Home / Fort Myers & Naples / Winter 2026-27
Winter races near Fort Myers & Naples (2026-27)
Updated
57 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. 34 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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from $40Sign up ↗
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Sat Dec 5 · 8:00 AM · Naples · Naples, Estero & Bonita Springs
5K10KHalf marathonMarathon
from $30Sign up ↗ -
Reg. closed
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from $30Sign up ↗
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Sat Dec 12 · 7:30 AM · Fort Myers · Fort Myers & Cape Coral
1 mile5K
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Sat Dec 12 · 8:00 AM · Naples · Naples, Estero & Bonita Springs
5K10KHalf marathon
from $30Sign up ↗ -
Sat Dec 12 · 8:00 AM · Punta Gorda · Punta Gorda & Port Charlotte
5K10KHalf marathon
from $30Sign up ↗ -
Sat Dec 12 · 8:00 AM · Fort Myers · Fort Myers & Cape Coral
1 mile5K4.1 miles
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Sun Dec 13 · 7:45 AM · North Port · Punta Gorda & Port Charlotte
5K10K
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Sat Dec 19 · 8:00 AM · Naples · Naples, Estero & Bonita Springs
1 mile5K
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Sat Dec 19 · 8:00 AM · Naples · Naples, Estero & Bonita Springs
5K10KHalf marathon
from $30Sign up ↗ -
Sat Dec 26 · 8:00 AM · Naples · Naples, Estero & Bonita Springs
5K10KHalf marathon
from $30Sign up ↗ -
Sat Dec 26 · 9:00 AM · Port Charlotte · Punta Gorda & Port Charlotte
5K
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Thu Dec 31 · 8:00 AM · Naples · Naples, Estero & Bonita Springs
5K10KHalf marathon
from $30Sign up ↗ -
Thu Dec 31 · 5:00 PM · Punta Gorda · Punta Gorda & Port Charlotte
5K
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Sat Jan 2 · 8:00 AM · Naples · Naples, Estero & Bonita Springs
5K10KHalf marathon
from $30Sign up ↗ -
from $30Reg. closed
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Sun Jan 3 · 8:00 AM · Alva · Fort Myers & Cape Coral
10 milesTrail
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from $45Sign up ↗
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Sat Jan 9 · 8:00 AM · Naples · Naples, Estero & Bonita Springs
5K10KHalf marathon
from $30Sign up ↗ -
Sat Jan 9 · 8:00 AM · Punta Gorda · Punta Gorda & Port Charlotte
5K10KHalf marathon
from $30Sign up ↗ -
Sat Jan 16 · 8:00 AM · Naples · Naples, Estero & Bonita Springs
5K10KHalf marathonMarathon
from $30Sign up ↗ -
Sun Jan 17 · 7:00 AM · Naples · Naples, Estero & Bonita Springs
Half marathon
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Sat Jan 23 · 8:00 AM · Cape Coral · Fort Myers & Cape Coral
5K
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Sat Jan 23 · 8:00 AM · Naples · Naples, Estero & Bonita Springs
5K10KHalf marathon
from $30Sign up ↗ -
Sat Jan 30 · 8:00 AM · Naples · Naples, Estero & Bonita Springs
1 mile5K
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Sat Jan 30 · 8:00 AM · Cape Coral · Fort Myers & Cape Coral
5K
from $35Sign up ↗ -
Sat Jan 30 · 8:00 AM · Bokeelia · Fort Myers & Cape Coral
5KTrail
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from $35Reg. closed
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Sat Feb 6 · 7:30 AM · Fort Myers · Fort Myers & Cape Coral
5K
from $20Sign up ↗ -
Sat Feb 13 · 7:30 AM · Naples · Naples, Estero & Bonita Springs
1 mile5K
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Sat Feb 13 · 8:00 AM · Naples · Naples, Estero & Bonita Springs
5K10KHalf marathon
from $30Sign up ↗ -
Sat Feb 13 · 8:00 AM · Punta Gorda · Punta Gorda & Port Charlotte
5K10KHalf marathon
from $30Sign up ↗ -
Sat Feb 13 · 8:00 AM · Port Charlotte · Punta Gorda & Port Charlotte
5K
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from $25Sign up ↗
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Sat Feb 20 · 7:45 AM · Port Charlotte · Punta Gorda & Port Charlotte
5K
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Sat Feb 27 · 8:00 AM · Naples · Naples, Estero & Bonita Springs
5K10KHalf marathon
from $30Sign up ↗
Other seasons near Fort Myers & Naples
Quick answers
How many races are near Fort Myers & Naples in winter 2026-27?
57 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 Squirrel 5K, 10K & 13.1M at Naples, FL (09) on February 27.
What is the cheapest race near Fort Myers & Naples in winter 2026-27?
Justice in Motion 5K & The Honorable Mile on February 13 has the lowest listed entry fee: $10. Prices are before the registration platform's processing fee.
When does the next early-bird price end for races near Fort Myers & Naples?
Caloosa Fest: the 5K goes from $40 to $45 after November 14. 33 more of these races publish a later price increase.
Are there half marathons or marathons near Fort Myers & Naples in winter 2026-27?
Yes: 16 half marathons and 2 marathons. The first is Holiday 5K, 10K, 13.1M & 26.2M at Naples, FL (49) on December 5.