Smithtown, A History: The Homes of Caleb Smith State Park Preserve

Most visitors to are familiar with the park’s main house, but not with the other structures on the property. While now used as private residences, the houses still add to the preserve’s historic feel.

According to park manager Clarence Ware, individual farms once surrounded the Smith property. In the 1880s, the Brooklyn Gun Club bought land by the Head of the River and continued to buy property to the west. Ware said these purchases combined the separate farms into the large area seen today.

On the south side of the park by Webster Pond is the Vail House. According to “Colonel Rockwell’s Scrap-Book” published by the Smithtown Historical Society in 1968, the home was built by a schoolmaster named Moses Brush who left the country soon after building the shingled house.

The name of the house comes from Aaron S. Vail, the structure’s most popular resident, who lived there in the 1800s. According to the scrap-book, Vail kept “a house of entertainment for trout fisherman.”

United States senator Daniel Webster and friends were frequent visitors to the Vail House during trout season, and Ware said that Webster Pond was named after the politician.

On the north side of the park and west of the parking lot, visitors will find the Chipman Farmhouse. According to “Colonel Rockwell’s Scrap-Book”, the house was built around 1736 when a James Chipman rented 55 acres from Daniel Smith II, Caleb Smith’s father.

The Chipman Farmhouse was used as the miller’s home after a mill was built on Willow Pond. According to the scrap-book, the mill was built around 1795 and in the early 1900s the farmhouse was sold by Captain Lewis W. David, the last miller who lived there, to the gun club.

As for the Willow Pond Mill, today only the foundation is left. The structure collapsed under heavy snow in the 1990s, according to Ware.

Walking north from the , visitors to the park will come across another structure hidden behind a number of trees. This is the Whitman House, and the home was once the residence of Eliphalet Whitman. According to the scrap-book, Whitman ran a large tannery and shoe factory in the early 1800s, and the family members were distant relatives of poet Walt Whitman.

Along with the mill and tannery, a blacksmith shop existed in the 1800s creating a small settlement around the Caleb Smith homestead. Combined with the over 500 acres of wooded lands of Caleb Smith State Park Preserve, the remaining structures stand as a reminder of the early days of Smithtown.

The preserve is open to the public Tuesday through Sunday from 8:00 a.m. to 4:00 p.m. Parking is free until Memorial Day weekend.