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Joseph Ligon, now 83, was finally freed last week and spoke of his wonder after returning to his home city Philadelphia.
Joseph was just 15 when he was jailed for life in 1953 for taking part in a violent robbery spree.
He walked free last Thursday after judges ruled keeping him locked up was unconstitutional.
Joseph told the Philadelphia inquirer as he gazed at the skyline: “I’m looking at all the tall buildings. This is all new to me. This never existed.”
He is being helped to adjust to his new life by volunteers at Philadelphia's Youth Sentencing & Reentry Project.
John Pace, 52, said he was so overwhelmed he felt sick when he was released from his own life sentence four years ago.
He said of Ligon: "I have been with him in the three days since his release, and I have tried to take it slow with him and allow him to take in the new environment, and not try to figure it all out in one day.
"I have tried to settle his nerves or emotions by helping him to be around familiar people and slowly introduce him to new things."
Ligon was part of a gang of drunk teenagers who went on a robbery and assault spree in Philadelphia that left two people dead and six others stabbed.
He pleaded guilty to murder and admits participating in the crime with others, but denies he killed anyone.
He believes he was scapegoated as the youngest member of the gang and an outsider.
In 2012, a landmark Supreme Court ruling said automatic life sentences for juveniles are cruel and unusual punishment.
After further legal wrangles, in 2017 he was resentenced to 35 years with life parole.
But he rejected parole, saying he should be freed outright with no supervision.
He spent almost four more years in jail while lawyers continued fighting his case.
Finally in November a federal judge ordered him to be sentenced again or released within 90 days, which expired last Thursday. He walked free into a city he barely recognized.
Explaining why he refused an earlier chance at parole he said: “I like to be free.
“With parole, you got to see the parole people every so often. You can’t leave the city without permission from parole."That’s part of freedom for me.”
To prepare himself for modern society, he watched world news on a small TV in his cell.
“I like my chances. I really like my chances in terms of surviving,” he said.
His only regret is that his mother, father, and brother did not live to see his release.