"Captain" Phillip Paddleford, a Revolutionary soldier, settled in 1790, and built Monroe's first sawmill and gristmill on what is now called Smith Brook. Peter Paddleford (1785-1859) was the inventor of the wooden Paddleford Truss for covered bridges. Many of his original bridges still stand. He was the builder of the "third Lyman Bridge" from Monroe to McIndoes, Vermont, in 1833, after the 1826 floods had taken out all bridges on the Connecticut River. It was a covered bridge of pine, over long, and stood for over 96 years, making it one of the oldest on the river.