Wheels Watches Whiskey & Round Top Rally: A Tradition In The Making

When we first imagined Wheels Watches Whiskey®, the vision was simple: bring together people who appreciate the finer things, cars, timepieces, and good whiskey, in an atmosphere that feels as authentic as it is elevated. In September 2025, that vision came alive again at The Stella Hotel and Lake Walk for the 4th year, with an unforgettable weekend firmly establishing this as an annual The Gentleman Racer event. Partnering with McLaren North America, GFG Wealth Advisors, five watch brands, eight distilleries, and over 70 vehicles, it was a weekend to remember.

Wheels Watches Whiskey®

Saturday Wheels Watches Whiskey transformed The Stella Hotel and Lake Walk into a curated gallery of motion and design. McLarens, Shelbys, and Porsches parked alongside vintage racing icons, while collectors and enthusiasts admired not only the cars but also the craftsmanship of watchmakers, jewelers, and artisans who joined us.

Some of the highlights from the automotive showcase include a Singer Porsche, a Mercedes Gullwing, and an original Shelby 289 Cobra. But it wasn’t just about sports cars this year. The addition of the Overland Department, featuring custom builds by Helderburg, Vigilante 4X4, and Current EV, brought a new dimension to the Pavilion.

For the watch enthusiasts, Bulova showcased its latest release, the Shelby Racer Chronograph, and local Tudor Authorized Dealer David Gardner’s Jewelers was on hand. Seiko, Seaholm, and vintage watch retailer The Watch Preserve were also on hand, giving shoppers a wide variety of options. One attendee who brought their teenage son purchased his first watch, a Seiko, at the event, proudly posing for his first wrist shot. This year also marked the addition of automotive art featuring three artists with unique interpretations of car culture.

For the whiskey lover, there was a lot to explore, from established leaders like Garrison Brothers and Still Austin to newcomers like Bakalian Family Distilling and Unreined Bourbon. Over eight brands were available for tastings; many had bottles in the Silent Auction benefiting OnRamp.

But this event is more than a spectacle. Through the support of our guests and partners, we raise funds for OnRamp Texas, helping local families gain reliable transportation. It’s proof that passion, when channeled collectively, can leave a lasting impact beyond the show field.

The Round Top Rally™

Sunday morning, engines fired to life for the second annual Round Top Rally™, a drive hosted by The Gentleman Racer that embodies everything we love about cars and culture. From the start line at The Stella Hotel, a convoy of classics, sports cars, and modern exotics carved their way through backroads and farmland, celebrating the joy of driving.

The destination? Round Top is a small Texas town that has become a cultural hotspot thanks to its twice-annual antique shows that draw buyers and sellers from around the world. After a spirited drive, guests sat down at Royers Café for a lunch that blended small-town charm with big-flavor tradition before enjoying a meet and greet and gallery tour with artist Laura Goodson. The group then headed over to Junk Gypsy to enjoy the shade, a cold drink, and a special gift. The rally was more than a drive; it was a shared experience that capped the weekend with the same balance of sophistication and adventure that defines The Gentleman Racer.

Wheels Watches Whiskey & Round Top Rally: Next Year…

What stood out this year was the balance: the spectacle of cars and craftsmanship paired with meaningful community impact. The event grew in size and prestige without losing the intimacy that makes it special.

Wheels Watches Whiskey® has quickly become more than a one-off gathering; it’s a The Gentleman Racer tradition. Each September, we will host a weekend where passion for cars, culture, and connection takes center stage. With the Round Top Rally as its crowning chapter, the annual event is already carving its place in the calendar for enthusiasts who value the drive as much as the destination.

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