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Bordering Connecticut on the east, the town of Lewisboro is often noted for its rich natural landscape—including horse farms, wooded fields, and seven lakes (Lake Katonah, Lake Rippowam, Oscaleta Lake, Lake Waccabuc, Truesdale Lake , Lake Kitchawan, and Timber Lake). Lewisboro also encompasses the hamlets of Cross River, Goldens Bridge (both with shopping centers), South Salem, and Waccabuc.

Since Lewisboro itself has a rural rather than commercial atmosphere, residents often go to Cross River and Goldens Bridge for shopping needs and for access to the Metro North (located in Goldens Bridge). The town borders two county parks—Mountain Lakes Park to the north and the Ward Pound Ridge Reservation—making for plenty of space to go hiking, camping, and fishing.