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, the festival brings together some of the best things about a Round Top weekend: beautiful countryside, good food, live music, shopping, and, of course, plenty of wine and whiskey. The weekend is filled with tastings and events throughout town, making it a fun way to explore Round Top.
From an intimate Friday evening dinner and live music at Zapp Hall to Saturday’s Wine + Whiskey Trail, classic cars, cigars, and tastings, there’s something happening around every corner. And after a full day of sipping and exploring, Sunday brunch is the perfect way to wind down before heading home.
We’d love to be your home away from home, you’ll have plenty of time to enjoy the festivities and a cozy place to come back to after a full day in town.
Round Top in the fall is something special, bring your friends, pick your pour, and make a weekend of it.