Middleburg
Trail Running Calendar near Middleburg 2026-2027
Explore the top trail runs near Middleburg 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
A free scavenger hunt run from 1st Place Sports San Marco with New Balance shoe demos, teams of 4 to 5, photo clue stops, post-run breakfast and prizes.
October 2026
Trail and ruck events of 5 and 10 miles at Jennings State Forest on October 18, 2026, featuring the Sawyer Trail, Many Seeps Bridge, cupless aid station, and awards.
An off road Halloween 5K at Waldo MX with obstacles, infected zones, and flag football style life flags to protect; open to ages 8 and up.
December 2026
Experience the longest trail race in Northeast Florida with distances from 7 to 100 miles on a scenic 7.2 mile forested loop in Middleburg.
5K run and walk at Congaree and Penn farm in Jacksonville on December 5, 2026, for participants 21+ with chip timing, included race items, and farm passes available on site.
January 2027
Experience the diverse terrain of Florida’s Pioneer Trail with a 50k, marathon, 12k, or 7k race featuring technical sections, stream crossings, and scenic ravine vistas.
February 2027
Experience the Sombrero Ultra Running Festival in Florida, featuring timed events ranging from 3 to 48 hours for individual runners and relay teams on a supported loop course.
Trail 25K and 50K in Bryceville, FL on February 20, 2027 with forest roads, supported aid stations, eight-hour cutoffs, race shirts, awards and youth program proceeds.
Jacksonville Spartan Event Weekend Feb 27 28 2027 at Diamond D Ranch features Sprint and Super obstacle races, kids events, a four hour Hurricane Heat, and spectator access.
Gator Dash Trail Run at Diamond D Ranch near Jacksonville offers scenic Trail 10K and half marathon courses with mostly non technical but occasionally muddy and tricky terrain.
April 2027
A 5K mud run with 26 obstacles through woods, fields and ponds, plus a 1-mile fun run, held in Green Cove Springs to benefit Seamark Ranch.
May 2027
A family friendly mud run on May 1, 2027 at Jacksonville Equestrian Center featuring a roughly 5 km obstacle course, mud pits, a pre-party, and registration options including a VIP package.