Woodruff Hotel once operated from the middle of the block on the south side of the Gallatin business square:

Woodruff Hotel building (1899) on the south side of the Gallatin business square, shown in this 1907 post card. Businesses shown include Harding’s Big Racket, Woodruff Hotel, and Henry’s Meat Market.

The Woodruff Hotel issued tokens to train travelers for rides from the train depot to the Woodruff Hotel on the Gallatin business square. These tokens were first made of aluminum and later of green or red plastic.

In 1910 fire gutted the Woodruff Hotel, located on the south side of Gallatin’s business square.

Reconstruction of the Woodruff Hotel building assured its continued use during ensuing years.