The first settler in the area of Painted Post that the settlers first called Tuscarora (and a few years later, Middletown) was Samuel Brown Rice who arrived in this part of the lower Canisteo River Valley early in 1791. He built the first house erected by a non-Indian in this part of the valley, a short way up Tuscarora Creek from where it joins the Canisteo River. He was soon joined by a number of his neighbors from Chemung Town in the next county, Montgomery, where he and they were all living at the time of the first national census in 1790.
It was first named "Tuscarora" and then renamed "Middletown" when Steuben County was set off from Ontario County in 1797. The first settler was Samuel Rice who came to Tuscarora from Connecticut by way of New Hampshire and then Chenango County in New York with a stop in Chemung Town in Montgomery County. He was the husband of Lucretia Martin (who was the sister of Martha Martin, the wife of Henry Tracy who has been named as a son of Jonathan Tracy (all of them among the first generation of settlers). The first white child born in the town, on 5 April 1791, was Samuel and Lucretia's son, Stephen. Others of that first generation of settlers were Reuben and Lemuel Searles, Oliver Miller, George Goodhue, John, James and Isaac Martin, Jonathan Tracy, Abel White, James Benham, Asahel Stiles, Silas Morey, Elisha Gilbert, William Wombaugh, and Martin Young. The Rice and Martin families were both from Cheshire, New Haven County, in Connecticut... the Tracys were from Preston, New London County in Connecticut. As would be expected, the names of these first settlers and members of their families appear many times in the early town records as holders of various civic offices. Middletown (its name was again changed, in 1808, to "Addison" in honor of a British author popular at the time, Joseph Addison) grew up around the point where Tuscarora Creek joins the Canisteo River, and is situated on both sides of the streams in the southeast section of the county. Here the river valley is about three miles wide but narrows on either side of the town to about one mile wide. The township includes much hilly upland (some hills rising to three or four hundred feet) broken by valleys of tributaries of the Canisteo, the principal one of which is Tuscarora Creek.