|Debut||In the Loop|
|Voiced by|| Dan Kiesler|
Fabio De Luigi
Harold Winston is a groundhog and a one day camper who first appeared in In the Loop.
Harold was dropped off at Littlest Pet Shop by his owner. He is a know-it-all who often does not get his facts right. At first, Russell did not like him very much; however, in the end, the two ended up being friends. He reveals that his facts are inaccurate because he misspeaks due to his vast knowledge. He has a habit taking a breath while sucking in his stomach simultaneously.
- "The finest bamboo is from Indiana."
- Adding an underwater elephant step is sure to improve your timing."
- Harold is modeled after Bill Murray, whose film Groundhog Day is a parody of his episode debut.