The Town of Dryden was first settled in 1797 and was established in 1803. It contains two villages, Dryden Village and Freeville. Part of Dryden was cut off for the village of Caroline in 1856. Caroline had been formed from the Town of Spencer in 1811. Several hamlets such as Bethel Grove, Ellis Hollow, Etna, Lacy Corners, Red Mills, Varna, and West Dryden, all lie within Dryden. Other locations include Willow Glen, Malloryville, Smiths Corners, Peruton, Howlands Corners, and Hibbards Corners. The Village of Dryden, located in the Town of Dryden, was incorporated in 1887.