John Rowlett Woodside was born at Rowlett’s Landing, Franklin County, Kentucky, in 1814.  The descendant of a Revolutionary soldier, Woodside probably inherited and certainly developed the fortitude necessary to survive and thrive on the Kentucky frontier.  A sense of adventure led him westward into the howling wilderness of Missouri in late 1830’s.  Woodside’s formal education began as a young adult attending subscription schools in Scott County, Missouri, while he earned a living in hard physical labor chopping wood.  A quick learner, Woodside began teaching school in 1838, and a keen sense of duty led him to political office and election as Scott County Assessor in 1840.  During this period Woodside married Miss Emily H. Old, the union resulting in eight children.

     Woodside furthered himself by learning the surveying trade, and soon after moving to Oregon County, Missouri, was employed by the federal government to help survey the south central Missouri region.  Woodside found and settled land at Thomasville, then the county seat of Oregon.  In 1845 the county seat was moved to Alton, Missouri, and John surveyed the site of the town.  In the same time period he surveyed and named the town of West Plains, Missouri, naming it for, “the plains west of Thomasville”.  The 1845 record book of the first session of the Oregon County Circuit Court reflects his elected position as County Clerk.  

     In the late 1840’s, J.R. Woodside began reading law and passed the Missouri Bar.  Woodside supervised the building of a new county courthouse when the county seat was moved from Thomasville to Alton.  He was a member of the state convention in Jefferson City, March, 1848.  Woodside was serving in the Missouri Legislature in the House of Representatives as war clouds gathered over the nation and state. 

     Woodside initially argued against secession; however, when word came to Jefferson City of the invasion of Missouri by Union troops, Woodside quickly left to return and warn his citizens of Oregon County.  Abandoning all he possessed there, Woodside took only a fast horse and made one of the quickest trips on record via horseback to his home county.

      Woodside’s acquaintance with Circuit Judge James McBride (now Brigadier General McBride) led to his immediate appointment as a Colonel in the 7^th Division of the Missouri State Guard with authority to raise a regiment.  Woodside did much to recruit and raise Oregon and Howell County troops for the MSG, with an objective of defending Missouri from foreign troops.  Among those recruits was John’s son, J. Posey Woodside, who was elected Captain. 

Both men led troops into battle under General McBride at the Battle of Oak Hills or Wilson’s Creek in August 1861.  Both men were critically wounded in subsequent fights while in MSG and Confederate service. (After disbanding of the Missouri State Guard both men enlisted in the 4th Missouri Infantry.  In an hour-long pitched battle at Mammoth Spring in March, 1862, Woodside was seriously wounded, and reported killed by Union authorities.   Both John R. and Posey Woodside were captured on more than one occasion.  John R. Woodside was captured three times and escaped once.  He eventually was imprisoned in Gratiot Street Prison, St. Louis. 

     Following the war John R. returned to Oregon County, and when allowed by repeal of the Drake Constitution, ran on the Democratic ticket for Circuit Judge of the newly formed Thirteenth District, part of Judge James McBride’s old circuit.  He easily defeated an old adversary, Unionist William Monks, and served as an outspoken advocate of Confederate causes the remainder of his life.  John R. and J. Posey Woodside were instrumental in the forming of a United Confederate Veterans Camp in West Plains.  He continued to serve as Circuit Judge for another fourteen years.  He was a master mason and member of the Southern Methodist Church for 35 years.  Old age and infirmities finally required Judge Woodside to step down, and about a year later, in 1887, John R. Woodside died at his home in Thomasville overlooking the Eleven Point River with a book in his hand. 

By Lou Wehmer.  Sources:  “John R. Woodside, A Man of His Time”, Ann Woodside, published West Plains Gazette, Issue #17, May-June 1982, pages 48-51, all portions quoted with permission of Russ Cochran, Editor and Publisher.

Official Records, Series 1, Volume VIII, pages 336-339.

A Reminiscent History of The Ozark Region, Goodspeed Brothers, Chicago, Illinois, 1894, pages 786-787.

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