About the Fleet Feet Poughkeepsie's 2026 Ugly Sweater Run
This is an untimed holiday run where the outfit is half the point. Runners and walkers show up in their most outrageous sweaters, and prizes go to whoever brings the most creative holiday spirit. Brooks has a setup on course where you can try on a pair of their latest shoes mid-run, which is an unusual touch.
The race is organized out of Fleet Feet Poughkeepsie, so that store is the natural home base for the morning. Beyond the costume competition and the shoe demo, the pace is genuinely open, which makes it a comfortable way to shake out the legs during the holiday stretch.
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