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Smithtown was originally known as Smithfield and was settled in the mid sixteen hundreds. Smithtown has an unusual history, which, according to Smithtown tutors has a lot to do with the capabilities of one mans bull.

Local historians have variations on one story about Richard Smith after whom Smithtown was named. The basic outline of the legend is that Richard Smith was responsible for rescuing and returning the daughter of the local tribe’s Native American Chief. The daughter had been captured on her wedding night during a raid by Narragansett Indians and then taken against her will to Connecticut. As a reward for saving the life of his daughter, the chief offered Smith a substantial tract of land the size of which was entirely dependent on how far Smith was willing to travel with the proviso that he had to encircle the area of land in just one day and while riding on a bull. Smithtown tutors tell us that Smith took the challenge, but he cleverly waited until it was he longest day of the year in order to maximize the daylight hours. The land that he managed to cover during the duration of the day roughly equates to the present day borders of Smithfield.

Smithtown tutors acknowledge that students in Smithfield are encouraged to go and visit the statue of the Smithtown Bull. They believe that it is very important the students appreciate this piece of history. The Smithtown Bull was built to remind locals of the unusual way in which this town was founded. The statue is located on the prominent corner of the village of Smithtown at the fork of the Jericho Turnpike and St. Johnland Road. The statue is said to be to scale of Richard Smith’s bull who was named Whisper. Some residents do not approve of this large bronze statue as they feel it is not aesthetically pleasing.

During Smiths time and following the establishment of Smithtown, he was frequently at odds regarding boundaries, and entered into many boundary disputes. One of the longest running was between Smithtown and Huntingdon over the correct boundary, an argument that in the end he won. The road that separates Smithtown and Huntington has an unusual name; it is called Bread and Cheese Hollow Road. The name is derived from nearby Bread and Cheese Hollow, which is where legend has it, Smith stopped on the longest day of the year when encircling his land in order to have some lunch which consisted of bread and cheese. Smith became a very wealthy man due to this negotiation and he was able to buy more land and construct properties.