The volume provides a narrative accounting of the origins and exploits of a group of English women friends who decided to call themselves the Order of the Little Bears during World War II. Maud Isabella Milgate was the primary author of the narrative, and Dorothy Eccleston Back (or "Pat") drew many illustrations throughout the volume. Other friends in the group included Maud Milgate's sister Blanche Adelaide Milgate ("Bibs"), as well as Rose Anne James, Margaret Hessie Vince ("Meg"), and Elsie May Smith ("Smut"). Rose James wrote four pages in the volume in green ink regarding the housewarming party the Order threw for her after cleaning up her bombed-out home.

The group decided to call themselves the Little Bears in part because of one member's interest in the "Three Bears" fairy tale. They used the "Teddy Bear's Picnic" as their theme song (the lyrics are pasted in near the front of the volume). The narrative includes details about parties the group threw each other and other "binges" they held, attending church services--one member was confirmed in December 1942--acquiring a garden allotment, surviving teaching and WAAF (Women's Auxiliary Air Force) postings, and contending with a bombed-out home. In December 1942 the group put together a variety show at their local church hall; the volume includes a handwritten program for the evening as well as a poster folded and pasted into the back of the volume.

The friends' activities were primarily located in Ramsgate, Kent. Rose James was teaching in Stafford, and "Smut" left Ramsgate for her WAAF training elsewhere in England. There are several watercolor, ink, and pencil sketches throughout the volume, many of them taking up an entire page. A handful of pages at the back of the volume were not used, and several other unused pages at the back of the volume were cut out. A single loose sheet proposing creating associates of the Order, 13 months after it was created, is located at MS P761.