The Winter Park Road Race, set for Saturday, March 28, 2026, invites runners to experience the charming streets of Winter Park, Florida. This eagerly anticipated event, marking its 49th annual running, offers both a 10K and a 2-Mile distance, with the exciting "Distance Dare" challenge for those who wish to complete both races and earn three finisher medals. The course is renowned for being scenic and mostly flat, guiding participants through beautiful neighborhoods, tree-canopied roads, and past historic homes and picturesque views of the Chain of Lakes. The 10K route, in particular, meanders along historic brick streets, offering glimpses of landmarks like the Winter Park Country Club and Casa Feliz.

As the grand finale of the esteemed Track Shack Running Series, this race is a cherished local tradition that frequently sells out, a testament to its popularity and the consistently well-organized events by Track Shack. Runners can expect typical race day conditions in late March with comfortable highs around 81°F and lows around 60°F, accompanied by a low 8% chance of precipitation, creating favorable running weather. Beyond the course, participants will be celebrated with gender-specific race tees and impressive finisher medals. The vibrant post-race party on Park Avenue is a highlight, offering beer for those 21 and over, and AdventHealth tents providing valuable runner services like physical therapist assessments and complimentary massages. The scenic beauty and festive atmosphere make the Winter Park Road Race a must-do event for both seasoned runners chasing a personal best on its flat terrain and those looking to enjoy a memorable run through a picturesque Florida town.