15 Prisons With The Most Escape Attempts
Prison walls and razor wire exist for one simple reason: keeping dangerous people locked away from society. Yet throughout history, inmates have proven remarkably creative when it comes to breaking free from even the most secure facilities.
Some prisons have earned notorious reputations—not just for housing dangerous criminals, but for the sheer number of escape attempts launched from within their walls. From elaborate tunnel systems to violent riots masquerading as breakouts, these correctional facilities have witnessed everything imaginable in the pursuit of freedom.
Though security has improved dramatically over the decades, these institutions remain infamous for their escape histories. Here is a list of 15 prisons that have experienced the most escape attempts throughout their operational histories.
Colditz Castle
This medieval German castle became legendary during World War II as an ‘escape-proof’ prisoner-of-war camp. Despite its fearsome reputation, Colditz witnessed over 300 escape attempts during the war years.
Remarkably, about 130 prisoners actually succeeded in breaking free—making it one of the most escape-prone facilities in wartime history.
San Quentin State Prison
California’s oldest prison has been dealing with escape attempts since opening in 1854. That first year alone saw more than 80 prisoners break out due to lax security under private management—a staggering number for any facility.
The prison gained lasting infamy for the 1971 San Quentin Six incident, where six inmates attempted a violent escape that left six people dead, including revolutionary George Jackson.
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Alcatraz Federal Penitentiary
Despite being surrounded by frigid waters and marketed as escape-proof, Alcatraz saw 36 men attempt 14 separate escapes between 1934 and 1963. The most famous attempt occurred in 1962 when Frank Morris and the Anglin brothers vanished without a trace—their fate remains unknown to this day.
Either a spectacular success or deadly failure, depending on who you ask.
Folsom State Prison
Johnny Cash made this California prison famous with his song, though Folsom earned its reputation through numerous escape attempts long before that. The first recorded attempt happened in 1880, just after opening its doors.
The facility’s imposing granite walls—built in the 1920s using stone quarried on-site—were specifically designed to prevent the frequent breakouts that plagued its early years.
Attica Correctional Facility
New York’s Attica became synonymous with prison violence after the 1971 uprising that claimed 43 lives. While technically not an escape attempt, the four-day riot involved over 1,200 inmates taking control of the facility—a massive security breach by any measure.
The incident highlighted ongoing problems and inspired copycat attempts at other facilities nationwide.
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Punta Carretas Penitentiary
This Uruguayan prison experienced what many consider the largest escape in history when 111 political prisoners tunneled their way to freedom in 1971. The escapees dug a 45-meter tunnel over several months—with future president José Mujica among those who successfully fled.
The mass breakout embarrassed authorities while demonstrating the power of organized prisoner coordination.
Clinton Correctional Facility
Known as ‘Dannemora,’ this maximum-security New York prison made headlines in 2015 when two convicted murderers escaped through elaborate tunnel systems. David Sweat and Richard Matt spent months cutting through steel walls and pipes with tools smuggled by a prison employee—a painstaking operation that went undetected for far too long.
Their three-week manhunt captivated the nation before both were captured.
Fort San Cristóbal
Built inside a Spanish mountain, this facility seemed escape-proof until May 22, 1938. During the Spanish Civil War, about 30 prisoners organized a massive breakout involving 792 inmates—an unprecedented coordinated effort.
Only three reached the French border successfully, while 585 were arrested and 211 died in the attempt.
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Louisiana State Penitentiary (Angola)
Angola’s reputation as ‘The Bloodiest Prison in America’ includes numerous escape attempts throughout its troubled history. The sprawling facility—built on a former plantation—has witnessed regular breakouts that often end violently.
Its remote location in the Mississippi Delta provides natural barriers, yet inmates continue attempting to flee the harsh conditions.
Cowra POW Camp
This Australian facility experienced one of the largest prisoner-of-war breakouts in history on August 4, 1944. At least 545 out of 1,004 Japanese prisoners attempted to escape in a coordinated effort that shocked authorities.
The violent breakout resulted in 231 deaths and 108 wounded among the escapees—many choosing death over recapture.
Camp 14 (Doonfoot)
Located in Scotland, this World War II prisoner-of-war camp saw 97 Italian prisoners escape on December 15, 1944. The mass breakout occurred after the Italian government switched sides in the war, leaving fascist prisoners feeling abandoned and desperate.
Most were eventually recaptured, but the incident highlighted challenges of managing ideologically motivated inmates.
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Makala Central Prison
Congo’s largest prison recently experienced chaos when hundreds of inmates attempted a mass escape in September 2024. The suppressed attempt resulted in 129 deaths from gunfire and stampeding.
This incident reflects ongoing security challenges in overcrowded African correctional facilities where desperate conditions drive frequent escape attempts.
Rawson Prison
This Argentinian facility became famous in 1972 when six political prisoners not only escaped but hijacked a plane to Chile. The elaborate plan involved multiple stages of coordination and outside assistance.
Though successful, it highlighted the international nature of political prisoner networks during South America’s turbulent political period.
Rikers Island
New York’s notorious jail complex has dealt with countless escape attempts over the decades. The facility’s location on an island provides natural barriers, yet inmates have tried everything from swimming to smuggling themselves out in delivery trucks.
Gang violence and overcrowding create constant tension that often manifests in breakout attempts.
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Soledad Prison
California’s Correctional Training Facility has experienced numerous escape attempts, including several involving the famous Soledad Brothers. The facility’s connection to George Jackson and other radical prisoners made it a hotbed of escape plotting during the 1960s and 70s.
While security improvements have reduced successful attempts, the prison remains challenging to manage.
From Desperation to Legacy
These prisons represent more than just failed security measures—they tell the story of human determination against seemingly impossible odds. Modern technology and improved procedures have made escapes rarer, though the ingenuity displayed in these historical attempts continues to fascinate and inform current correctional practices.
The legacy of these facilities serves as a reminder that the desire for freedom can drive people to extraordinary, sometimes tragic lengths.
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