Connersville was an important site along the Whitewater Canal, and was the site of the Whitewater Valley Canal Co.'s headquarters. That building, the Canal House, was erected in 1842 and is now on the National Register of Historic Landmarks. The canal no longer runs through Connersville, and the building was used as a bank after its tenure as headquarters.
Elmhurst is a historic mansion built in 1831. It was once owned by President Lincoln's secretary of the interior, Caleb Smith. It operated as part of the Underground Railroad, a series of safehouses used by escaping slaves in the 1800s. Political figures, including Henry Clay and Benjamin Harrison, are believed to have been entertained in the home. It was modeled partly after the White House in Washington and was called the "White House of Indiana" during the 19th century. It subsequently was operated as a girls school, sanitarium and military academy.
Although it is open by appointment only, the Fayette County Historical Museum is home to many exhibits and Connersville memorabilia. Its offerings include Civil War relics, an exhibit on Connersville's industrial heritage, and other important Indiana artifacts. One peculiar memento is the 1924 Penrose trophy, awarded to the Lexington Motor Co. for placing first in the Pike's Peak Hill Climb auto race. The auto manufacturer left Lexington for Connersville, and stayed there until 1928.
The Whitewater Valley Railroad ran through Connersville and operated as a commercial transport and freight railway during the late 19th and early 20th centuries. Since 1972, the railroad has offered tours and passenger transport as a non-profit operation. Today, it is a popular local attraction, offering journeys from Connersville to neighboring Metamora, in addition to holiday-themed rides and private rentals. The Whitewater Valley Railroad considers itself to be an operating railroad museum.
Although no monuments currently mark its significance, visitors to Connersville might be interested to know it was the site of the nation's first high school band. Connersville is also the home of athlete Matt Howard, who journeyed to the NCAA Final Four with his Butler Bulldogs basketball team in both 2010 and 2011. Connersville High School also has won two Indiana boys basketball championships and is the hometown of Phil Cox, the 1972 Mr. Basketball award winner for the state.
