Pumpkin Run - Oconomowoc, WI

Pumpkin Run - Oconomowoc, WI is held in Oconomowoc, Wisconsin, on October 25, 2026, as part of the Winter Run Series. Two distances start together at 9:00 a.m.: a 10K over 6.2 miles and a 5K over 3.1 miles, and the event is open to runners of every level.

The gap between those two distances is bigger than it looks. A 5K can be carried on sharpness alone, while a 10K needs a base of steady weekly mileage and a long run of 8 to 10 miles behind it, otherwise the fifth mile will find you out. Choose accordingly and pace the 10K about 20 to 30 seconds per mile slower than your 5K effort. Late October in southern Wisconsin means dressing for a cold start and shedding a layer before the gun, and the route takes in the town itself.