Twilight Trail Trot 2026 — Ocala, FL

Date
May 27, 2026
Location
Ocala, FL
Venue
8924 US-441
Start Time
7:45 PM
Entry Fee
$20.00
Events
Trail Race
Includes
T-Shirt
Register NowRegistration Open
Join us for an unforgettable twilight trail running experience at the Santos trailhead on May 27th, brought to you by Radical Runs, Ocala Runners Club, and Santos Bike Shop! As a special collaboration with the Hump Day Hustle mountain bike race series, we're introducing the Twilight Trail Trot - a unique 2.8 ish-mile running race that will test your endurance and thrill your senses as you navigate the beautiful trails under the enchanting glow of twilight. Race Details: Date: May 28 Start Time: Twilight (exact time will be provided closer to race day) Location: Santos Bike Shop Distance: 2.8 miles (ish) Mandatory Gear: As this race takes place at twilight, all participants are required to wear a headlamp to ensure a safe and enjoyable experience for everyone. Race Swag: Commemorative race shirts will be available for purchase separately. Don't miss the chance to add this unique event to your collection of running memorabilia! To participate in this one-of-a-kind race, simply sign up on

Hotels Near This Race

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Twilight Trail Trot 2026 — Ocala, FL

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Race Travel Insurance

Don't forget travel insurance for May 27.

You've trained for months and booked a trip to Ocala, FL. A pre-race injury, a delayed flight, or a family emergency can derail the whole thing. Travel insurance can help cover your race entry fee, hotel, and flights if you can't make it, and may cover medical costs if something goes wrong on the course. Plans typically only run 5-7% of your total trip cost — and running events are covered under standard plans with no additional coverage needed.

  • Trip cancellation up to 100% of prepaid costs
  • Running events covered under standard plans — no add-ons needed
  • Trip interruption up to 150% of non-refundable costs
  • Emergency medical up to $250,000
  • Cancel For Any Reason add-on available
  • 24/7 real-time support

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