Saturday was my fifth Middletown Car Show, but it was the first time I entered a car of my own. My 1986 BMW 635CSi joined the line while I did what I have done every other year: walked Main Street with a camera and looked for the moments between the cars.
The 16th annual show brought another mix of classic cars, muscle cars, hot rods, trucks, rat rods, and one-of-a-kind builds into the center of Middletown. The variety is part of what makes it fun to photograph. One frame can be all chrome and careful restoration, and the next can be a wild custom build that makes you stop and work out exactly what you are looking at.
The cars are the reason everyone arrives, but Main Street is what gives this show its character. Storefronts, porches, vendors, neighbors, and visitors all become part of the background. The town is not hidden behind the event. It is in every photograph.
Vault & Cellar is a good example of that relationship. A car passing the restaurant is not just a photograph of a vehicle. It is a photograph of the show happening in Middletown, with a recognizable local business helping place the moment exactly where it belongs.
Five shows in, I still find something different every time. This year it was the small change of being both a participant and a photographer. I had a car in the show, but I kept moving through the crowd, catching details, conversations, and the way the whole street changes when the cars arrive.
That is what keeps me coming back. It is a car show, but it is also a few hours when the town slows down, people wander, and almost every vehicle comes with a story someone is happy to tell.
See all 51 photographs in the complete 2026 Middletown Car Show gallery.