When are most half marathons held in Winter Park?
May is the busiest month for Half Marathon races in Winter Park, with 2 of the 6. If you are flexible on the date, that is the quickest way to narrow things down.
Florida · Half Marathon
2026-2027 Half Marathons in Winter Park, Florida
Every upcoming Half Marathon around Winter Park, with start times, entry fees, finish-time stats from past editions, start-line maps, and the local run clubs to train with.
6 upcoming half marathons found
Sun, Dec 27, 2026Holiday Five (Five Days, Five Distances to choose from) Winter Park, FLFrom $55Details Sat, Feb 20, 2027Winter Park 50K, Marathon, Half, 10K & 5K Winter Park, FLFrom $60Details Sat, May 1, 2027Sunshine Double Winter Park, FLFrom $55Details Sat, May 29, 2027Winter Park 50K, Marathon, Half, 10K & 5K Winter Park, FLFrom $60Details Sat, Jun 26, 2027Independence Double Winter Park, FLFrom $55Details Sat, Sep 4, 2027Labor Day Triple Winter Park, FLFrom $55Details
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 Oct 25, 2026.
Common Questions About Running a Half Marathon in Winter Park
Where can I train for a Half Marathon in Winter Park?
Browse Winter Park run clubs on RunSesh to find a training group at your pace.