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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 11 exciting trail runs in the area. Check out our detailed list below to find your next local trail run.

October 2026
A weekend of obstacle-course events at Lake Nona with Sprint, Super, kids races, Hurricane Heat and a pre-event workshop, Oct 9 to 11, 2026.
December 2026
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
A beachside 5K color fun run in downtown Cocoa Beach on January 2, 2027, raising funds for Cocoa Beach Main Street with a northbound out-and-back course to Lori Wilson Park.
Point to point 50 mile trail event in DeBary, FL with 50K and 17K options, five aid stations, and a finish at Central 28 Beer Company.
A two day out and back on the Spring-to-Spring Trail at Gemini Springs Park offering 5K to 50K distances with cupless aid and a manual finish clock.
Multiple distance trail event in Christmas, Florida on January 30 and 31, 2027, featuring rarely traveled single track through several state forests and notable birdlife.
February 2027
An ultramarathon on Florida’s Space Coast offering multiple distances on February 20, 2027, limited to 100 runners with a beach finish and a 31-hour cutoff.
March 2027
A chip timed 5K at Formosa Winery in Kissimmee FL on March 14 2027 with wine tasting, cider, a finisher medal and results by J3 Timing.
May 2027
A point to point 5K in Winter Park finishing on a tree canopied dirt road; in person finishers receive a young tree and a T shirt, with a free kids run and virtual option.
Beach running championships in Cocoa Beach on May 30, 2027, with 5K, 10K and 15K options, barefoot and walker divisions, medals for finishers and a beach awards party.
June 2027
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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