Holiday
Trail Running Calendar near Holiday 2026-2027
Explore the top trail runs near Holiday for 2026-2027! We've gathered 20 exciting trail runs in the area. Check out our detailed list below to find your next local trail run.
September 2026
A community 5K/10K/15K on the Pinellas Trail in downtown Dunedin at HOB Brewing Company on September 27, 2026, with electronic timing, finisher medals and a post-race party including one free draft beer for participants 21 and over. The event support..
October 2026
A timed tower climb at Tampa City Center to the 41st floor with 861 steps, bailout floors, water stations, event t shirt, finisher medal, and awards across categories.
A Halloween-themed 5K, 1-Mile Fun Run and virtual 5K in Dunedin/Palm Harbor benefiting Club-214 Land & Sea and veteran support services.
The 14th Annual Gopher Weedon 8K Trail Run on October 24, 2026 follows 8 kilometers of dirt and boardwalk trails through Weedon Island Preserve, with professional timing, refreshments and proceeds benefiting Friends of Weedon Island.
November 2026
PHSC hosts a flat 5K and a 1 Mile run/walk on November 1, 2026 at PHSC West Campus with awards, participant shirts, and post-race refreshments.
A self-guided, point-to-point urban endurance tour of about 100 miles from Ybor City through Tampa Bay beaches to a finish at Coffee Pot Park in St. Petersburg.
A Brooksville race day on November 21, 2026 with a 5K trail run, a 2.5K costume turkey trot, and a 0.8K color run supporting local Scouting programs.
Thanksgiving morning 5K on the paved Upper Tampa Bay Trail in Tampa with costumes encouraged, finisher medals, music, and family-friendly activities.
Third annual Salty Soul Splash Dash is a 5K fun run in Dunedin on 11/28/2026 along the Pinellas Trail with race timing, a shirt, and a cold beverage.
December 2026
January 2027
A chip timed 5 km run and walk at Masaryk Winery in Masaryktown, Florida on January 16, 2027, with a helper registration option, race items including a t-shirt and wine glass, and results posted online by J3 Timing.
February 2027
Experience the world’s only indoor backyard ultra on treadmills where runners must complete 5 miles every hour to stay in the race until only one remains.
March 2027
Beachside event on March 6, 2027 offering a chip-timed 5K, a family 1-mile run/walk, and a virtual 5K with proceeds supporting Rotary projects.
April 2027
A 5K kilted trail run and walk in Dunedin with race shirt, medal, and festival admission included as part of the Highland Games.
May 2027
A stadium-based Spartan Stadion 5K at Raymond James Stadium with 20 obstacles, a kids race, and spectator access on May 1, 2027.
September 2027
An ultramarathon covering just over 46 miles along the Pinellas Trail between St. Petersburg, Tarpon Springs and Dunedin.