Bennett was known as Kiowa Crossing until a nasty train wreck happened in 1878. A heavy rainstorm washed out a railroad bridge just east of town in May that year. A Kansas Pacific Railway train of 25 cars loaded with scrap iron ran off the missing bridge with George Platt, Frank Seldon and John Bacon on board. While the locomotive was never officially found, the rest of the train was recovered. In 1989, Lloyd Glasier (archivist with the Union Pacific Railroad) discovered paperwork indicating that the railroad had secretly found the locomotive and dug it up. They then changed all the insignia on the locomotive and put it back in service while collecting the insurance money in a complicated scam. As the dead engineers Seldon and Bacon were married to sisters whose maiden name was Bennett, Kiowa Crossing was renamed in their honor.

Bennett also has the distinction of having recorded the highest temperature ever in Colorado: 118°F back on July 11, 1888.