Schuyler County Sheriff Josh Dole reportedly brought some inmates to a Knox County bar and another inmate to watering hole in Sullivan County. He is also accused of bringing two inmates to his house to do work at his home, KTVO reported.
Dole wrote that "the events of the past couple of weeks" made him decide to step down in "the best interests of Schuyler County."
The sheriff wrote that he would be resigning "with a heavy heart."
He is charged with three counts of permitting escape and two charges of tampering with a witness for allegedly telling jail personnel members not to discuss the details of the case.
Dole's resignation is effective on July 31. He took office in January 2013.