Gart Williams is a contemporary New York City advertising executive who has grown exasperated with his career. His overbearing boss, Oliver Misrell, angered by the loss of a major account, lectures him about this "push-push-push" business. Unable to sleep properly at home, he drifts off for a short nap on the train during his daily commute through the November snow.
He wakes to find the train stopped and that he is now in a 19th-century railway car, deserted except for himself. The sun is bright outside, and as he looks out the window, he discovers that the train is in a town called Willoughby. He eventually learns that it is July 1888. He learns that this is a “peaceful, restful place, where a man can slow down to a walk and live his life full measure”. Being jerked awake into the real world, he asks the conductor if he has ever heard of Willoughby, but the conductor replies, “Not on this run…no Willoughby on the line.”
That night, he has another argument with his shrewish wife Jane. Selfish, cold and uncaring, she makes him see that he is only a money machine to her. He tells her about his dream and about Willoughby, only to have her ridicule him as being “born too late”, declaring it her “miserable tragic error” to have married a man “whose big dream in life is to be Huckleberry Finn”.
The next week, Williams again dozes off on the train and returns to Willoughby where everything is the same as before. As he is about to get off the train carrying his briefcase, the train begins to roll, returning him to the present. Williams promises himself to get off at Willoughby next time.
Experiencing a breakdown at work, he calls his wife, who abandons him in his time of need. On his way home, once again he falls asleep to find himself in Willoughby. This time, as the conductor warmly beckons him to the door, Williams intentionally leaves his briefcase on the train. Getting off the train, he is greeted by name by various inhabitants who welcome him while he tells them he’s glad to be there and plans to stay and join their idyllic life.
The swinging pendulum of the station clock fades into the swinging lantern of a train engineer, standing over Williams’ body. The 1960 conductor explains to the engineer that Williams “shouted something about Willoughby”, before jumping off the train and being killed instantly. Williams’ body is loaded into a hearse. The back door of the hearse closes to reveal the name of the funeral home: Willoughby & Son.