[5] An abundance of natural open space, Dry-stone walls and elegant Colonial mansions are dominant features.

Apparently mistreated by British soldiers at the time of the Revolutionary War, she retreated to a solitary life in the Lewisboro area.

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.

[7] 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.

The town's unusual chevron shape is partly the result of The Oblong, created during the resolution of the boundary dispute between Connecticut and New York.

Unlike the neighboring communities of Katonah and Ridgefield, Lewisboro does not have a downtown business district.

Most residents in town do their shopping at plazas in Golden's Bridge, Cross River, Vista, or Ridgefield, CT. Lewisboro is rich in natural areas and is a component of the biotic corridor.

Lake Waccabuc is the largest and most well-known of these, and the area of town named after it has a separate post office.

Additionally, there are a number of reservoirs in the town of Lewisboro, utilized by cities such as Norwalk, Connecticut.

Housatonic Area Regional Transit (HART) operates a weekday commuter shuttle between Katonah station and the South Salem Municipal park and ride lot at 606 Old Post Rd.