Polk County was formed in 1835 from land that was originally in Greene County. When the county was formed it was much larger in square miles than it is today. The original boundaries were about 32 miles by 54 miles. It took in almost all of Cedar and Dallas Counties and some of Dade, St. Clair and Hickory Counties. When the county was formed, the Govenor of the State appointed the county officials including the sheriff who also served as the county collector. The first sheriff did not have a jail and it was two years later in 1837 when the county court ordered that one be built. They authorized $800.00 to build a three story stone building. After six months and no bids were made, they ordered the commissioner of buildings to design a wooden frame building. They allowed an extra $400.00. In 1840, the first jail was completed. Just one block east and one block south of the current square in Bolivar, it was two stories with a rock foundation with triple walls. One layer was oak timber 12X12's, laid horizontally then 6X8 oak placed vertically and the inner was inch and a half oak planking. Someone set this first jail on fire a few years later and it burned.
The second jail was built one block south of the southwest corner of the square. The jail was two stories with double brick walls and oak timber inner linings. This jail was completed in 1857 and was sturdy built. The inner walls were made of oak and twenty-penny nails were driven every square inch. The only access to the second floor cells was an outside staircase.
In 1879, the County Court decided this jail was inadequate and contracted to have it torn down and a new jail built that would provide living quarters for either the sheriff or a deputy on the lower floor. They hoped this would help in stopping any escape attempts and eliminate the need for such heavy reinforced walls, ceilings, and floors. By January 1880, this jail was completed and a deputy for Sheriff Henderson Boone was chosen to live on the lower floor. According to records, crime must have been happening at a low rate because as of February 5, 1880, no one had been put in the new jail yet so that it could be dedicated. The third jail served as the home of the sheriff and lockup for prisoners for 23 sheriffs in a 98-year time span. Glen Carson was the last sheriff to live in the jail. In 1976, when Charles Simmons was elected, some people were hired to live at the jail and night dispatch but Sheriff Simmons never took up residence there. This jail was also deemed outdated and the current jail was built in 1978.
This current building housed the sheriff's office along with the jail. It was built just to the east in the same block as the third jail. The third jail then served as a meeting place and museum until 1993 when, due to deterioration of the mortar and the need for additional space, it was torn down. In 1991, a building was purchased just across the street, west of the main building, and was converted into office space, a briefing room, interview room, and large evidence room. In 1994, the need for more storage space was evident, so another piece of land was purchased just across the street, east of the main building, on which was constructed a 40'X80' storage building and vehicle impound garage. In 1995, the existing jail was expanded from its original 16-bed capacity to a 33-bed capacity with additional office space. In April of 2002, the offices of the sheriff were moved across Main Street to the Law Enforcement Building (LEB). The bed capacity was increased to 39. In 2005, a kitchen was added to allow for meals to prepared in the jail and not contracted out.