On July 24, 1857, two prisoners in the Dane County jail bribed the turnkey $75 to let them out. Sheriff Bishop, suspicious of the comings and goings of the turnkey, watched the jail that evening and caught them in the act.
Four days later three prisoners - a burglar, a forger, and a horse thief - escaped from the jail by removing the window bar.
The next day the brother of one of the escapees showed up in Madison. He had $50 in gold from the wife of one of the prisoners sewn into his belt to give to the turnkey. He did not know his brother had successfully escaped when he appeared at jail, but confessed he knew the details of the plot. He is now being held.
On August 28, John Perry, the escaped forger, was recaptured in Galesburg, Illinois.
On November 28 the trial of a Winnebago named Dubay for murdering a white man over land at Portage began in Madison. Several criminals in the Dane County jail conspired to break out as the trial began, but the attempt was foiled by Sheriff Welch.
Perry, recaptured in August in Galesburg, apparently escaped again. On December 4 he was discovered and arrested at Rockford, Illinois. He had been jailed there for stealing shingles.