Published August 28, 2025

History of Naperville's "Last Fling"

Written by Kristen Jungles

The Story of Naperville’s “Last Fling”: From One Parking Lot to a Citywide Send-Off to Summer

If you’ve spent a Labor Day weekend in Naperville, you’ve felt it: the hum of rides along Jackson Avenue, the sound of live music echoing off the Riverwalk, and the Monday morning parade rolling through downtown. That’s the Naperville Jaycees’ Last Fling, a tradition that’s been closing out summer here since the mid-1960s.

How it all started (1966)

Local barber and Chamber of Commerce board member Rick Motta pitched the idea after seeing the movie Picnic: a
community festival and Labor Day parade to cap the season. The first “Last Fling” debuted in 1966, with a parade and a modest picnic set up in the Centennial Beach parking lot.

As enthusiasm grew, Motta chaired the Chamber’s Last Fling committee for six years, helping the event spread from a small gathering into a multi-day celebration.

Rick Motta awarded a trophy for the winning float to Bev Frier in 1966

Handing the baton to the Jaycees

In 1981, the Naperville Area Chamber of Commerce passed organizing duties to the Naperville Jaycees. Under the Jaycees, Last Fling evolved into a four-day, block-style festival anchored in and around downtown, complete with multiple music stages, a carnival, a business expo, and family activities.

A festival with purpose

Beyond the fun, Last Fling is the Jaycees’ largest annual fundraiser. Proceeds are distributed to nonprofits serving Naperville and the surrounding area, a tradition of local philanthropy that’s as central to the event as the Ferris wheel. (lastfling.org)

Signature moments

Labor Day Parade: The capstone of the weekend, stepping off Monday morning through downtown Naperville.
Live music & midway: Bands across multiple stages and a classic carnival vibe along the Riverwalk and Jackson Avenue.
Family Fun Land & community showcases: Hands-on activities for kids, plus local organizations and businesses on display.

Recognition on the national stage

The celebration has earned wider notice, landing on a list of the Top 100 Labor Day celebrations in the U.S. in 2024. Not bad for a party that started in a parking lot.

Last Fling today

Today’s Last Fling fills the long weekend, Friday through Labor Day, with concerts, food, rides, and community spirit centered near the Riverwalk and Jackson Avenue. It remains a joyful “last hurrah” before fall routines return and a fundraiser that channels that energy back into local causes.

We hope the Last Fling brings back some great memories and creates some new ones for you,
friends, and family.

Fun Fast Facts (at a glance)

First year: 1966
Founding spark: Rick Motta, inspired by Picnic, proposed a Labor Day festival & parade
Organizer since 1981: Naperville Jaycees
When: Labor Day weekend (four days)
Where: In and around downtown Naperville/Riverwalk & Jackson Avenue

Why it matters: Proceeds benefit local nonprofits

Past Musical Guests by Year:

Year & Notable Performers