Wagons East! (1994)

In the 1860s Wild West, a group of misfit settlers, including ex-doctor Phil Taylor, prostitute Belle, and gay bookseller Julian Rogers, decide they cannot live in their current situation in the west, so they hire a grizzled alcoholic wagon master by the name of James Harlow to take them on a journey back to their hometowns in the East. Comedic exploits ensue as the drunken wagon master lets his horse choose the correct fork in the road, leads them to a dried-out watering hole, and eventually guides them into Sioux territory where they are captured. The Chief, however, is sympathetic to the idea of 'white men heading back east', and offers an escort off Sioux land. Meanwhile, they must also contend with (inept) hired gunslingers who have been sent by railroad magnates to stop the journey, as they fear the bad publicity it could create for the settlers about to commence a 'land rush' into the west. Harlow's secret, that he had been wagon master for the infamous Donner Party, eventually comes out, and the group confront Harlow about his past; he chooses to walk away from the group, and they proceed on their own. The cavalry leader back at camp ends up confessing that he knew Harlow, and had taken supplies from the Donner party in order to support his troops attacking Mexico. Harlow resumes his drinking at the closest tavern, he overhears that the cavalry will be confronting the group the following day, and intends to wipe them out, as directed by the head of the railroad company. As the cavalry arrives the next day and the group "square their wagons", Harlow rides to the rescue and 'calls out' the cavalry leader to single combat. After a drawn out and comical fight scene, Harlow is victorious, and the group celebrates. Harlow and Belle decide to pursue a relationship, Julian departs for somewhere "even further west" (San Francisco), and the group rides toward the now visible St. Louis to finish the journey.