The Society's emblem depicts an Indian and Pilgrim in profile, based on the mid 17th century settlement date of Southold (c. 1640). The depiction of the Indian is, however, inaccurate for the period as the style of head dress is not that of an early colonial Algonquin which would have been present on Long Island; but is original to the great plains tribes such as the Sioux.
Traditionally, Algonquin men and women wore their hair arranged in two long braids while decorating their faces and arms with brightly colored paint. In some cases, men (primarily warriors and dancers) also wore "roach headdresses," which were often made of stiff animal hair, especially porcupine guard hair, moose hair, or deer's tail hair. However, by the early 1800s some Algonquin chiefs did begin to wear large, feathered headdresses like their neighbors in the western United States.
The mistake regarding the headdress was first made by the artist Henry Prellwitz (1865-1940), who designed the predecessor of the Society's design for the 1915 celebration of the 275th anniversary of the founding of Southold Town. It was used extensively in materials for the celebration, including being struck as a gold medal. The seal he designed for that celebration was later edited by his son, Edwin Prellwitz (1896-1976), to use as the emblem of the Southold Historical Society in 1960. (See bottom right.)
This design remained in place until a few years ago when it was again modified and updated to look as it does today. The decision was made at that time to keep the original idea behind the design as first envisioned by Henry Prellwitz, even though the Indian headdress is, indeed, incorrect for our period of Settlement.