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Winter trail races near Orlando (2026-27)

Updated November 4, 2026

9 trail races are on the calendar near Orlando in winter 2026-27, starting with Core's 2026 Reindeer Run & Roll 5k on Saturday, December 5 in Altamonte Springs. That covers December to February. 7 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)

• Sat5Dec

  Core's 2026 Reindeer Run & Roll 5k

  Sat Dec 5 · 7:00 AM · Altamonte Springs · Seminole County & West Volusia

  5KTrail

  from $35Sign up ↗
• 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 ↗
• Sat16Jan

  Outlast Orlando

  Sat Jan 16 · 8:00 AM · Clermont · Kissimmee, Clermont & Winter Garden

  18 milesTrail

  from $100Goes up Jan 3Sign up ↗
• Sat23Jan

  DeBary 50K, Marathon, Half, 10K & 5K - MileBuilt Gemini Springs 2-Day Challenge

  Sat Jan 23 · 7:00 AM · DeBary · Seminole County & West Volusia

  5K10KHalf marathonMarathonTrail

  from $35Goes up Jan 8Sign up ↗
• Sat6Feb

  Camp Boggy Creek 5K Fun Run and Gravel Ride

  Sat Feb 6 · 8:00 AM · Eustis · Seminole County & West Volusia

  5KTrail

  from $25Goes up Feb 5Sign up ↗
• Sat13Feb

  AdventHealth Lake Apopka Scenic Trail 30K Run, 8 Miler & 5K

  Sat Feb 13 · 7:00 AM · Apopka · Seminole County & West Volusia

  5K8 milesHalf marathon30KTrail

  from $40Goes up Dec 31Sign up ↗
• Sun14Feb

  Tracked Chair Adventures -- Run for the Woods

  Sun Feb 14 · 7:30 AM · Sorrento · Seminole County & West Volusia

  5K7.14 milesHalf marathonTrail

  from $60Goes up Jan 10Sign up ↗
• Sat20Feb

  Winter Park 50K, Marathon, Half, 10K & 5K - MileBuilt Cady Way Bridge 2-Day Challenge

  Sat Feb 20 · 5:00 AM · Winter Park · Orlando & Winter Park

  5K10KHalf marathonMarathonTrail

  from $35Goes up Feb 5Sign up ↗

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

Quick answers

How many trail races are near Orlando in winter 2026-27?

9 trail races are listed near Orlando in winter 2026-27. The first is Core's 2026 Reindeer Run & Roll 5k on Saturday, December 5 in Altamonte Springs, and the last is Winter Park 50K, Marathon, Half, 10K & 5K - MileBuilt Cady Way Bridge 2-Day Challenge on February 20.

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

Camp Boggy Creek 5K Fun Run and Gravel Ride on February 6 has the lowest listed entry fee: $25. Prices are before the registration platform's processing fee.

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

Holiday Five (Five Days, Five Distances to choose from): the 50K goes from $350 to $390 after December 20. 6 more of these trail races publish a later price increase.

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

Yes: 5 half marathons and 3 marathons. The first is Holiday Five (Five Days, Five Distances to choose from) on December 27.