The Legendary Founding of Smithtown

The history of the Town of Smithtown begins in 1665 with its founder, Richard Smythe (later known as Richard Smith). The story of how he acquired the land is one of Long Island’s most enduring pieces of local folklore: the Legend of the Bull.

The Bull Story: A Tale of Land and Lunch

According to local tradition, Smith acquired title to the land from a Native American chief, who offered him all the territory he could ride a bull around in a single day.

• The Longest Day: Smith famously chose the longest day of the year (the summer solstice) in 1665 to maximize his time.
• Whisper the Bull: The bull, named Whisper, was reportedly trained for riding.
• Bread and Cheese Hollow: Legend holds that Smith paused for lunch in a hollow, inspiring the name of Bread and Cheese Hollow Road (Suffolk County Road 4), which still defines a portion of the town's border with Huntington today.
• The Legacy: Though historians consider the story a myth, its power is undeniable. The town embraces the legend, and a massive five-ton bronze statue of "Whisper the Bull" stands as an iconic landmark at the intersection of Routes 25 and 25A.

The Actual Founding and the Nicolls Patent

While the bull story makes for great local color, the actual founding of Smithtown was a typical 17th-century legal battle over land grants.

• The Land Grant: The land was originally granted to Smith by Lion Gardiner (the first Lord of Gardiner's Island) in 1663. Gardiner had received the tract as a reward from the local Nissequogue Grand Sachem, Wyandanch, whose daughter he had helped rescue.
• The Formal Recognition: Richard Smith spent years fighting legal battles to secure his claim. In 1665, the English Colonial Governor Richard Nicolls formally ratified the sale by awarding Smith the Nicolls Patent, officially establishing his claim and the founding date of the town.

Industrialization and Suburban Expansion

For over 150 years, Smithtown remained a pastoral and agrarian community. This changed dramatically in the 1870s with the arrival of the Long Island Railroad.

• Railroad Boom: The railroad brought summer visitors, allowing wealthy New Yorkers to construct elaborate large estates, transforming the town into a popular leisure destination. Stops like Kings Park, Smithtown, and St. James became key commercial centers.
• Post-War Transformation: The most significant change occurred after World War II. The national expansion of suburbia reached Smithtown, leading to a population explosion. Farmlands were converted into housing developments, schools, and modern commercial centers, drastically changing the landscape and cementing Smithtown’s role as a major, established bedroom community in Suffolk County.
• Enduring Heritage: Today, the town’s rich past is actively preserved by the Smithtown Historical Society, which maintains several historic properties, including the Epenetus Smith Tavern, allowing residents to continually connect with the history of the "Bull Smiths" and the patriots who defended the area during the British occupation in the Revolutionary War.