Lewisboro has had two noteworthy historical characters. Sarah Bishop was the hermit of West Mountain. Apparently mistreated by British soldiers at the time of the Revolutionary War, she retreated to a solitary life in the Lewisboro area. A spot known as "Sarah Bishop's Cave" is on the hill on the north side of Lake Rippowam, near Mountain Lakes Camp. The second historical character appeared around the time of the Civil War. The Leatherman was a wanderer who got his name from homemade leather garments. He is frequently mentioned as being in Lewisboro in the middle of the 19th century. He followed a route past homes that would offer him a meal and reappeared at the same doorsteps for 25 years. One of the hiking destinations in Ward Pound Ridge is to the Leatherman's cave, reportedly one of his more frequent homes. In 1987 a 10k trail race called "The Leatherman's Loop" was started to honor his legacy and continues every spring at the Ward Pound Ridge Reservation.