Above / From fancy to traditional and from themes to centerpieces, organizers of the Jaycees Hack the Jack contest invite pumpkin carvers of all skill levels to enter the competition. (Photo courtesy Naperville Jaycees)

And winners of the inaugural Hack the Jack are #5, #18 and #19

UPDATE, Oct. 28, 2017 / The Naperville Jaycees set up a booth at the Naperville Plaza Fall Festival where they announced each of the winners in the Hack the Jack contest. The pumpkin designed by Paul Arriola received far and away the most votes for first place, said event chairman Bill Donofrio. And two pumpkins designed for KidsMatter came in second and third. The winner of the 50/50 Raffle was David Coyner.

Above / Late in the afternoon Jaycee P.J. Willliams helped present a big check to Paul Arriola for his first prize creation. 

Above / The check for the second and third prizes both went to KidsMatter. When KidsMatter Executive Director Idalynn Wenhold stopped by the pick up winnings for her organization, she couldn’t resist purchasing raffle items on display from Jaycees P.J. Williams and Bill Donofrio.

UPDATE, Oct. 20, 2017 / 23 pumpkins were designed to welcome your votes.

UPDATE! Pumpkins now on exhibit (click here) online!

Original Post, Oct. 16, 2017 / From 4:30 to 9PM this Thurs., Oct. 19, volunteers at Naper Settlement accepted decorated pumpkins for the first-ever Hack the Jack event, the area’s inaugural pumpkin carving contest hosted by the Naperville Jaycees. Event chairman Bill Donofrio welcomed fun-loving types to get together with family and friends, purchase a pumpkin or two or three, come up with a bright idea for a theme, and get carving.

“This contest is designed for the fun of it,” said Donofrio. “Contestants can carve, paint, decorate, cut stencil art—just get together, turn the pumpkin into something original this Wednesday evening and go for the prize this weekend.”

Donofrio said the Jaycees aim to appeal to an audience of all ages with an exhibit of creativity that will attract local residents to vote for their favorite jack o’lanterns all in a row.

Hack the Jack will give contestants the chance to win cash prizes for first, second and third place. The more pumpkins entered in the competition, the higher the cash prizes. Plus, there will be a 50/50 split prize, much like a 50/50 raffle.

Enter a pumpkin for $15 and a chance to win

Designed by The Growing Place for KidsMatter.

The fee to enter a pumpkin in Hack the Jack is $15 per pumpkin. Pumpkins must be brought to the parking lot behind the Martin Mitchell Mansion at Naper Settlement from 4:30 to 9PM on Thurs., Oct. 19.

Every pumpkin entered in the competition must be fully carved and/or decorated prior to submission.

Some restrictions apply. For instance, all entries and winners must be Illinois residents.

Pumpkins now on exhibit (click here) online! 

To participate, area residents must submit jack o’lanterns on Oct. 19 prior to judging by other locals visiting Naper Settlement from Friday, Oct. 20 through Sun., Oct. 22, during normal business hours, and during All Hallow’s Eve at the outdoor history museum.  Photos of the pumpkins also will be featured on the Jaycees website for online voting.

Jack o’lanterns selected as first, second and third will win cash prizes.  Raffle Tickets for voting may be purchased online, too.

Winners will be announced on Sat., Oct. 28, during the annual Fall Festival at Naperville Plaza in front of Language Star, a business located between Casey’s Foods and Oswald’s Pharmacy.

Naper Settlement is located at 523 S Webster Street.

Naperville Plaza is located at 44 W. Gartner Road at Washington Street.

For everything you might want to know about this pumpkin event, visit Hack the Jack.

Now, orange you about set to squash the competition with your original idea?

Naperville Jaycees

Best known for hosting the Last Fling over Labor Day weekend, the Jaycees are Naperville’s Young Person’s organization dedicated to Philanthropy and Volunteerism, and committed to building Naperville’s future leaders. From holiday food baskets to an annual Easter Egg hunt, the Naperville Jaycees help the community by volunteering time, fundraising, helping others, and recognizing outstanding eort of others within the community – and we have fun doing it.