Trail Run races in Orlando, FL

Looking for trail races near you in Orlando, FL? There are 11 upcoming trail races listed here. The next one is Labor Day Triple on Sat, Sep 5, 2026 at 2529 Cady Way — see the full list below for dates, venues, and registration links, and browse trail races in other cities.

All 5K (171) 10K (65) Half Marathon (46) Marathon (12) Trail Run (11)

Sat, Sep 5, 2026 Labor Day Triple 2529 Cady Way · Winter Park, FL · From $30 5K10KHalf MarathonMarathonTrail Run Trail
Sat, Oct 24, 2026 PawPals Endeavor: Spoooky Edition 2026 and PawPals 4 Life 5k 31515 Wekiva River Road · Sorrento, FL · From $45 5KTrail Run Trail
Sat, Oct 31, 2026 Nightmare on the Clermont Trails 5K 938 Victory Way · Clermont, FL · From $35 5KTrail Run Trail
Sat, Nov 7, 2026 Turkey Trails- Orlando TBD · Orlando, FL · From $17 5K10KHalf MarathonTrail Run Trail
Sat, Dec 19, 2026 Ancient Oaks 100-Mile Endurance Run 444 Columbia Blvd · Titusville, FL Trail Run Trail
Sun, Dec 27, 2026 Holiday Five Cady Way Trail Head · Winter Park, FL · From $30 5K10KHalf MarathonMarathonTrail Run Trail
Sat, Feb 13, 2027 AdventHealth Lake Apopka Scenic Trail 30K Run, 8 Miler & 5K Magnolia Park · Apopka, FL · From $32 5KHalf MarathonTrail Run Trail
Thu, Feb 18, 2027 Florida Five Wekiwa Springs State Park, Apopka; Kit Land Nelson Park, Apopka; Chapin Station, Winter Garden; Sanlando Park, Altamonte Springs; & Cady Way Park, Winter Park. · From $30 5K10KHalf MarathonMarathonTrail Run Trail
Sat, Feb 20, 2027 MileBuilt 2-Day Bridge Challenge 2535 Cady Way · Winter Park, FL · From $35 5K10KHalf MarathonMarathonTrail Run Trail
Sat, May 1, 2027 Sunshine Double 2529 Cady Way · Winter Park, FL · From $30 5K10KHalf MarathonMarathonTrail Run Trail
Sat, Jun 26, 2027 Independence Double 2529 Cady Way · Winter Park, FL · From $30 5K10KHalf MarathonMarathonTrail Run Trail

New to the distance? Read trail vs. road racing, or set your target with the pace chart.

Quick answers

When is the next trail race in Orlando?

The next Trail Run in Orlando, FL is Labor Day Triple on Sat, Sep 5, 2026 at 2529 Cady Way.

How many trail races are coming up near me in Orlando?

There are currently 11 upcoming trail races listed in Orlando, FL, each with a date, venue, and direct registration link.

What's the cheapest Trail Run in Orlando?

The lowest listed entry right now is Turkey Trails- Orlando at from $17. Registration prices usually rise as race day nears, so early entry is cheapest.