What race distances can I run in Winter Park?
Winter Park has 5K (5), 10K (5), Half Marathon (5), Marathon (5), Ultra (5). The 5K is usually the easiest entry point if you are new, and the links above jump straight to each distance.
Florida · Race calendar
Running Races in Winter Park, Florida
Upcoming running races in and near Winter Park, Florida - 5Ks, 10Ks, half marathons and more, with dates, pricing, finish-time stats, start-line maps, and local run clubs to train with.
5 upcoming races
Sat, Sep 5, 2026Labor Day Triple Winter Park, FLFrom $30Details Sun, Dec 27, 2026Holiday Five Winter Park, FLFrom $30Details Sat, Feb 20, 2027MileBuilt 2-Day Bridge Challenge Winter Park, FLFrom $35Details Sat, May 1, 2027Sunshine Double Winter Park, FLFrom $30Details Sat, Jun 26, 2027Independence Double Winter Park, FLFrom $30Details
How we calculate these stats: RunSesh calculates these figures from the most recent published results of past editions, sourced from RunSignup. We show aggregates only: field size, winning and median times, and the cutoff. We never publish individual finisher tables. Last updated Jul 27, 2026.
Common Questions About Racing in Winter Park
How early should I register for a race in Winter Park?
5 of the 5 races in Winter Park already have a price increase scheduled, so entry gets more expensive the longer you leave it. Race pricing almost always steps up as the date approaches, and signing up early is usually the cheapest option.
Where can I train for a race in Winter Park?
Browse Winter Park run clubs on RunSesh to find a training group at your pace.