The show starts off with Stan and Molly entering the diner where they ate years ago when they first drove through Waterford Falls. They are surprised though to find that no one knows who Stan is except for Ryan who instantly begs to become Stan's cameraman. Stan also announces he and Molly have no place to stay, so Pete decides to show them some open property in the town. They find a place they really like, but it is only for rent, but they will be able to move into it that night. It costs $500 a month, and they are also surprised to find Gary Jamison, their new butler -- who comes with the house. Gary instantly lays don the groundrules with Stan that he does the chores -- not Stan. Stan then meets the head of the cheese factory, who unveils his own cheeshead .... of Stan!! When Mr. Hawkins gets angry about Stan employing Ryan, Stan finds, without his permission, that he is now housing Ryan. Stan constantly finds people coming in and out, and his house is like the whole towns, but in a
Stan decides to enter the race for town mayor when he discovers the same man has been mayor for five terms. Stan just wants to give people another choice, but he is surprised to learn of the cover up behind the mayor and the involvment that Fred Hawkins has in it, as well as the rest of the town.
When Stan decides to join Pete and Lou Peterson for a boy's night out at Jimmy's Tavern to play billiards for ""dimes"" and ""nickels,"" he's accused of using trick shots every time he sinks a ball. Meanwhile, Gary invites Molly to join him and the girls at the weekly bridge game that meets at the Hooper residence. Ryan and Chelsea consult Stan for planning their future and Chelsea contemplates her opportunities at Penny's College of Cosmetology and Tattoo U. When it's discovered that ""dimes"" and ""nickels"" are worth more—much more—Stan scrambles to save his opponent, Lou Peterson, from selling the diner.
Stan gets interested in turkey hunting, ordering every possible item in preparation for an outing, then he enlists Chelsea to prevent Molly from cooking anything for Thanksgiving dinner.
Fred's frustration mounts because Gary invites Molly and Chelsea to join the 'guys-only' Christmas caroling group, ""The Silent Knights."" Meanwhile, when the Petersen Boys run out of Stan's favorite treat, Clara Meek's apple pie, Stan sets out to secure the recipe before the ailing Clara dies.
Stan burglarizes the diner to prove Waterford Falls is not inviolable to crime.
Stan discovers his biggest fan lives nearby and enlists the help of a cranky mailman to find him.
A typo in the ""Cheese Quarterly"" magazine naming Molly as Fred's mistress brings the tabloids and press down on Stan.
The town’s snowplough operator has a thing for Stan, but when Stan denies her, the whole town suffers.
Stan decides to investigate his property upon learning the people of the town believe there are ghosts living in his boathouse.
After inadvertently getting the milkman fired, Stan helps him start his own “business”.
Stan suspects that the town’s doctor, Doc Goodman, isn’t really a doctor.
Problems arise after Stan mistakes a wolf that he found to be a cute puppy.