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Winter ultramarathons near Orlando (2026-27)

Updated November 4, 2026

5 ultramarathons are on the calendar near Orlando in winter 2026-27, starting with Ancient Oaks 100-Mile Endurance Run on Saturday, December 19 in Titusville. That covers December to February. 2 of them publish an upcoming price increase, so signing up early saves money.

All winter races5K races (81)10K races (33)Half marathons (32)Marathons (10)Ultramarathons (5)Trail races (9)

• Sat19Dec

  Ancient Oaks 100-Mile Endurance Run

  Sat Dec 19 · 7:00 AM · Titusville · Seminole County & West Volusia

  100 milesTrail

  Reg. closed
• Sun27Dec

  Holiday Five (Five Days, Five Distances to choose from)

  Sun Dec 27 · 6:00 AM · Winter Park · Orlando & Winter Park

  5K10KHalf marathonMarathon50KTrail

  from $30Goes up Dec 20Sign up ↗
• Thu7Jan

  Walt Disney World® Marathon Weekend With A Running Passion

  Thu Jan 7 · 5:00 AM · Orlando · Orlando & Winter Park

  5K10K · FriHalf marathon · SatMarathon · Sun39.3 miles · Sat48.6 miles

  from $75Sign up ↗
• Thu7Jan

  Tech Corps Charity Group Registration (2027 Walt Disney World® Marathon Weekend)

  Thu Jan 7 · 5:30 AM · Kissimmee · Kissimmee, Clermont & Winter Garden

  5K10K · FriHalf marathon · Sat39.3 miles · Fri48.6 miles

  from $125Sign up ↗
• Thu18Feb

  Florida Five (Five Days, Five Different Locations, Five Distances to choose from)

  Thu Feb 18 · 8:00 AM · Winter Park, Apopka, Winter Garden, Union Park & Orlando · Seminole County & West Volusia

  5K10KHalf marathonMarathon50K

  from $30Goes up Feb 4Sign up ↗

• Fall 202638 races
• Spring 202757 races
• Summer 202721 races

Quick answers

How many ultramarathons are near Orlando in winter 2026-27?

5 ultramarathons are listed near Orlando in winter 2026-27. The first is Ancient Oaks 100-Mile Endurance Run on Saturday, December 19 in Titusville, and the last is Florida Five (Five Days, Five Different Locations, Five Distances to choose from) on February 18.

What is the cheapest ultra near Orlando in winter 2026-27?

Holiday Five (Five Days, Five Distances to choose from) on December 27 has the lowest listed entry fee: $30. Prices are before the registration platform's processing fee.

When does the next early-bird price end for ultramarathons near Orlando?

Holiday Five (Five Days, Five Distances to choose from): the 50K goes from $350 to $390 after December 20. 1 more of these ultramarathons publish a later price increase.

Are there half marathons or marathons near Orlando in winter 2026-27?

Yes: 4 half marathons and 3 marathons. The first is Holiday Five (Five Days, Five Distances to choose from) on December 27.