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Trail Running Calendar near Christmas 2026-2027

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Explore the top trail runs near Christmas for 2026-2027! We've gathered 12 exciting trail runs in the area. Check out our detailed list below to find your next local trail run.

September 2026
Sep
27
Su

Bodies Race Company - Orlando

Trail Run 3 mi 6 mi 13 mi
A race day at Jay Blanchard Park on 09/27/2026 with distances from a 50 m kid's dash to a 13.1 mile half marathon, chip timing for main races, event shirts and medals, plus volunteer and virtual options.
October 2026
Oct
10-11
Sa - Su

Orlando Spartan Weekend

Obstacle Run 5 km 10 km
Orlando Spartan Weekend at Lake Nona features sprint and super obstacle races, kids events, a Hurricane Heat and an obstacle workshop across Oct 9 to 11, 2026.
Oct
10
Sa

We Care 5K

Trail Run 5 km
Lutheran Counseling Services holds the We Care 5K on October 10, 2026 in Longwood to raise funds and awareness for mental health. The event offers an in person 5K along parts of the Seminole Trail and a virtual 5K option.
November 2026
Nov
7
Sa

Bodies Race Company - Orlando

Trail Run 3 mi 6 mi 13 mi
Celebrate Thanksgiving with a series of themed races including a Half Marathon, 10k, and 5k in Orlando. Enjoy chip timed results, finisher medals, and family friendly distances like the Kids Dash and 1 Mile fun run.
December 2026
Dec
13
Su

Bodies Race Company - Orlando

Trail Run 3 mi 6 mi 7 mi
Candy Cane Course in Orlando on 12/13/2026 offers 5K, 10K, 15K, a 1 Mile, a Kids Dash and a virtual option. Entries normally include a designer shirt, custom bib and finisher medal, with youth pricing for ages 12 and under.
Dec
19-20
Sa - Su

Ancient Oaks 100-Mile Endurance Run

Trail Run 100 mi
Invitation only no fee 100 mile endurance run in Enchanted Forest Nature Sanctuary, Titusville FL with 29 loops of a 3.46 mile trail and a 60 runner cap.
January 2027
Jan
23
Sa

Monroe Cross Trail 50 Mile Ultra

Trail Run 17 km 50 km 50 mi
Point to point trail ultramarathon in DeBary, Florida with 50 mile, 50K, and 17K options, aid stations, and a finish at Central 28 Beer Company.
Jan
30-31
Sa - Su

Forgotten Florida

Trail Run Walk 8 mi 15 mi 50 mi 100 mi
A multi-distance trail event in Christmas, Florida on January 30 and 31, 2027, running through Tosohatchee and nearby state forests with single track, varied terrain, wildlife viewing, course maps, aid station details, and crew and volunteer support.
February 2027
Feb
20
Sa

Space Pirate 100

Trail Run 33 mi 50 mi 100 mi
Multi-distance ultramarathon along Florida's Space Coast and Treasure Coast, limited to 100 runners and requiring support crew.
March 2027
Mar
14
Su

Formosa Spiked Apple 5K

Trail Run Walk 5 km
A chip timed 5K run/walk at Formosa Winery in Kissimmee on March 14, 2027. Registration includes a T-shirt, a medal that doubles as a bottle opener, a pour of cider and a homemade cider donut.
May 2027
May
8
Sa

Run for the Trees Jeannette Genius McKean Memorial 5K

Road Race Trail Run Walk 5 km
A point to point 5K in Winter Park with a final mile on a tree canopied dirt road, event swag, reusable-cup hydration options, and a tree sapling for in-person finishers.
June 2027
Jun
26-27
Sa - Su

Independence Double

Urban Trail 5 km 10 km ... 26 mi 50 km
Two-day running event on June 26 and June 27, 2027 at Cady Way Trail Head in Winter Park, FL. Distances range from 5K to 50K on flat, looped paved trails with a pavilion aid station and hand timing.
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