Florida · Race calendar
Upcoming running races in and near Naples, Florida - 5Ks, 10Ks, half marathons and more, with dates, pricing, finish-time stats, start-line maps, and local run clubs to train with.
39 upcoming races · 29 with finish-time stats
Naples racing is shaped by the Gulf at every turn. Training routes hug Gulf Shore Boulevard past beach access points and the Naples Pier, wind through the Moorings on tree-lined residential loops, or duck into the Gordon River Greenway where the foliage goes full Everglades. The flatness that makes the waterfront miles so inviting carries straight into race day.
Heat and humidity are the real course conditions here, which is why the local habit of pre-dawn starts and shaded paths is worth knowing before you sign up. The community converges around Lowdermilk Park and the Old Naples waterfront, so even smaller fields feel like they belong to a place with a genuine running culture.
By the numbers
The Naples races that stand out on the numbers: the biggest field, and the longest unbroken run of editions.
Within 100 miles
More race calendars close to Naples. Miles are measured center to center, so treat them as a rough guide.
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.
Across the 26 Naples 5K editions on RunSesh with published results - walkers and charity entrants included - the median finish time was 34:03, the median winner crossed in 20:08, and the last finisher typically came in around 57:28. The median field size is 21, so these are small, relaxed fields where no one is waiting long and no one is going to disappear into the crowd.
The flat waterfront terrain that defines running here is genuinely forgiving on a first long effort. Fields are intimate - the median half marathon field size across 19 editions with published results is 3 - so expect a quiet, low-pressure atmosphere rather than a big-city spectacle. That suits some first-timers perfectly and unnerves others, so go in knowing the vibe.
Fall, from September through November, is the busiest stretch with 15 races. If you need a specific window, August has the single busiest month with 6 races, while January is the quietest with 1. The calendar runs year-round, so the heat and humidity of summer are a real factor for several of these events, not just training.
Of the 32 races, 10 say they give a shirt and 1 says it gives a medal. The other 21 have said nothing about giveaways at all - that is silence, not a no. If swag matters to your decision, filter for races that have confirmed what they offer rather than assuming the quiet ones come empty-handed.
Yes, one race around Naples gets you off the pavement: 1 is a trail race.
