Upcoming Races in Oldsmar, FL 2026-2027

6th Annual Summer Heat 5K Run/Walk

Thonotosassa, FL

Saturday, June 6th, 2026

Featured

5K

Trail

View details for race 6th Annual Summer Heat 5K Run/Walk

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BIGFOOT CHALLENGE 5k Flag Day Run/Walk

Tampa, FL

Sunday, June 14th, 2026

5K

1 Mile

Trail

View details for race BIGFOOT CHALLENGE 5k Flag Day Run/Walk

The Best Bling Selection Of The Year 5K At HOB ...

Dunedin, FL

Sunday, June 14th, 2026

5K

Trail

View details for race The Best Bling Selection Of The Year 5K At HOB Brewing Company In Downtown Dunedin Florida

Best Bling Of The Year Summer 5K At HOB Brewing...

Dunedin, FL

Sunday, June 14th, 2026

5K

10K

Trail

View details for race Best Bling Of The Year Summer 5K At HOB Brewing Co Dunedin

Run Manatee - Coquina Beach 5K - 2026

Bradenton Beach, FL

Saturday, July 11th, 2026

5K

Trail

View details for race Run Manatee - Coquina Beach 5K - 2026

THe Dunedin Dog n' Suds Summer 5K At HOB Brewin...

Dunedin, FL

Saturday, August 22nd, 2026

5K

Trail

View details for race THe Dunedin Dog n' Suds Summer 5K At HOB Brewing Company In Downtown Dunedin

The Dunedin Oktoberfest 5K 10K at HOB Dunedin B...

Dunedin, FL

Saturday, September 26th, 2026

10K

5K

Trail

View details for race The Dunedin Oktoberfest 5K 10K at HOB Dunedin Brewing Company

The Dunedin Oktoberfest 5K 10K at HOB Brewing C...

Dunedin, FL

Saturday, September 26th, 2026

5K

10K

Trail

View details for race The Dunedin Oktoberfest 5K 10K at HOB Brewing Company Downtown Dunedin

Run The Point

Palmetto, FL

Saturday, October 3rd, 2026

5K

1 Mile

Trail

View details for race Run The Point

Chasing the Sun Endurance Run

Bradenton, FL

Saturday, October 10th, 2026

Half

Marathon

1 Mile

Trail

View details for race Chasing the Sun Endurance Run

Camo & Cobwebs 5K & 1 Mile Fun Run/Walk

Palm Harbor, FL

Saturday, October 17th, 2026

5K

1 Mile

Trail

View details for race Camo & Cobwebs 5K & 1 Mile Fun Run/Walk

A Kitten Place Black Cat 5K Fun Run

Valrico, FL

Saturday, October 24th, 2026

5K

Trail

View details for race A Kitten Place Black Cat 5K Fun Run

Gopher Weedon Trail Run

Saint Petersburg, FL

Saturday, October 24th, 2026

Trail

View details for race Gopher Weedon Trail Run

Dunedin Halloween Costume 5K 10 At HOB Brewing ...

Dunedin, FL

Monday, October 26th, 2026

5K

10K

Trail

View details for race Dunedin Halloween Costume 5K 10 At HOB Brewing Company 2 Story Beer Pavilion

Dunedin Veterans Day 5K 10K and Kids HONOR Dash...

Dunedin, FL

Sunday, November 8th, 2026

5K

10K

Trail

View details for race Dunedin Veterans Day 5K 10K and Kids HONOR Dash Celebrating All USA Veterans

The Dunedin Veterans Day 5K 10K and Kids Dash H...

Dunedin, FL

Sunday, November 8th, 2026

10K

5K

Trail

View details for race The Dunedin Veterans Day 5K 10K and Kids Dash Honor Runs

6th Annual Veterans Run

Tampa, FL

Saturday, November 14th, 2026

5K

10K

Half

Trail

View details for race 6th Annual Veterans Run

The Sand Hill Adventure Run

Brooksville, FL

Saturday, November 21st, 2026

5K

Trail

View details for race The Sand Hill Adventure Run

Run Manatee - Rye Preserve 5K -2026

Parrish, FL

Saturday, November 21st, 2026

5K

Trail

View details for race Run Manatee - Rye Preserve 5K -2026

Turkey Day 5K Tampa Bay

Tampa, FL

Thursday, November 26th, 2026

5K

Trail

Fast

View details for race Turkey Day 5K Tampa Bay

Your Next Step is the Cure

Plant City, FL

Saturday, December 5th, 2026

5K

Trail

View details for race Your Next Step is the Cure

Chase the Dreidel 5K

Saint Petersburg, FL

Sunday, December 13th, 2026

5K

Trail

View details for race Chase the Dreidel 5K

Downtown Dunedin Holiday 5K 10K and 15K With To...

Dunedin, FL

Saturday, December 19th, 2026

5K

10K

15K

Trail

View details for race Downtown Dunedin Holiday 5K 10K and 15K With Toy Drive

The Dunedin Holiday 5K 10K 15K At HOB Brewing C...

Dunedin, FL

Saturday, December 19th, 2026

5K

10K

15K

Trail

View details for race The Dunedin Holiday 5K 10K 15K At HOB Brewing Company In Downtown With Annual Toy Drive

Dunedin Holiday 5K 10K 15K with Holiday Toy Dri...

Dunedin, FL

Saturday, December 19th, 2026

5K

10K

15K

Trail

View details for race Dunedin Holiday 5K 10K 15K with Holiday Toy Drive At HOB Brewing Company Downtown Dunedin

2027 All Day Running Co. Clearwater Marathon & ...

Clearwater, FL

Saturday, January 30th, 2027

Half

5K

Marathon

Trail

View details for race 2027 All Day Running Co. Clearwater Marathon & Running Festival

Gopherdillo Trail Run

Bradenton, FL

Saturday, February 6th, 2027

5K

10K

Trail

View details for race Gopherdillo Trail Run

The Hunt for Sasquatch

Mulberry, FL

Saturday, February 6th, 2027

10K

5K

1 Mile

Trail

View details for race The Hunt for Sasquatch

Brighter Days 5K/Walk For Autism

Tarpon Springs, FL

Sunday, March 14th, 2027

5K

1 Mile

Trail

View details for race Brighter Days 5K/Walk For Autism

Upcoming Races Near Oldsmar, FL - Matching: Trail Races