The Surprise Shop, founded in 1951, is the direct predecessor of the Hospitality Shop. Bi-annual sales, sponsored by the Children's Aid League, took place in Winchester to raise money for the Emerald-Hodgeson Hospital's Children's Wing. 

The Hospitality Shop opened in the Crockett House (also known as Idlewild) in the winter of 1968, where it lived for the next fifty years. Beloved for its weekly luncheons, the house was the center of Sewanee's community, boasting a tea room, thrift shop, and gift shop. In 2006, the Shop transitioned into a traditional thrift store, focusing on providing affordable goods to raise money for its scholarship program. 

In March of 2026, after a multi-year search, the Hospitality Shop moved to its new location in the previous University childcare center. In particular, this space has ample room for donation intake and sorting, allowing the Shop to more effectively move and sell goods.