Car Shows – Celebrating Automotive Passion with the Community

Proud Hosts and Supporters of Maryland’s Local Car Culture

At Chesapeake Custom Carriage, we’re more than a vehicle transport company—we’re true car enthusiasts. Our passion for cars runs deep, and we proudly support the local car community by organizing and participating in annual car shows in Sykesville and the surrounding areas.

These events bring together classic car lovers, collectors, builders, and families for unforgettable days filled with horsepower, shine, and community spirit.

Annual Events We Host

🚗 Spring Kickoff Car Show
Our season opener brings together hundreds of local car lovers to showcase classic rides, modern muscle, trucks, and rare finds.

🚙 Fall Cruise-In & Show
An annual tradition that closes the season with great food, live music, raffles, and of course—plenty of chrome and conversation.

Why We Do It

We believe in giving back to the community that fuels our passion. Our car shows are not only a place to show off incredible machines—they’re a way to build friendships, support local causes, and celebrate the craftsmanship and history behind every vehicle.

We’re proud to bring together people of all ages who share a love for everything automotive.

📸 Photo Gallery

Take a look at some highlights from our most recent car show below:

Want to Join the Next Show?

Whether you’re a seasoned collector, a weekend cruiser, or just someone who appreciates a good-looking car, everyone is welcome at our events.