O.G. Hill started a drugstore on Rapp Street in 1886. He then moved the actual building along with his drugstore to 2530 W. Main St. in 1900. According to historical photographs, a false front had been added to the building around 1911. By about 1927, the Service Drug Store was located here and the façade had acquired the stepped, brick parapet it has today. At that point, the building reflects the commercial construction of the 1920s.

In 1932, store manager T.K. McCain boasted in advertising of “Littleton’s oldest retail store. This drug store was opened 52 years ago (1886) by O.G. Hill.” The drugstore later moved to the Kauer Building, and the building started to house restaurants. Restaurants that called the building home include O’Connell’s Grill (1939), an unnamed restaurant (1953), the Players Lounge (1955–1965), Winners Circle Bar (1966-2011), and Jake’s Beer Garden (2012–present), which added a back garden area and fire pit.

The O.G. Hill Drugstore was incorporated into the Littleton Downtown Historic District as a contributing building on October 26, 2021.  It was listed as a contributing building in the Littleton Main Street National Register of Historic Places District on April 8, 1998.