Nov 2 Jail Break 5K, registration and check-in 6:30am-7:15am, race 7:30am. Historic Jail Crown Point, 226 S Main St, Crown Point. 219.775.1981. oldsherrifshouse.org/events. The first annual Jail Break 5K Run and Walk will be held on Saturday, November 2. Benefiting the continuous restoration of the Old Sheriff's House and Jail, this run will take you through the scenic streets of Crown Point Indiana. Starting and finishing at the historic jail, participants will have an opportunity to tour the jail as your registration includes a free tour pass for you on race day.