Mayor of the North Pole Bob Dautrieve—described by Running of the Santas spokesman Matt Willard as “a guy in his 80s who likes to party”—first witnessed the charitable celebration’s carousing Christmas cheer while visiting its first host city, Philadelphia.

“It started there in 1998 with 40 guys and girls who came up with the idea to go bar hopping in Santa costumes,” Willard tells OffBeat. “It grew word-of-mouth among friends to the event it is today, attracting 10,000 people every year. ...