Briarcliff-Peekskill Trailway

Parking is available at the following road crossings:

Spring Valley Road [41.208014N  73.835422W];

Teatown Lake Reservation (use the Lakeside or Cliffdale-Teatown trails)

John E. Hand Park [41.220597N  73.835926W];

Croton Dam - south end [41.225109N  73.854215W];

Croton Dam - north end [41.228145N  73.860308W];

Colobaugh Pond Road [41.243045N  73.879261W];

Watch Hill Road [41.254911N  73.897429W];

Sportsman’s Center (gated at times) [41.257073N  73.900724W];

Blue Mountain Reservation (seasonal fee) [41.270035N  73.921681W].

Briarcliff Peekskill Trailway connects Briarcliff Manor to Peekskill. Along the way, it wends through forest and wetland, under power lines, and past backyards. 

The Briarcliff Peekskill Trailway is always close to private property so hikers are encouraged to stay on the trail at all times.Even as it goes through deep woods, the trail borders homes when it crosses paved roads. Because the trailway is a linear footpath, hikers must retrace their steps, leave a car where they will end their hike, or rely on public transportation. Circuit hikes are possible because the trailway either connects to or is near five parks,  

The Briarcliff Peekskill Trailway is on a route that was purchased in 1929 as part of a plan to connect Briarcliff Manor with Peekskill. Only the section of the proposed parkway between Briarcliff and the Armory on Route 9A in Ossining was ever built. The rest of the route became a footpath officially designated a trailway in 1977.