In 1884, Webb married Leila Howard Griswold, and they had two sons: Henry Walter Webb, Jr. (c.1885–1919) and State Senator J. Griswold Webb (1890–1934).
In 1912, he went with a fellow student by car from New York City to Vancouver, a then unprecedented adventure.
Philip Webb | Nick Webb | Jack Webb | Webb County, Texas | Webb County | Webb School (Bell Buckle, Tennessee) | Robert Webb | Del Webb | Morgan Webb | John Webb | Jim Webb | Jimmy Webb | James Webb Space Telescope | Freddie Webb | Beatrice Webb | Alexander S. Webb | That Mitchell and Webb Look | Samuel Griswold Goodrich | Rufus Wilmot Griswold | Dan K. Webb | Chick Webb | William Webb Ellis | Webb Wilder | Webb School | Webb Institute | That Mitchell and Webb Sound | Shirley Webb | Philip Carteret Webb | Nick Webb (musician) | Marc Webb |