When a well off man from the city arrives in a hick town to woo a wealthy widow, he encounters first an ornery model T ride to the shabby hotel, then his rival for the widow as they go on to a local fair. tempers flair and a challenge to a boxing match is met.
Donald's sister Dumbella sends her three sons Huey, Dewey, and Louie to visit their uncle Donald. They prove to be quite a handful for Donald, even with help from his book on child rearing.
Goofy, staying at the Sugar Bowl resort, demonstrates the basics of downhill skiing, which the titles and announcer insist is pronounced "SHEEing". The equipment is, of course, of the era. As you can imagine, Goofy has much trouble keeping his skis parallel and pointing downhill. The final ski jump conveniently lands Goofy right back in bed.
Mickey's going golfing, and Pluto is his caddy. Besides the usual caddy duties, Pluto runs to the ball and points to it. But when the ball lands in a gopher hole, Pluto's got another task: chase the gopher. They eventually chase each other through a number of holes in a knoll where Mickey is trying to putt out, causing the knoll to collapse.
Tom heads for a big city penthouse to become acquainted with a rich pretty female cat that lives there. He brings her Jerry as a gift and does some humiliating things to Jerry. Jerry, in turn, attracts the attention of another cat who also becomes interested in the female cat. It eventually turns into a fight between Tom and the other cat for the lady's hand but Jerry is the one who gets her in the end.
Tom ties up Spike and sneaks into the courtyard of the glamorous Toodles Galore with his bass, hoping to woo her with his song, much to the annoyance of a sleeping Jerry.