The Upton Chamber in Massachusetts, an earth-covered stone structure 3.4 meters (m) in diameter, with a corbelled stone dome, and a 4.3 m long entrance passageway, is studied with the aim of determining whether optically stimulated luminescence (OSL) dating methods can be used to establish the approximate construction date of the entranceway. Three samples, taken from soil behind the lowest stones in the wall of the entrance passageway, returned OSL ages between 385 and 660 years ago (or from 1625 A.D. to 1350 A.D.; using the year 2011 as the 0 year). One sample, taken below the bottom of the artifact layers in an archeological test pit in front of the chamber entrance, returned OSL ages between 650 and 880 years ago. A modern sample collected from a nearby fluvial channel returned an age between 55 and 175 years. The Upton Chamber OSL sampling results are challenging to interpret because there are mixtures in the samples of both younger and older grains that likely result from human modification, root or soil processes, animal bioturbation (i.e. ants and worms), and/or partial bleaching. The ages were determined using the lowest component of the finite mixture model as applied to a distribution of quartz grains. Further research may enable us to determine whether older components are of anthropomorphic or geological origin.