Home / Fort Myers & Naples / Winter 2026-27 / Trail races
Winter trail races near Fort Myers & Naples (2026-27)
Updated
6 trail races are on the calendar near Fort Myers & Naples in winter 2026-27, starting with Ccps 5K & 1 Mile on Saturday, December 5 in Naples. That covers December to February. 6 of them publish an upcoming price increase, so signing up early saves money.
All winter races5K races (54)10K races (15)Half marathons (16)Marathons (2)Trail races (6)
By date
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Sun Jan 3 · 8:00 AM · Alva · Fort Myers & Cape Coral
10 milesTrail
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Sat Jan 30 · 8:00 AM · Bokeelia · Fort Myers & Cape Coral
5KTrail
Other seasons near Fort Myers & Naples
Quick answers
How many trail races are near Fort Myers & Naples in winter 2026-27?
6 trail races are listed near Fort Myers & Naples in winter 2026-27. The first is Ccps 5K & 1 Mile on Saturday, December 5 in Naples, and the last is Picayune 10 Miler on February 13.
What is the cheapest trail race near Fort Myers & Naples in winter 2026-27?
Harns Marsh 5K & 12K on January 23 has the lowest listed entry fee: $32.50. Prices are before the registration platform's processing fee.
When does the next early-bird price end for trail races near Fort Myers & Naples?
Caloosa Fest: the 5K goes from $40 to $45 after November 14. 5 more of these trail races publish a later price increase.
Are there half marathons or marathons near Fort Myers & Naples in winter 2026-27?
Yes: 1 half marathon and 0 marathons. The first is Caloosa Fest on December 6.