The first jail in Lebanon was erected, circa 1799-1803 on the public square in Lebanon.  The small cedar log cabin Fiddlers Grove Jailconsisted of two stories; the upper level for the Sheriff and the lower level for the jail cells.  Samuel Roseborough was elected the first sheriff of Wilson County in 1799-1803. Other jails were built at different locations around the town square.

Fiddlers Grove Jail is equipped with one of the iron jail cells from an early jail near the town square. Wilson County jail workhouse inmates, under the direction of Sheriff Terry Ashe constructed the jail building with recycled lumber and donated it to Fiddlers Grove in 1993.