His first significant work published was "Betsey and I Are Out", a humorous verse about a divorce that was first printed in the Toledo Blade, and reprinted by Harper's Weekly.

Carleton wrote this poem at the age of 25, when he worked as editor of the Detroit Weekly Tribune.

[3] In 1872 he published "Over the Hill to the Poor House", exploring the plight of the aged and those with indifferent families.

[citation needed] On June 24, 2007, it was reported that "the neglected burial plot of the family of rural Michigan poet, Will Carleton, whose 1872 work, Over the Hill to the Poor House, thrust him into national prominence, is getting a makeover".

[10] "What Robert Burns did for the Scottish cotter and the Reverend William Barnes has done for the English farmer, Will Carleton has done for the American—touched with the glamour of poetry the simple and monotonous events of daily life, and shown that all circumstances of life, however trivial they may appear, possess those alternations of the comic and pathetic, the good and bad, the joyful and sorrowful, which go to make up the days and nights, the summers and winters, of this perplexing world".