The stubborn fire sparked on the morning of May 17, 2013, in a building that sits along Washington Street off the courthouse square.
Nearly 100 firefighters from 18 departments battled the blaze that caused an estimated $1.5 million in damages, Mayor Sue Murray said.
"It was huge. Anytime you have a historic downtown and if you suddenly lose four buildings in it, it's a tremendous hole. We've had those holes in the past and they are difficult to take care," Murray said.
Wilson's Photography was one of the businesses that took a hit, even though owner Lester Wilson said it took some convincing.
"It took some persuasion. I was ready to quit, quite honestly. I wanted to dump the building and move on to something else," Wilson said.
Despite the odds, Wilson stayed along with fellow businessman Dentist Perry Wainman.
"With a lot of insurance and local construction people, they were able to put it back together like it was," Wainman said.
Murray said Greencastle is using $19 million in state grants to beautify and redevelop its downtown.