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Trail Running Calendar near Holiday 2026-2027

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Explore the top trail runs near Holiday for 2026-2027! We've gathered 19 exciting trail runs in the area. Check out our detailed list below to find your next local trail run.

September 2026
Sep
5
Sa

Pinellas Trail Challenge

Trail Run 46 mi
A 46 mile ultramarathon on the Pinellas Trail from St. Petersburg to Tarpon Springs and returning to Dunedin on September 5, 2026.
Sep
26
Sa

Bodies Race Company - Tampa

Trail Run 3 mi 6 mi 13 mi
A multi distance running event in Tampa with a half marathon, 10K, 5K, 1 mile, kids dash and virtual option. Features include chip timing, designer shirts and finisher medals, with youth pricing for ages 12 and under.
Sep
27
Su

Dunedin Okotbeerfest 10k

Trail Run Walk 5 km 10 km 15 km
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
Oct
3
Sa

Tunnel to Towers Climb - Tampa

Urban Trail
A timed climb of 861 steps to the rooftop of Tampa City Center with official timing to the 39th floor, bailout floors, water stations and on site medics.
Oct
17
Sa

Camo & Cobwebs 5K

Trail Run Walk 5 km
Camo & Cobwebs 5K and 1 Mile Fun Run/Walk on the Pinellas Trail in Dunedin, Florida supports Club-214 Land & Sea. The event features a timed 5K with awards, a family-friendly 1 Mile, a costume contest, and proceeds for veteran services.
Oct
24
Sa

Gopher Weedon Trail Run

Trail Run 8 km
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
Nov
8
Su

Dunedin Veterans Day 10K Runs

Trail Run Walk 5 km 10 km
A Veterans Day running event in Dunedin offering a 5K, a two-loop 10K and a kids Honor Dash on the paved, stroller friendly Pinellas Trail with American themed finisher medals and timed results.
Nov
8
Su

Bodies Race Company - Tampa

Trail Run 3 mi 6 mi 13 mi
Celebrate Thanksgiving with this family friendly event in Tampa featuring distances from a Kids Dash to a Half Marathon. Enjoy chip timed results, finisher medals, and festive treats at the finish line.
Nov
14
Sa

Veterans Run - Tampa

Trail Run 5 km 10 km 13 mi 16 mi
The 6th Annual Veterans Run in Tampa returns with in-person and virtual races along the Courtney Campbell Causeway, offering 5K, 10K, half marathon, and a 15.5 mile course with certified timing and aid stations.
Nov
14-15
Sa - Su

Tampa Bay 100

Trail Run 100 mi
A point-to-point urban endurance tour from Ybor City to St. Petersburg covering about 100 mile of Tampa Bay sights, beaches and waterfronts. The mostly flat route includes five aid stations, supplies caches and specific pacing and mandatory gear rule..
Nov
21
Sa

The Sand Hill Adventure Run

Trail Run 3 km 5 km
A set of runs on November 21, 2026 in Brooksville, Florida features a 5K trail run, a 2.5K Turkey Trot with costumes encouraged, and a short Color Fun Run with colored powder. Proceeds support Scouting programs.
Nov
26
Th

Turkey Day 5K Tampa Bay

Trail Run 5 km
A Thanksgiving 5K on the Upper Tampa Bay Trail in Tampa, FL on November 26, 2026. The chipped timed 5K includes a finisher medal, a soft short sleeve shirt, age group awards, free photos, and holiday-themed elements.
Nov
28
Sa

Salty Soul Splash Dash

Trail Run 5 km
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
Dec
12
Sa

RunFluent Christmas

Trail Run 4 mi 13 mi
Trail event in Lutz FL on December 12 2026 offering a new half marathon, relay options, a 4 miler, and a youth 4 mile.
Dec
19
Sa

Downtown Dunedin Holiday 15K with Toy Drive

Trail Run Walk 5 km 10 km 15 km
A holiday run in downtown Dunedin on December 19, 2026 featuring 5K 10K and 15K routes on the Pinellas Trail with electronic timing finisher medals shirts and a post race beer option for those 21 and over.
Dec
27
Su

Bodies Race Company - Tampa

Trail Run 3 mi 6 mi 9 mi
Holiday-themed races at Gadsden Park in Tampa on December 27, 2026, with distances from a kids 50 m dash to 15K, plus a virtual option, chip-timing, shirts, medals, photos, and finish-line treats.
January 2027
Jan
16
Sa

Masaryk Wine Run 5k

Trail Run 5 km
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.
April 2027
Apr
10
Sa

Turtle Trot 10K

Trail Run Walk 5 km 10 km
Turtle Trot is a 5K run and walk at SunWest Park in Hudson, Florida, with a paved course around old salt mines. Proceeds support Pasco County's PAIR program and every registered participant receives a finisher award.
May 2027
May
1
Sa

Raymond James Stadium Spartan Stadion 5K

Obstacle Run 5 km
A Stadion 5K obstacle race at Raymond James Stadium on May 1, 2027, featuring 20 obstacles, stair sections, a kids race, and spectator options.
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