PLAINFIELD, IL. — Webb Auto Group is bringing back its annual Ride for the Troops — and this year, it's expanding the event in a big way. On Sunday, May 31st, Webb Auto Group will host the 5th Annual Ride for the Troops at 16140 S. Lincoln Highway in Plainfield, with a new addition this year — a Classic Car Show featuring vehicles of all makes and model years. All proceeds from the event will benefit the United Service Organizations (USO), supporting active-duty service members and their families.

Now in its fifth year, Ride for the Troops continues to grow as a local event that brings together cyclists, veterans, car enthusiasts, and families from across Will County and Chicago's southwest suburbs. Organizers are aiming to raise more than $10,000 this year through rider registrations, car show entries, raffles, and community donations.

The addition of a Classic Car Show — open to all makes and model years — adds a new element to this year's event, making May 31st an even bigger opportunity for the community to come out, connect, and support a meaningful cause.

Event Details

Event Schedule

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 Prizes
• Register:  webbcars.com/events/ride-for-the-troops

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

Supporting Military Families

Proceeds from the event benefit the United Service Organizations (USO), which provides programs and services to active-duty service members, veterans, and their families.

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 donating — every bit of support goes to the USO and the military families they serve.

Register or donate:  webbcars.com/events/ride-for-the-troops

Spots fill up — register early to lock in your event T-shirt (guaranteed through May 20).

About Webb Auto Group

Webb Auto Group is a family-owned automotive dealership group based in Illinois, serving customers across Plainfield, Oak Lawn, Highland, Merrillville, Schererville and the greater Chicago and Northwest Indiana region for more than 50 years. Webb Auto Group operates multiple new and used car dealerships, including Chevrolet, Hyundai, and Genesis locations, and is known for its strong reputation in automotive sales, service, and customer care.

In addition to its automotive business, Webb Auto Group is recognized for its commitment to community involvement, regularly organizing and supporting local events, charitable initiatives, and programs that benefit military families and organizations such as the USO.

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

Webb Chevy Plainfield  |  Plainfield, IL  |  (815) 436-2071  |  webbcars.com  |  Press R