The title of the series comes from the old Irish saying, spoken by Joe Callaghan about what his brother-in-law, Jack Bailey, used to say: "May the road always rise to meet your feet, and may the wind always be at your back."
Booth Savege (Jack Bailey) and Tyrone Savege (Fat Bailey) are father and son in real life, as well as on the show.
The series was canceled after the fifth season, which did not have a clear ending to the storylines. The movie "A Wind at my Back Christmas," was made to tie up some of the loose ends.
The character Honey Bailey was played by two different actresses: Cynthia Bellevue (seasons 1-3) and Laura Bruneau (seasons 4-5). The character was said to have traveled to a sanatorium to receive treatment tuberculosis to explain the characters absence during the recasting transition.
The character Violet Bailey was played by at least two different actresses, including Victoria Collyer when she was a toddler and Natasha LaForce. Natasha is the real life sister of the baby who portrayed Zach Bailey, her characters brother.