It is estimated that almost 40 escape attempts were made over the 150 years but most of them failed. As research stands it shows that 5 men who escaped from Maitland Gaol where never captured, all of these escapes took place within the first 50 years of the Gaol’s operation. For most of those who did get over the walls they were caught within days.
Raymond "the running man” Denning and 6 others escaped through an exhaust vent in the shower block. Within 2 hours of their escape, they were back inside after a massive police swoop on the area.
A 5.5m long tunnel was discovered in Cell 7 in C Wing. An inmate was hiding it with a sheet of plastic painted the same colour as the floor. Once it was discovered, the tunnel was filled in with two truckloads of concrete.
The infamous Ivan Milat and George Savvas had planned an escape from Maitland Gaol in May 1997. Fortunately the staff had gotten wind of the alleged plot and it was thwarted before it even began. Sadly the day after the escape was meant to take place George Savvas was found dead in the cell he had been moved to, this death was the last death in custody in Maitland Gaol and was determined by the coroner as suicide.