Squirrel & Raccoon Baby Season: When Do Raccoons & Squirrels Have Babies. Why Is This Important? Squirrel Baby Season happens twice a year – during the latter part of the winter to the early months of the spring and from the middle part of the summer to the early portion of the fall. This is good to know when hiring a wildlife control company. Each litter … Continue reading When Is Raccoon & Squirrel Baby Season, Why Is This Important ?