No one seems to recall who designed the Town of Windham's official seal. Research indicates that its first appearance on the cover or insert of the Annual Town Reports was for the year ending December 31, 1956, however there doesn't appear to be a description of its origin within the report.

While the artist may be the subject of some debate, the topics depicted are somewhat easier to decipher. In the center, we find one of our original inhabitants, a Pawtucket, leisurely navigating Cobbetts Pond. His destination (or perhaps departure point, given the slant of the canoe), being Indian Rock to the right. Some argue that the gray shape was originally drawn as a shelter of some sort, or was meant to depict Butterfield Rock, however, given the "hollowed out" area and overall theme of the seal, Indian Rock seems the more likely choice.

In the background, stately evergreens encompass the Pond offering but a glimpse of the landmark Searles Castle looming in the distance.