This fundraiser is one that will work well if there's a new prison in your area about to open or an old one that's just been shut down. The idea is that people pay to spend a night in jail, to see what the experience is like. For prison officials, it's a chance to test the facility and see that everything works.
You'll find that the authorities might be grateful for the chance to have a willing group of volunteers flushing all the toilets at once or testing the cafeteria's food to make sure the location is suitable for real prisoners. All of the participants would be issued with authentic prison garb and an inmate number (you could give out commemorative or t-shirts or mug shots too).
For a truly realistic experience, collect up people's personal effects and keep to a prison routine where you can — the “inmates” can spend time in the yard playing games or taking classes from the education staff, for example.
As most prisons are single sex facilities, you may need to make arrangements for separate bathroom and changing facilities if you have both male and female volunteers.
On the morning after, go through the process of a a room check to make sure beds are correctly made and the rooms are clean, then let your prisoners out on parole.
Variation:
This fundraiser is one that will work well if there’s a portable dog pen that can be set up as a jail. The Sheriff and Deputies are able to arrest classmates, teachers or administrators. Then anyone that is has been jailed must be bailed out by friends, coworkers or family for a nominal fee.
People needed-
Jailer
Sheriff
Deputies
Bail Bondsman
NOTE: Get out of Jail Free Cards can be sold that night from the Bail Bondsman.