Herman Lodge No. 108 F.&A.M. was chartered on January 16, 1889, in DeFuniak Springs and originally met in a structure in the area of Freeport known as Tucker Town. After the lodge building burned on June 19, 1901, it was replaced with a structure near the banks of Four Mile Creek that was built of native lumber. In 1903, the building was disassembled and re-erected at its current location at the intersection of Madison Street and North Street, and it has remained in continuous use as a Masonic lodge ever since. It is an excellent example of early 1900s vernacular commercial and public architecture using a false parapet facade. The lower floor was rented to the J.J. McCaskill Mercantile Company from 1908 to 1916 for use as The People's Cash Store. In 1925, the Order of the Eastern Star was granted use of the building. In 1950, the Boy Scouts, 4-H Club, the Home Woodsmen of the World, and the Ladies' Auxiliary of the Woodsmen also rented the lodge for meetings. At the heart of the historic center of the original City of Freeport, it remains one of the few intact and active historic structures and a landmark beloved by the people of Freeport.