In 1844 he took up an apprenticeship in the carpenter and building trade, and in 1850 he moved to Janesville, eventually expanding his contractor business into lumber retailing and manufacturing,[1] with extensive raw timber holdings in Wisconsin and Michigan.

[2] On May 29, 1880, he married Julia Stow of New Haven, Connecticut.

They had four children: Allen, Henry, Julia and Webster (who died as an infant).

[3] Julia Lovejoy was a well-known citizen of Janesville and lived to 103.

[5] His former home, now part of what are known as the Lovejoy and Merrill-Nowlan Houses, is listed on the National Register of Historic Places.