Round Top Wine + Whiskey Weekend 2026
Paige Hull
There’s one thing Round Top does exceptionally well, it’s giving us all a reason to gather, and Round Top Wine + Whiskey Weekend is a fun way to experience the town, especially for wine and whiskey enthusiasts.
Taking place October 2–4, 2026, the weekend brings together some of the best things Round Top has to offer: beautiful countryside, good food, live music, shopping, classic cars, and, of course, plenty of pours worth savoring. Events and tastings unfold throughout town all weekend, making it a unique way to explore Round Top.
It kicks off Friday evening with an intimate candlelit dinner and live music at Zapp Dance Hall. Saturday opens up into a full day of the Wine + Whiskey Trail, classic cars, cigars, and tastings around every corner. And by Sunday, a leisurely brunch before the drive home feels like a great way to close it all out.
We’d love to be your home base for all of it - a cozy place to settle into, exhale, and come back to after a full day in town. Fall in Round Top is something truly special. Bring your people, pick your pour, and make a weekend of it.