When are most 5K races held in Kissimmee?
October is the busiest month for 5K races in Kissimmee, with 2 of the 12, followed by November with 2. If you are flexible on the date, that is the quickest way to narrow things down.
Florida · 5K
2026-2027 5K Races in Kissimmee, Florida
Every upcoming 5K around Kissimmee, with start times, entry fees, finish-time stats from past editions, start-line maps, and the local run clubs to train with.
12 upcoming 5K races found · 3 with finish-time stats
By the numbers
The Biggest and Longest-Running
The Kissimmee races that stand out on the numbers: the biggest field, and the longest unbroken run of editions.
Sat, Oct 17, 2026Rise & Run 5K Kissimmee, FLFrom $35Details Fri, Oct 23, 2026Disney Wine & Dine Half Marathon Weekend 2026 Kissimmee, FLRegistration closedFrom $125Details Sat, Nov 14, 2026Victoria Helping Veterans- First Annual Battle Buddy 5k Kissimmee, FLFrom $25Details Sun, Nov 22, 2026Formosa Wine Run Turkey Trot 5k Kissimmee, FLFrom $35Details Sat, Dec 19, 2026Santa Hustle Orlando Kissimmee, FLFrom $60Details Sat, Jan 2, 2027Cheers to New Year's 5k Run/Walk - Orlando Kissimmee, FLFrom $25Details Thu, Jan 7, 20272027 Walt Disney World® Marathon Weekend Kissimmee, FLFrom $125Details Fri, Feb 26, 2027Princess Half Marathon Weekend 2027 Kissimmee, FLFrom $125Details Sat, Mar 6, 2027Keeping PACE with Wellness 5k & Kids Fun Run/Walk Kissimmee, FLRegistration opens Oct 14FreeDetails Sun, Mar 14, 2027Formosa Spiked Apple 5k Kissimmee, FLFrom $30Details Fri, Apr 9, 2027runDisney 2027 Springtime Surprise Weekend Kissimmee, FLFrom $125Details Sat, Sep 25, 20272027 Margaritaville Run Orlando Half Marathon, 10K & 5K Kissimmee, FLFrom $39Details
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 8, 2026.
Common Questions About Running a 5K in Kissimmee
Are Kissimmee 5K races beginner-friendly?
Yes, for the most part. Across the 3 5K races in Kissimmee with published results, the typical median finish is around 46:15, which means half of every one of those fields came in slower than that. Recreational runners and walk-runners are the bulk of these fields, not the exception.
Where can I train for a 5K in Kissimmee?
Browse Kissimmee run clubs on RunSesh to find a training group at your pace.