How to compete, join the fun at Naperville's Last Fling

  • Try your hand -- or face -- at the annual apple pie-eating contest at 12:30 p.m. Sunday during the Naperville Jaycees' Last Fling festival at the Naper Settlement, 523 S. Webster St. The contest is just one of at least a dozen ways festivalgoers can get involved in lighthearted competitions.

    Try your hand -- or face -- at the annual apple pie-eating contest at 12:30 p.m. Sunday during the Naperville Jaycees' Last Fling festival at the Naper Settlement, 523 S. Webster St. The contest is just one of at least a dozen ways festivalgoers can get involved in lighthearted competitions. Daily Herald file photo

  • Toss a horseshoe or two at 9:30 a.m. Saturday during the Last Fling in downtown Naperville or get involved with other contests including bingo, a super hero race, bed races or water balloon dodgeball.

    Toss a horseshoe or two at 9:30 a.m. Saturday during the Last Fling in downtown Naperville or get involved with other contests including bingo, a super hero race, bed races or water balloon dodgeball. Brian Hill | Staff Photographer September 2009

  • The Nuns on the Run team from St. Patrick's Residence in Naperville is a staple in the annual bed races at the Last Fling in Naperville, scheduled for 11 a.m. Saturday on Porter Avenue south of the Naper Settlement.

    The Nuns on the Run team from St. Patrick's Residence in Naperville is a staple in the annual bed races at the Last Fling in Naperville, scheduled for 11 a.m. Saturday on Porter Avenue south of the Naper Settlement. Daniel White | Staff Photographer September 2011

 
 
Posted9/2/2015 10:00 AM

Attending summer festivals is often a bit of a spectator sport.

Watch bands perform. Admire art. Gaze at carnival rides that make the stomach churn on sight alone and eye some carnival food, but try (and often fail) to steer clear of the funnel cakes and fried Oreos. Even engage in people-watching as crowds gather in all manner of attire to celebrate the season.

 

There will be plenty to see at the 50th annual Last Fling from Friday through Monday in downtown Naperville. But as infomercial pitchmen say, wait, there's more!

To fully enjoy the Fling, don't just watch, but participate in one of 20 quirky contests, cook-offs or unusual races that organizers say are what sets the festival apart.

"We have events for everybody," Special Events Coordinator Helen Taylor said, before beginning a list that actually proves her right.

There's a horseshoe toss contest and a bags tournament for adults, a bingo tournament for seniors, a rib cook-off for grillmasters and an apple pie bake-off for sweet chefs, a four-legged follies competition for people and pet pooches and a CrossFit challenge for exercise enthusiasts.

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On the other end of the age spectrum, there's a diaper derby for crawling babies. For those who've grown up a bit, there's a superhero race for kids, a soccer shootout, a slam-dunk contest and water balloon dodgeball for families. Singers of all ages can test their skill in Singing at the Fling.

New this year are a three-legged race, a Hula-Hooping contest and a limbo contest.

And don't forget the food challenges for those who want to quickly stuff their faces with apple pie, ice cream or spaghetti, sometimes without the use of utensils

"There's definitely a variety depending on what you like and what you want to do," Taylor said.

Some contests require some advanced preparation, like the rib cook-off, the apple pie bake-off or the bed races that challenge groups of five people to decorate a bed on wheels, place the smallest team member upon it and sprint at top speed down a short street.

But most others can be truly spur-of-the moment, with on-site registration beginning 15 to 30 minutes before the fun is set to start.

"It's community-centric," Jaycees member Chad Pedigo, executive director of the 2014 Last Fling, said about the full-participation elements of the fest. "I do think that's one of the things that make it stand apart."

                                                                                                                                                                                                                       
 

In between tossing bags, racing on Big Wheels and belting out pop songs, crowds at the Fling can try their hand at the dunk tank, where members of the Jaycees, the junior chamber organization that plans the fest, as well as school principals and other well-known folks in Naperville will be perched awaiting certain splashes.

"I find it to be amusing and hilarious, so every year I offer my services for the dunk tank," said John Trojanowski, a Jaycees member and this year's Last Fling executive director.

The eating, racing and singing contests have their root in the Fling's beginnings.

Last Fling founder Rick Motta, an 84-year-old barber, said as early as the second year of the festival, he planned a rock 'n' roll competition for local bands as well as watermelon- and pie-eating contests. Early years of the fest also included spirit contests and square dancing exhibitions.

"Those are all things that are like small-town things and that's what I liked about it," Motta said. "It's a small-town contest."

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