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Freedom was settled in 1794 by the Revolutionary War veteran Stephen Smith. The plantation was named Smithton in honor of the first homesteader but was then changed to Beaver Hill and finally Freedom when the town became incorporated during the last war with Great Britain in 1813.
Like many towns in Waldo County, Freedom once had many sawmills and gristmills. The town's early residents were proud of their town, its businesses, and, in particular, its wooden sidewalks. The wooden sidewalks have long since been removed, but some of the old mills and buildings in town are still standing as proof of the town's commitment to preserve the past.
An old dam at the site of one mill in town continues to hold back Sandy Pond, which contains perch, pickerel, and bass. In South Freedom many residents can point to the spot where Smith built the town's first framed house and sawmill and even give directions to Smith's grave site, which was restored a few years ago.*
One of Freedom's greatest achievements was the locally constructed Freedom Academy which served generations of students from 1836 until 1957 when fire destroyed it for the second time. In the early to mid eighties Freedom was also the home of Strawberry Fields School, a counterculture revival of the old one-room schoolhouse.