale, with hills (70 miles). Variation D takes it further to explore quiet roads + hills in the north end of the valley (80 miles). For a much shorter route (30 miles) which uses some of the same roads, see Harlem Valley Wandering For a much easier route in this area, see Amenia to Millerton - Rail Trail and Roads. An option of interest to riders using the Metro-North trains might be to use the "connection" at mile 58 to join the Quaker Ridge route and finish at the Metro-North train station in Pawling (total 77 miles) or even Brewster (total 92 miles).

Highlights: Endless rolling quiet roads with beautiful farms in Dutchess and Columbia counties. Climb to the biggest views from a Dutchess county road. Lunch in a quiet village. Ride sections on the nicest paved "rail trail" around. Take a side trip to visit Bash Bish Falls, the prettiest waterfall in the Berkshires. All this is accessible by train from Manhattan. One of our favorite rides.

Characteristics: Moderate hilliness. At least one section on an off-road paved "rail trail". For both the main route and the variations, traffic interaction is typical for routes on this website.

Hill climbs: Total vertical climb around 3900 feet. The longest climb is 550 vertical feet (McGhee Hill / Skunks Misery Rd). Fortunately the average grade of this climb is less than 4%, but it starts with a steep 50 foot section around 9%. There are two climbs around 150-200 feet at about 7-8% grade. Variations A+B avoid the bigger two of those hills, but keep the steep climb of about 150 vertical feet at 7-8% grade (just north of Sharon CT). Variation C adds about 900 feet to the total vertical, including a hill with about 400 vertical feet of closely linked climbing (on North Rd), with much of that at 7-10% grade. Variation D adds about 1600 feet to the total vertical, including the steep North Rd hill, and also a hill with about 230 feet of climbing mostly less than 6%. Traffic: The main route has about 3 miles of high-speed and/or high-volume motor vehicle traffic. Also about 2 miles of moderate traffic; and about 12 miles of traffic which is more than low, but often less than moderate. The rest of the road segments often have low traffic. 4.5 miles are off-road on the Harlem Valley Rail Trail.