Webb Auto Group to Host 5th Annual Ride for the Troops
Charity Bike Ride & Classic Car Show — Sunday, May 31
Plainfield, Illinois charity event on May 31, 2026 aims to surpass $10,000 raised for military families through the USO — now featuring a Classic Car Show
PLAINFIELD, Ill. — Webb Auto Group is bringing back one of Plainfield’s favorite community traditions — and this year, it’s bigger than ever. On Sunday, May 31, Webb Chevy Plainfield will host the 5th Annual Ride for the Troops, a charity bike ride and brand-new Classic Car Show at 16140 S. Lincoln Highway, Plainfield, IL. Every dollar raised goes directly to the United Service Organizations (USO), supporting the men and women who serve our country.
Five years in, Ride for the Troops has earned its place as one of the most looked-forward-to events on the Plainfield calendar. Cyclists, veterans, car enthusiasts, and families come out from across Will County and the southwest suburbs of Chicago — and each year, the crowd grows. This year’s goal is to top $10,000 raised for the USO, built through rider registrations, car show entry fees, raffle proceeds, and the generosity of the community. With the addition of a Classic Car Show open to all makes and model years, May 31 is shaping up to be the best one yet.
EVENT DETAILS
What: Ride for the Troops — 5th Annual Charity Bike Ride & Classic Car Show
When: Sunday, May 31, 2026
Time: Registration & Car Show Arrival: 9:30 a.m. | Ride Start: 10:30 a.m.
Where: Webb Chevy Plainfield, 16140 S. Lincoln Hwy, Plainfield, IL
Benefiting: United Service Organizations (USO) — 100% of proceeds donated
Register: Sign Up to Ride | [email protected]
ROUTES FOR ALL EXPERIENCE LEVELS
Whether you’re a first-time rider or a seasoned cyclist, there’s a route for you:
- 10-Mile Route — A scenic ride through downtown Plainfield, perfect for families and casual riders
- 20-Mile Route — Challenges more experienced cyclists through the surrounding countryside
Both routes start and finish right at Webb Chevy Plainfield, so there’s no shuttle or logistics to worry about — just show up, ride, and stick around for the fun. Helmets are required. The event is co-presented with TREK Bicycle Stores of Naperville and Downers Grove.
CLASSIC CAR SHOW
This year, the ride comes with a bonus — and car lovers are going to love it. The inaugural Classic Car Show runs alongside the bike ride, giving classic vehicle owners a chance to show off their pride and joy while supporting a great cause. All makes, all years, all welcome.
- Arrival & Registration: 9:30 a.m.
- Open to: All Classic Makes & Model Years
- Entry Fee: $25 per vehicle (100% of proceeds donated to the USO)
- Awards: 1st, 2nd, and 3rd Place trophies
- Register: Sign up Your Car (scan QR code at the event)
Register by May 20 to guarantee your event T-shirt.
COMMUNITY ACTIVITIES & ENTERTAINMENT
The ride and car show are just the beginning. Once you cross the finish line, there’s plenty of reason to hang around:
- Food from Windy City Burger
- Live music from School of Rock
- Military vehicle displays, including U.S. Marine Corps Humvees
- Opportunities to meet and interact with active-duty service members
- Charity raffles: 50/50 split-the-pot, TREK bicycle giveaway, Webb swag, and sponsor donations
WHAT PARTICIPANTS RECEIVE
- Custom Event T-Shirt (guaranteed with registration by May 20)
- Webb Swag Pack
“This started as a smaller ride, and it’s grown each year because people in this community want to be part of it. You see families riding together, veterans coming out, and local businesses supporting it — it’s turned into something people really look forward to.”
— Tim Gehr, General Manager at Webb Auto Group
“This event is something we care deeply about as a company and as a family. It’s grown every year because the community shows up — whether that’s riding, volunteering, or donating. It’s a great way for people to come together and support military families in a meaningful way.”
— Jackie Webb Hibner, Webb Auto Group
HOW TO PARTICIPATE
You don’t have to be a serious cyclist to be part of this. Whether you’re riding, showing your car, cheering from the sidelines, or simply making a donation — every bit of support goes to the USO and the military families they serve.
About Webb Auto Group
Webb Auto Group is a family-owned dealership group serving Illinois and Northwest Indiana for more than 50 years, operating Webb Chevy Oak Lawn, Webb Chevy Plainfield, Webb Hyundai Highland, Webb Hyundai Merrillville, and Genesis of Merrillville. The company is known for its deep community involvement and regularly hosts charitable events that support local organizations and military families. Serving Plainfield, Joliet, Naperville, Bolingbrook, Mokena, and the greater Chicago southwest suburbs.
More information: webbcars.com
About the USO
The United Service Organizations (USO) strengthens America’s military service members by keeping them connected to family, home, and country throughout their service. The nonprofit operates hundreds of locations worldwide and provides programs and services that support troops and their families.
More information: uso.org
Make a donation: Donate to USO
MEDIA CONTACT
Webb Marketing
[email protected]
708-761-2016
Webb Chevy Plainfield | Plainfield, IL | (815) 436-2071 | webbcars.com