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

Twilight Trail Trot takes place at 8924 US-441 in Ocala, Florida on May 27, 2026. The event features a 5-mile run starting at 7:45 PM, making it an evening race option for runners in the area. Entry is affordable at $20.00, making it accessible for athletes looking for a local running event. The evening start time means you'll be racing as daylight fades, so plan your travel and accommodation accordingly if you're coming from out of town. Ocala's location in central Florida provides easy access via major highways for regional participants.

From the Race Organizer
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

Find accommodation close to the start line in Ocala, FL. Sorted by distance from the race venue. Book early — race weekend hotels fill fast.

RaceHotelFinder earns a small commission when you book through links on this page, at no extra cost to you. Results are sorted by distance from the race venue.

Twilight Trail Trot 2026 — Ocala, FL

Race day is approaching. Hotels fill up fast.

--Days
:
--Hours
:
--Mins
:
--Secs
Book a hotel for race weekend

Race weekend dates pre-loaded on Booking.com. RaceHotelFinder may earn a commission at no extra cost to you.

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
Get a Quote — Faye Travel Insurance

Affiliate links — we may earn a commission at no cost to you. Coverage terms vary by state and plan. Review policy details before purchase.

More Races

Browse all upcoming races in Florida →

Other upcoming races in Florida

Run Unlimited Sprint 2026 — Saint Petersburg, FLSaint Petersburg, FLJul 31, 2026From $$25.00
Find Hotels →
BHI 2nd Annual 5K & Fun Run 2026 — Jacksonville, FLJacksonville, FLAug 1, 2026From $$15.00
Find Hotels →
Bushwacker 5K 2026 — Pensacola Beach, FLPensacola Beach, FLAug 1, 2026From $$35.00
Find Hotels →
Move for Hope – Wings & Sunshine – 1K • 5K • 10K • Half Marathon Virtual Races 2026 — Miami, FLMiami, FLAug 1, 2026From $$60.00
Find Hotels →

Frequently Asked Questions

When is Twilight Trail Trot 2026 — Ocala, FL?

Twilight Trail Trot 2026 — Ocala, FL takes place on May 27, 2026. The race is held in Ocala, Florida.

Where is Twilight Trail Trot 2026 — Ocala, FL held?

Twilight Trail Trot 2026 — Ocala, FL is held at 8924 US-441 in Ocala, Florida.

Where can I find hotels near Twilight Trail Trot 2026 — Ocala, FL?

RaceHotelFinder shows hotels sorted by distance from the race venue in Ocala. Use the map or list view on this page to compare options and book race weekend accommodation.