Michael SatterfieldThere are plenty of ways to enjoy a great car, but few are better than pointing it toward an empty Texas back road on a Sunday morning. On September 27, the 2026 Round Top Rally brought together an eclectic collection of sports cars, classics, exotics, and grand tourers for a day built around the simple pleasures that make driving worthwhile: good roads, interesting destinations, great food, and the company of people who would rather take the long way. I would be driving one of Ant Anstead’s Tipo 184 replicas of a 1950s Alfa Romeo Formula car; needless to say, it was going to be a fun drive.
The rally began at The Stella Hotel in Bryan, Texas, where drivers gathered Sunday morning following the previous evening’s Wheels | Watches | Whiskey festivities. By 9:00 a.m., engines were firing, and the parking lot had taken on the unmistakable sound of a proper Sunday drive.
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From Bryan, the route traded highways for the quieter roads of the Brazos Valley and surrounding countryside. The point was never simply to get to Round Top. The road itself was part of the event, and there are some amazing roads in this part of Texas.
Round Top Rally: Three Years In
Community has always been at the center of the Round Top Rally. Texas offers an almost endless network of farm roads, small towns, railroad crossings, rolling hills, and two-lane stretches that are easy to overlook when the interstate promises a faster arrival. But a rally with a group of friends, some old and some made just that morning, makes exploring the back roads even better.
And with everything from vintage machinery to modern supercars making the trip, the scenery in the rearview mirror was often as entertaining as what was ahead (if only the Tipo 184 had usable rearview mirrors).
The first major destination was Henkel Square in Round Top, where participants had time to park the cars and explore one of the town’s most recognizable gathering places. We stopped in and visited our friend Laura Goodson’s art studio, some grabbed a slice of pie from Royers, and everyone enjoyed relaxing and hanging out at the square. Round Top has developed an identity all its own. Part Texas small town, part design destination, part cultural outpost, it attracts an unusual mix of collectors, artists, designers, restaurateurs, and travelers from around the country.
For rally participants, the stop offered a chance to slow down, stretch their legs, grab a coffee, and explore what the town has to offer when the shows are not in season. It was also one of those moments that makes an event like this different from a traditional car show. The cars were not roped off or arranged by class. They had arrived under their own power, carrying a little road dust and bug splatter from the morning’s drive.
Lunch at The Compound
From Henkel Square, the rally continued to The Compound for a private catered lunch. The sprawling Round Top venue provided an ideal place for the field to regroup after the morning drive. Cars filled the grounds while drivers and passengers traded stories from the route, compared notes, and did what enthusiasts inevitably do whenever interesting machinery gathers in one place: walk around and look under the hood.
The lunch stop also reinforced what the Round Top Rally is all about. This is not meant to be a race, and it is not simply a rolling car show. It sits somewhere between a traditional road rally, a Sunday drive, and a Texas lifestyle event. The cars provide the excuse. The experience and the people are the point.
Organizing an open-road rally presents its own challenges. Public roads are still public roads, traffic has its own ideas, and no two drivers have exactly the same definition of the perfect amount of seat time. But that unpredictability is also part of the charm.
Unlike driving around a closed circuit, a road rally unfolds organically. You pass through towns most people normally bypass. You discover roads you did not know existed. You might get separated from the car ahead, catch up with another group twenty miles later, or find yourself following a vintage sports car through a stretch of countryside that looks tailor-made for it.
Those moments cannot really be scheduled. They can only be discovered. Throughout the day, the Satterfield Group media team documented the rally from the road, capturing the cars not just parked at destinations but doing what they were built to do. For many participants, that is the appeal.
Collectors spend enormous amounts of time restoring, maintaining, detailing, and preserving interesting automobiles. Events like the Round Top Rally provide a reason to actually use them.
The Perfect Follow-Up to Wheels | Watches | Whiskey. The rally serves as the second half of a full automotive weekend in Bryan and Round Top. Just one evening earlier, more than 550 guests had gathered at The Stella Hotel and Lake Walk for Wheels | Watches | Whiskey, bringing together cars, watchmakers, whiskey brands, artists, and enthusiasts while helping raise more than $15,000 for OnRamp.
Saturday celebrated the objects enthusiasts collect. Sunday celebrated what cars are really made for: driving. The result is a weekend that feels less like a conventional car show, and more like the sort of gathering enthusiast culture has always been built around: cars, conversation, craftsmanship, food, and a good road disappearing toward the horizon.
As the 2026 Round Top Rally came to an end, plans were already beginning to form for the next one. There will always be debates about the perfect route, the perfect distance, and the perfect number of stops. But next year will be just as special, and I hope you will join us.
