The Reluctant Bridegroom begins with Sky Winslow, the son of Chris and Dove Winslows, agreeing to return East and bring a wagon train of brides to the men of Oregon City. As experienced as he is on the trail, the past hurts of an unfaithful wife and the care for a twelve-year-old son who truly needs a mother's love make sky an unlikely candidate for such an assignment.

On the long trip from New York to Oregon, two of the women who join the wagon train will make their impact on Sky Winslow. Rebecka Jackson, in hope of finding a new start, is leaving a broken past. Rita Divall is a dance hall girl who knows the way to break down a man's defenses. Join them on their trail west!