Would recommend using the grandstand to raise money for it.
My brother is a demo derby fanatic and I think this would be a great way to incorporate the grandstand and get the guys involved as well! The fair does offer demo derby as well and they make a ton of $$$! Other ideas
Dirt bike races
Carnival with rides
50/50 raffle at all the events
Brat sale or pulled pork and bake sale
Would culver's help by doing a portion of sales a day go to the grandstand? Or maybe a ice cream social
A bike night (a motorcycle event/meet) bikers are a huge group of lively people with big hearts and this would be a great way for them to get involved.
Comedy night if a local place would offer a large space. Hire a known comedian like Comroe (he was on America's got talent & I've followed him for years prior from his debut on TV) and sell tickets.
Golf a thon at the country club
Participants become your fundraisers by asking for pledges and raising money from their friends and family to sponsor them in the event. This harnesses the power of friendly competition amongst the participants, which usually results in more donations.
Do our own American Idol or dancing with the stars night ?
Movie night at the fairgrounds?
Halloween haunted house at the fairgrounds. Get the schools and kids involved in helping. People LOVE Halloween and will pay good money for entertainment
I personally travel all over Wisconsin for haunted houses. I also have hundreds of Halloween props and decorations.
Petting zoo at the fairgrounds and have many games for kids. Like pick a duck, balloon dart game, ping pong balls in fish bowls for gold fish.... Charge per game have cheaper prizes that maybe could be donated by business?
Use a goal thermometer 🌡️ to post somewhere very visual to keep it on people's mind
Come up with a portage coupon book to sell with offers from Portage and surrounding area businesses
Adult prom night and have a photographer. Charge for entrance and they get a free emailed photo of them from the party
Maybe do a costume contest with the Halloween haunted house
These are just some ideas running thru my head as I type. I hope this helps and maybe we can build off of these ideas!?