The World Trade Center, seen here in February 2001, was prominently featured in the episode.
At Moe's Tavern, Moe informs Homer and his friends that one of them must be a designated driver, and Barney loses the choosing draw. After Barney drives the drunken men home in Homer's car, Homer allows him to use it to drive himself home, expecting Barney to return it the following morning. In his distressed state, Barney disappears with the car. Two months later, Barney returns to Moe's Tavern, unable to recall where he left the car. Homer later receives a letter from the New York City government, which informs him that his car has been found parked in the World Trade Center plaza and will be destroyed if not picked up in 72 hours. Homer reveals to the family that he had once been to New York before when he was 17 years old, and had a horrible experience. Marge and the children persuade Homer to go retrieve the car, and he reluctantly agrees.
When the family arrives in Manhattan, they decide to split up. Upon arrival at his car, Homer discovers it has been issued many parking tickets and has been wheel clamped. While waiting for parking officer Steve Grabowski to come and remove the clamp, Homer drinks an excessive amount of crab juice from a food vendor and needs to urinate, but is afraid to leave his car behind. After several hours of holding it in and failing to urinate in a mailbox, he finally goes to the restroom at the South Tower's indoor observation deck, but discovers that it is out of order and must use the one at the top of the North Tower. While he is doing that, the officer arrives at the car and, finding no one present, issues another ticket and leaves; Homer's subsequent "D'oh!" echoes across the city. Meanwhile, the rest of the family tours the Statue of Liberty, Little Italy, Chinatown, and the Empire State Building. Bart leaves the group to visit the offices of Mad magazine, and is in awe when he sees Alfred E. Neuman. The family attends a Broadway musical about the Betty Ford Clinic, and then takes a carriage through Central Park to where they are planning to meet Homer.
Upon returning to the car, Homer realizes he must make it to Central Park to find his family and leave before it gets dark. Ignoring the wheel clamp, he tries to accelerate and in the process destroys the car's fender. Homer stops by a road construction crew and steals a jackhammer so he can use it to remove the clamp. The car is freed from the clamp, but further damaged as a result. Homer races to Central Park and reunites with his family. While driving back to Springfield, the family reflects on their wonderful time, while Homer's hatred for New York remains.