In 1875, Mike Geary purchased this lot in downtown Woodstock and opened Geary's Hotel. What existed before is unknown.
The three-story brick hotel featured accommodations for travelers, large front portions over looking the valley turnpike, a dining room, and a popular bar 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."
An August 14, 1900 fire gutted the hotel and a portion of the business block where it stood. Geary rebuilt the structure and once again became a thriving business. During the renovations, the hotel operated out of the neighboring Koontz building.
When Woodstock debated outlawing alcohol purchases in 1907, the Shenandoah Herald reported the Geary and the Holtzman Hotel across the street were operating bars that earned the town over $500 annually in liquor taxes. Despite the profitability of alcohol sales here and efforts by the hotels’ legal teams, the town went dry that year and the bar at the Geary became a Café.
In the 1930s Massanutten Military Academy purchased the hotel and renamed it Hotel Woodstock. It continued to cater to travelers visiting the area, but also welcomed official academy guests and parents. They also developed the hotel’s dining facilities, making its banquet hall a central community meeting place. Changes including removal of the large porches, instillation of several balconies, and plumbing.
Sometime after 1950 the Hotel closed as travelers’ tastes turned away from older, large hotels in favor of new auto courts and motels. In 1968 the building was remodeled and became home to Walton and Smoot Drug Store which remained open until 2019. It still stands in Downtown Woodstock.