In 1875, Mike Geary purchased this site and opened Geary's Hotel. What existed before is unknown, but we do know one of the hotel's major attractions was its bar, which was located on the north end of the building.
On October 8, 1878, Mike Geary advertised that "the bar will be stocked with the best liquors, such all pure homemade whiskey and apple brandy, bottled and draft beer, brown stout and porter." In 1892, he proudly announced "the Celebrated Globe Beer is for Sale at Geary's, Here."
The Geary Hotel's bar would operate until alcohol was outlawed in 1907. At the time, the Shenandoah Herald reported only it and the Holtzman Hotel across the street were operating bars. They generated over $500 annually in town liquor taxes, so their business must have been brisk. Lawyers representing the two businesses fought efforts to outlaw alcohol, but they were unsuccessful. The "dry" supporters won by one vote.
After this referendum, the Geary Hotel's bar became a cafe. In the 1930s, Massanutten Military Academy bought the hotel and kept it in operation as the Hotel Woodstock. It closed sometime after 1950. The building became the Walton and Smoot Drug Store in 1968.