This covered bridge was named after the McCleery Family. Samuel R. McCleery was the son of William and Priscilla, and the grandson of James and Jane, all of which lived in Fairfield County. Samuel fought in the Civil War from 1861-1865 in the 11th Ohio Calvary. He lived in Pleasantville with his wife Sarah and their 2 children. He later became a merchant at the local hardware store.

Originally, this covered bridge spanned Walnut Creek on Leonard Road, near Baltimore. In 1983, it was relocated to Pleasantville Road, where it was shortened due to rotted wood. It was relocated one more time to it's present location in 2006 and restored.

Jacob Rugh Brandt was born in 1836 in Fairfield County. He learned the bridge building trade early in life from Jonathon Coulson. Coulson was a local bridge builder that often visited the Brandt Farm. In 1858, Brandt began working for the Fairfield County Commissioners. He designed and built numerous schoolhouses, churches, and small bridges throughout the county. Built in 1864, McCleery was Brandt's first covered bridge. He went on to build numerous covered bridge during his 43 year career. Brandt would cut and test fit the timbers in his front yard before shipping them to the construction site. Many people called him "Blue Jeans Brandt" because he usually wore denim head to toe. Jacob Rugh Brandt died in 1911.