Tilman Bobbitt, brother of Oregon, left Monroe County and went west in 1866, and did not write or return to West Virginia until 1892. In 1892 Tilman Bobbitt was living with his daughter Eliza (Bobbitt) Anderson in Chicago, Illinois. During 1892 Tilman returned to Monroe and Greenbrier counties for a visit with the relatives he had left behind in 1866. Living at the time of his visit were two or three grandchildren, born to his daughter Susan who had married Alexander Knight. Only his brothers, Oregon and James Hill Bobbitt were living at the time of the visit. His sisters, Mary Frances (Bobbitt) Withrow, and Permelia (Bobbitt) Toothman, were the only sisters living at the time. Tilman took sick in Monroe County and died there. His body was taken back to Chicago Illinois for burial in Forest Home Cemetery.
On July 26, 1975, at the Bobbitt family reunion, held each year in Cowen, West Virginia, descendants of Oregon Bobbitt, Michael Ray Bobbitt, Ray Harvey Robbitt, Sally Bobbitt Light, Evelyn Snedegar, and Gordon Bobbitt, met the descendants of Tilman Bobbitt The descendants of Tilman were, Susie Bobbitt McGregor, Mary Ellen McGregor, Frank Bobbitt, and Billie Bobbitt Dalrymple.
In 1937, Kitty Ann (Bobbitt) Wallace, descendant of Oregon Bobbitt, through his son, Napoleon, wrote to Susan Perry, descendant of Tilman Bobbitt, through his daughter, Eliza, in which she said:
"My father, Napoleon Bobbitt and my brother Herbert Bobbitt, and I, went to visit Tilman Bobbitt, after my mother died. My mother's name was Virginia Dearing and her folks were from Wolf Creek, West Virginia. My father, Napoleon Bobbitt died in September 1920 and was buried in Logan, Iowa. My father was a mighty fine and honest man. Mr. Wallace and I have two nice sons, William Dearing Wallace, and Harold Glenrody Wallace. Both are studying dentistry in Friend, Nebraska. It is too bad we do not have a record of the various ones in our family."
When Tilman Bobbitt left Monroe County in 1866, he took with him, George and James Bobbitt, the sons of Oregon and Lucy Ann Bobbitt. They traveled in a group with horses and wagons. The men worked as blacksmiths along the way, and did day work on the farms that needed laborers. They stopped for several months in Springfield, Illinois. They lived for a short time in Pike County, Missouri, By May of 1870, George son of Oregon was living in North Platte, Nebraska. The others were living in either Nebraska or Iowa. In 1880 all were in Nebraska.