Pippi's first Christmas on land proves to be a special one. Thunder Karlson and Bloom have nowhere to go for Christmas and even their attempts to get arrested are bungled. Pippi comes to their aid and helps them to understand the true meaning of Christmas.

Pippi suddenly realizes that she is eventually going to grow up. This is not a prospect she likes and as she thinks about her future, we see her fears realized as we flash forward to a bleak future as a grown-up.

Pippi discovers that she is missing out on certain holidays because she doesn't go to school, so there is nothing to take a holiday from. She joins Annika and Tommy and attends the local school, much to the amusement of the other students and the dismay of the teacher.

Pippi and her friends join Captain Longstocking on a journey to a remote Northern Community to deliver supplies. It is a trip full of adventure as they team up with the natives to battle storms, icebergs and ""poachers.""

The field trip up North continues and Pippi and her ""crew"" must outsmart Poachers to save the rare green whales from extinction.

Pippi's friends are entering their report on the field trip up North in a competition for one of the special school prizes. Pippi decides this is worth returning to school for, and is there to disrupt the special occasion, much to the disturbance of Mrs. Prysellious and the very ""proper"" guest of honor, Mr. Rosenbloom.

An encounter with a local farmer who treats his horse very badly convinces Pippi that she has to give his animals a vacation - at Villa Villekulla. Horse and Mr. Nilsson are not too enthused with the new boarders, but the animal owner learns his lesson.

A mysterious woman arrives in the village just as a ghost is sighted at the old castle. Pippi teams up with Kling and Klang to solve the mystery of the ghost ... or is it the White Lady?

The whole town is in an uproar at the discovery of a giant footprint in the snow, presumed to be that of a mythological creature. At the prospect of the town's and townsfolk notoriety, several people are caught in the drama and crazy antics of being the first to sight and capture the creature, thereby bringing fame and fortune to themselves. All the while, Mr. Nilsson gets around undetected wearing giant snowshoes on his feet.

Bloom gets wind that he is being considered as Aunt Matilda's heir to her fortune upon her death. TK and Bloom are determined to ingratiate themselves to the crotchety old aunt, and Pippi has the task of finding charitable activities for the reformed crooks.

Pippi befriends an inept, but good-natured carpenter and manages to help him find work in the village. When his poor workmanship puts the town at risk, Pippi must step in to do some hasty renovations.

Kling and Klang have been assigned to escort two tough criminals on a train ride to a new maximum security jail. Also aboard for the ride are Tommy and Annika under Mrs. P's supervision, and to the delight of TK and Bloom, a gold shipment is loaded along with an armed guard prompting TK & Bloom's decision to get on board as well. Pippi, Horse and Mr. Nilsson decide to join the party and the antics follow as TK and Bloom assume the criminals have a plan to get the gold, and want a part of it.