Smithtown was first settled around 1665 when Richard Smith acquired the land after rescuing a Native American chief's daughter. According to local legend, Smith was granted title to all the land he could ride around on a bull in one day. The current town boundaries approximate what Smith was able to circle. There is a large statue of Smith's bull, known as Whisper, at an intersection in town. The border between Smithtown and Huntington is partially defined by Bread and Cheese Hollow Road, named after where Smith stopped on his ride to have bread and cheese.