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This collection contains letters that Woodburn Shrewsbury wrote about friendship among soldiers, courtship and marriage, and Presbyterian ministers visiting Madison, Indiana, in 1864 and 1865. Shrewsbury wrote his first letter from Madison House Hospital in Montgomery, Alabama, during his service in the 4th Kentucky Mounted Infantry Regiment.

During and just after the Civil War, Woodburn Shrewsbury wrote 3 letters (14 pages) to his friends Charles, with whom he had served in the 4th Kentucky Mounted Infantry Regiment, Company H (January 8, 1864), and Will (September 27, 1865, and October 19, 1865). Shrewsbury wrote to Charles about his experiences at Madison House Hospital in Montgomery, Alabama, and discussed his beliefs about the strength of friendships formed during military service. He also reported on the flooding of the Alabama River. In each of his letters, Shrewsbury commented on women, courtship, and marriage. Upon hearing of Will's desire to marry, Shrewsbury cautioned him against marrying before the age of 30. He also told Will of his future plans, including the possibility of purchasing oil lands in Kentucky, and shared his opinion of a group of Presbyterian ministers who had just visited Madison, Indiana, where he lived with his parents.