Calvin Ruff and Libby Lightburn(start date: 1885)
Calvin Ruff, who was white, was the son of J. Q. Ruff, a wealthy man in Galveston, TX. Libby Lightburn was an 18-year old mulatto who had moved from Texas to Louisville, KY.
In 1885, Ruff arrived in Louisville to ask Lightburn to be his wife. Interracial marriage was illegal in Kentucky, so the couple was married in New Albany, IN, where interracial marriage was also illegal, but since both of them were unknown in New Albany, Ruff was able to purchase the marriage license as a Colored man.
The state of Indiana had an 1840 law that made all white-black marriages null and void, and for those who married after the law was passed, the charge was a felony with the penalty of 10-20 years in the state prison.
For more see "Marriage of Black and White," The New York Freeman, 6/27/1885, issue 32, Col. F; and T. P. Monahan, "Marriage across racial lines in Indiana," Journal of Marriage and the Family, vol. 35, issue 4 (Nov., 1973), pp. 632-630.