The town of Bedford was settled in 1837. Early residents, Hezekiah and Clarissa Dunham donated the land that serves as Bedford Public Square. The Dunhams built one of the area's first homes in 1852, which stands at 729 Broadway with the letters H & D above the doorway. Early settlers were attracted to the area by the abundance of natural resources and a large waterfall for mill sites. Bedford also served as a stagecoach stop on the route from Cleveland to Pittsburgh. The road or Turnpike Road as it was called was originally part of the Mahoning Indian Trail. By 1895 the road was renamed Main Street (and later Broadway) when the Akron, Bedford, and Cleveland Railway Company (ABC) traversed the middle of the street carrying passengers. The interurban is called "America's first high speed long distance electric interurban" with speeds in excess of 60 miles per hour.
Most of Bedford's commercial block buildings were constructed between 1891 and 1929. The business district had several car dealerships as automobiles replaced horses. The Hudson-Essex dealer was at 707 Broadway and Chevrolet at 15 North Park Street. Key events in Bedford history include an 1893 fire that
destroyed the west side of Main Street. On October 21, 1920, George "Jiggs" Losteiner and his gang attempted to rob the Bedford branch of the Cleveland Trust at 686 Broadway. When Bedford citizens were alerted to the robbery, they engaged the robbers in a twenty-minute gun battle that killed one assailant and wounded several more. All were captured and the local citizens became heroes. Archibald Willard, painter of the Spirit of '76, and baseball Hall of Fame great Elmer Flick were born in Bedford. Bedford's business district was placed on the National Register of Historic Places in 2004.
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