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Ultramarathons in Orlando & Winter Park (2026-27)

Updated November 4, 2026

2 ultramarathons are coming up in Orlando & Winter Park in the next 90 days; the next is Holiday Five (Five Days, Five Distances to choose from) on Sunday, December 27 in Winter Park. 5 ultramarathons are listed in Orlando & Winter Park for the next 12 months; the next one starts from $30.

All OrlandoOrlando & Winter Park (5)Kissimmee, Clermont & Winter Garden (1)Seminole County & West Volusia (2)

• 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 ↗
• Sat1May

  Sunshine Double (Two Days, Five Distances to choose from)

  Sat May 1 · 6:00 AM · Winter Park · Orlando & Winter Park

  5K10KHalf marathonMarathon50K

  from $30Goes up Apr 23Sign up ↗
• Sat26Jun

  Independence Double (Two Days, Five Distances to choose from)

  Sat Jun 26 · 5:00 AM · Winter Park · Orlando & Winter Park

  5K10KHalf marathonMarathon50KTrail

  from $30Goes up Jun 19Sign up ↗
• Sat4Sep

  Labor Day Triple (Three Days, Five Distances to choose from)

  Sat Sep 4 · 5:00 AM · Winter Park · Orlando & Winter Park

  5K10KHalf marathonMarathon50K

  from $30Goes up Aug 27Sign up ↗

Quick answers

How many ultramarathons are in Orlando & Winter Park in the next 3 months?

2 ultramarathons are listed in Orlando & Winter Park between November 7 and February 5. The next is Holiday Five (Five Days, Five Distances to choose from) on Sunday, December 27 in Winter Park.

What is the cheapest ultra in Orlando & Winter Park right now?

Holiday Five (Five Days, Five Distances to choose from) on December 27 has the lowest listed entry fee in the next 90 days: $30. Prices are before the registration platform's processing fee.

When does the next early-bird price end for ultramarathons in Orlando & Winter Park?

Holiday Five (Five Days, Five Distances to choose from): the 50K goes from $350 to $390 after December 20. 3 more of these ultramarathons publish a later price increase.

Are there ultramarathons in Orlando & Winter Park this weekend?

None are listed for November 7 to November 8. The next is Holiday Five (Five Days, Five Distances to choose from) on Sunday, December 27 in Winter Park.