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Trail races in Kissimmee, Clermont & Winter Garden (2026-27)

Updated November 7, 2026

3 trail races are coming up in Kissimmee, Clermont & Winter Garden in the next 90 days; the next is The Florida Run @ Lake Louisa State Park on Saturday, November 7 in Clermont. 7 trail races are listed in Kissimmee, Clermont & Winter Garden for the next 12 months; the next one starts from $62.

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• Sat7Nov

  The Florida Run @ Lake Louisa State Park

  Sat Nov 7 · 7:00 AM · Clermont · Kissimmee, Clermont & Winter Garden

  5K10KHalf marathonTrail

  from $62Sign up ↗
• Sat21Nov

  5K with the 5-0

  Sat Nov 21 · 8:00 AM · Oakland · Kissimmee, Clermont & Winter Garden

  5KTrail

  from $20Goes up Nov 8Sign up ↗
• Sat16Jan

  Outlast Orlando

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

  18 milesTrail

  from $100Goes up Jan 3Sign up ↗
• Sat13Mar

  Lssc Shamrock Shuffle

  Sat Mar 13 · 8:00 AM · Clermont · Kissimmee, Clermont & Winter Garden

  1 mile5K10KTrail

  from $15Goes up Jan 4Sign up ↗
• Sun21Mar

  AdventHealth Lake Minneola Half Marathon, 10K and 5K

  Sun Mar 21 · 7:00 AM · Clermont · Kissimmee, Clermont & Winter Garden

  5K10KHalf marathonTrail

  from $39Goes up Dec 31Sign up ↗
• Sat19Jun

  The Florida Run Leftover Trail Race

  Sat Jun 19 · 7:00 AM · Clermont · Kissimmee, Clermont & Winter Garden

  4 miles8 milesTrail

  from $25Goes up Nov 7Sign up ↗
• Sat30Oct

  Nightmare on the Clermont Trails 5K

  Sat Oct 30 · 6:30 PM · Clermont · Kissimmee, Clermont & Winter Garden

  5KTrail

  from $39Goes up Nov 30Sign up ↗

Quick answers

How many trail races are in Kissimmee, Clermont & Winter Garden in the next 3 months?

3 trail races are listed in Kissimmee, Clermont & Winter Garden between November 7 and February 5. The next is The Florida Run @ Lake Louisa State Park on Saturday, November 7 in Clermont.

What is the cheapest trail race in Kissimmee, Clermont & Winter Garden right now?

5K with the 5-0 on November 21 has the lowest listed entry fee in the next 90 days: $20. Prices are before the registration platform's processing fee.

When does the next early-bird price end for trail races in Kissimmee, Clermont & Winter Garden?

The Florida Run Leftover Trail Race: the 4 miles goes from $25 to $30 after November 7. 5 more of these trail races publish a later price increase.

Are there trail races in Kissimmee, Clermont & Winter Garden this weekend?

Yes, 1: The Florida Run @ Lake Louisa State Park (Sat).