Pip 'Pinto' Squeak and his family moved to Ponyville when he was a foal, from their original home in Trottingham. They moved in the fall, meaning the family had moved in just in time for Ponyville's Nightmare Night celebration! After that weekend, Pip started school with Cheerilee and the town's foals.

Pipsqueak, despite his smaller size, is the same age as his larger/taller classmates. As an adult, he isn't much taller than the average foal or filly. Even with his diminutive stature, though, miniature ponies have just as much natural strength as their full-size pony relatives(and in some cases, even more). Since the majority of miniatures are Earth ponies, they are well known for being naturally hardy, and incredibly strong in proportion to their size. Pip here has gotten plenty of practice in keeping up with his taller classmates.

His small stature is due to him and his family being Shetland ponies! Like the naturally taller, horse-like inhabitants of Saddle Arabia, The ponies of Trottingham naturally differ in stature compared to most of Equestria, growing shaggier hair and tending to be born with coat patterns more often. Most Shetlands are Earth ponies, with pegasus or unicorn Shelties being a rare occurrence.

Pip earned his cutie mark (a pair of golden horseshoes, oriented to look like tracks) for his sense of exploration and leadership.

During the summers, Pipsqueak works with Scootaloo, Sweetie Belle, Apple Bloom, and a few other friends as a camp counselor at the Cutie Mark Day Camp, leading such activities as hiking, foraging, and his personal favorite, scavenger hunts!