Trail Runs in Florida — 2026

There are 31 trail runs in Florida scheduled for 2026. The next is the Operation Outdoor Freedom Event in Middleburg on October 18. Florida trail runs run primarily October through June.

Operation Outdoor Freedom Event

Sun, Oct 18 · Middleburg, FL Middleburg

5 Mile Ruck5 Mile Trail Run10 Mile Ruck +1

From $45 Open Closing Soon 25 spots left

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Newfield - Trick or Trot Trail Run

Sat, Oct 24 · Palm City, FL Palm City

Newfield - Trick or Trot Trail Run

From $40 Open

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The Ainger Creek Trailblazer 5K

Sat, Oct 24 · Englewood, FL Englewood

The Ainger Creek Trailblazer 5K

From $30 Open Closing Soon

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Gopher Weedon Trail Run

Sat, Oct 24 · Saint Petersburg, FL Saint Petersburg

8K Trail Run

From $45 Open Closing Soon

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Greenway Trick 'R Trot

Sat, Oct 24 · Ocala, FL Ocala

5k Run5k Ruck10k Ruck +3

From $35 Open

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Trick-or-Trot 5K Trail Run

Sat, Oct 24 · Palm City, FL Palm City

5K Trail Run

From $45 Open Closing Soon

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The Florida Run @ Lake Louisa State Park

Sat, Nov 7 · Clermont, FL Clermont

5k10KHalf Marathon

From $35 Open

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DTR 10 Mile Night Run

Sat, Nov 21 · Hobe Sound, FL Hobe Sound

DTR 10 Mile Night Run

From $85 Open

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Shut Up and Run 5K

Thu, Nov 26 · Saint Augustine, FL Saint Augustine

Shut Up and Run X-C 5K Race

From $35 Open

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Trail Hog Half Marathon

Sat, Nov 28 · Venice, FL Venice

Trail Hog 5kTrail Hog 10kTrail Hog Half Marathon +1

From $30 Open

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Caloosa Fest

Sun, Dec 6 · Alva, FL Alva

5K Trail RunHalf Marathon

From $30 Open

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Ancient Oaks 100-Mile Endurance Run

Sat, Dec 19 · Titusville, FL Titusville

100-Mile Run

From $0 Closed

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Florida Outlaw Ultra

Sat, Jan 2 · Ocklawaha, FL Ocklawaha

13.1 Mile Trail Run6 Hour Trail Run12 Hour Trail Run +2

From $69 Open

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16th Annual Vista View 360 Ultramarathon & Relay

Sun, Jan 3 · Davie, FL Davie

Vista View 360 RelayVista View 360 Ultramarathon

From $75 Open

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Swamp Forest Trail Run

Sat, Jan 9 · Tallahassee, FL Tallahassee

Quarter MarathonHalf Marathon20-Mile Challenge

From $39 Closed

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OUTLAST ORLANDO

Sat, Jan 16 · Clermont, FL Clermont

6 Hour Challenge

From $90 Open Closing Soon

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Scrub Jay Races

Sat, Jan 23 · Oscar Scherer State Park, Osprey, FL Oscar Scherer State Park, Osprey

Virtual Scrub Jay 5KScrub Jay 5KVirtual Scrub Jay 10K +1

From $39 Open

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OUTLAST PALM BEACH

Sat, Jan 23 · West Palm Beach, FL West Palm Beach

6 Hour ChallengeOutlast ULTRA - 12 Hour ChallengeOutlast ULTRA - 24 Hour Challenge

From $90 Open

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OUTLAST TAMPA

Sat, Jan 30 · Lakeland, FL Lakeland

6 Hour Challenge

From $90 Open

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Gopherdillo Trail Run

Sat, Feb 6 · Bradenton, FL Bradenton

Gopherdillo 5kGopherdillo 10K

From $25 Open

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Picayune 10 Miler

Sat, Feb 13 · Naples, FL Naples

Legacy Runner (5x finishers ONLY!)10 Mile Trail Run

From $40 Open

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The Florida Run @ Manatee Springs State Park

Fri, Feb 19 · Chiefland, FL Chiefland

5K5K10K +5

From $36 Open Closing Soon 75 spots left

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Sasquatch

Sun, Feb 21 · Venice, FL Venice

5kVirtual race10k +1

From $30 Open

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The MILE

Sat, Mar 13 · Sarasota, FL Sarasota

The MILE Endurance

From $75 Open

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AdventHealth Silver Springs Half Marathon, 10K & 5K

Sat, Mar 27 · Silver Springs, FL Silver Springs

5K Trail Run5K Trail Run10K Trail Run +5

From $35 Open

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Dunedin 5K Kilted Trail Run

Sat, Apr 3 · Dunedin, FL Dunedin

Dunedin Highland Games 5K Kilted Trail Run & WalkDunedin Highland Games 5K Kilted Trail Run & Walk

From $35 Closed

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The Florida Run @ Colt Creek State Park

Sat, Apr 17 · Lakeland, FL Lakeland

5K5K10k +3

From $35 Open

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Withlacoochee Forest Trail Marathon

Sun, Apr 18 · Hernando, FL Hernando

10K10KHalf Marathon +3

From $40 Open

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Gator Wilderness Camp Trail Run/Walk 5k, 10k & 15k

Sat, Apr 24 · Punta Gorda, FL Punta Gorda

Kids Fun DashKids Fun DashGator Wilderness 5k +7

From $0 Closed

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Stomp Out Suicide Trail Race

Sat, May 15 · Dade City, FL Dade City

1 Mile Run/Walk1 Mile Fun Run/Walk5K Trail Run/Walk +3

From $15 Open 50 spots left

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The Florida Run LEFTOVER Trail Race

Sat, Jun 19 · Clermont, FL Clermont

4 Mile4 Mile8 Mile +1

From $20 Open

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