Aspiration Christmas Wine Run 5k

Aspiration Christmas Wine Run 5k is held at Aspirations Winery in Clearwater, Pinellas County, Florida, on December 19, 2026, with the 5K starting at 9:00 a.m. It is a timed race that can also be walked, set on winery grounds and paired with wine tasting afterward. Entry includes a cotton t-shirt, a wine glass, a complimentary pour, and a finisher medal that doubles as a bottle stopper.

The format is deliberately relaxed, but the clock is real, so it works for both ends of the field: race it as a hard 3.1 miles if you want a time, or walk it with friends and treat the tasting as the point. Four to six weeks of regular running is plenty of preparation. If you plan to enjoy the wine, eat something at the finish before you start on the glass.