Pilot Grove took its name from an extensive grove of hickory trees around a watering place that guided travelers across the featureless prairie. Two trails met here, one from the Missouri River to the southwest called Georgetown Road and another heading northwest to Independence while skirting the Chouteau Land Grant. The first recorded settlement was one mile south at Mt. Vernon Branch around 1820, where the Cumberland Presbyterians established a Brush Arbor Church and Cemetery, followed by a school, mill, Methodist church, and Harris store. John McCutcheon became the first postmaster in 1833. Residents along Georgetown Road witnessed Gen. Lyon's Union march from Boonville to its defeat at Springfield in 1861, Bloody Bill Anderson's raid in October 1863, the arrival of the MKT railroad in 1873, a visit from the Orphan Train in the 1920s, and a munitions train wreck on May 6, 1945. As commercial development shifted north to the railhead, Pilot Grove was platted and formally chartered in 1873 on the farmland of Samuel Roe, who served as postmaster from 1855 to 1872. The Catholic, Baptist, Methodist, and former Presbyterian and Christian congregations of the town date from that period, as do the old city hall and calaboose. Its business district included banks, shops, and two newspapers, the Pilot Grove Bee and a German weekly, and the present recreational park later became the site of a CCC camp built in 1939 during the Depression years.