Upcoming Races Near Osprey, FL - Matching: Trail Races

Name: Run Manatee - Rye Preserve 5K -2026
Start: 2026-11-21
End: 2026-11-21
Location: Parrish

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Haunted 5K & 10K at Ann and Chuck Dever Regiona...

Englewood, FL

Saturday, October 11th, 2025

10K

Trail

View details for race Haunted 5K & 10K at Ann and Chuck Dever Regional Park, Eanglewood, FL (41) 50

Trick or Trot 5K - Presented by Mazda of Port C...

Englewood, FL

Saturday, October 18th, 2025

1 Mile

Trail

View details for race Trick or Trot 5K - Presented by Mazda of Port Charlotte

Run The Point

Palmetto, FL

Saturday, October 25th, 2025

Trail

Fast

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Gopher Weedon Trail Run

Saint Petersburg, FL

Saturday, October 25th, 2025

Trail

View details for race Gopher Weedon Trail Run

Pie Gobbler 5K & 10K at Ann and Chuck Dever Reg...

Englewood, FL

Saturday, November 15th, 2025

10K

Trail

View details for race Pie Gobbler 5K & 10K at Ann and Chuck Dever Regional Park, Eanglewood, FL (46) 50

Run Manatee - Rye Preserve 5K

Parrish, FL

Saturday, November 22nd, 2025

Trail

View details for race Run Manatee - Rye Preserve 5K

Fusion Fest 5k

North Port, FL

Saturday, November 22nd, 2025

1 Mile

Trail

View details for race Fusion Fest 5k

Chase the Dreidel 5K

Saint Petersburg, FL

Sunday, December 7th, 2025

Trail

View details for race Chase the Dreidel 5K

Santa Run

Sarasota, FL

Sunday, December 14th, 2025

1 Mile

Trail

View details for race Santa Run

Holiday 5K & 10K at Ann and Chuck Dever Regiona...

Englewood, FL

Saturday, December 20th, 2025

10K

Trail

View details for race Holiday 5K & 10K at Ann and Chuck Dever Regional Park, Eanglewood, FL (51) 50

San Pedro 5k Resolution Run!

North Port, FL

Saturday, January 3rd, 2026

1 Mile

Trail

View details for race San Pedro 5k Resolution Run!

Sarasota Half Marathon

Sarasota, FL

Saturday, January 10th, 2026

Half

10K

Trail

View details for race Sarasota Half Marathon

Medal Madness 5K & 10K at Ann and Chuck Dever R...

Englewood, FL

Saturday, January 17th, 2026

10K

Trail

View details for race Medal Madness 5K & 10K at Ann and Chuck Dever Regional Park, Eanglewood, FL (03) 50

Scrub Jay Races

Osprey, FL

Saturday, January 24th, 2026

10K

Trail

View details for race Scrub Jay Races

Pine Island Calusa Trail 5K Run and Walk - 2025

Bokeelia, FL

Saturday, January 31st, 2026

Trail

View details for race Pine Island Calusa Trail 5K Run and Walk - 2025

Mardi Gras Canicross, 10k and 5k Run

Sarasota, FL

Sunday, February 1st, 2026

10K

1 Mile

Trail

View details for race Mardi Gras Canicross, 10k and 5k Run

Gopherdillo Trail Run

Bradenton, FL

Saturday, February 7th, 2026

10K

Trail

View details for race Gopherdillo Trail Run

St. Petersburg Distance Classic

Saint Petersburg, FL

Sunday, February 8th, 2026

Marathon

Half

10K

Trail

View details for race St. Petersburg Distance Classic

8th Annual - Venice Half Marathon & 5k | ELITE ...

Venice, FL

Saturday, February 14th, 2026

Half

Trail

View details for race 8th Annual - Venice Half Marathon & 5k | ELITE EVENTS

Love on the Run 5K

Punta Gorda, FL

Saturday, February 14th, 2026

Trail

View details for race Love on the Run 5K

Sasquatch

Venice, FL

Sunday, February 15th, 2026

15K

10K

Trail

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Viking 5K & 10K at Ann and Chuck Dever Regional...

Englewood, FL

Saturday, February 21st, 2026

10K

Trail

View details for race Viking 5K & 10K at Ann and Chuck Dever Regional Park, Eanglewood, FL (08) 50

Shoot for the Stars 5k

Venice, FL

Saturday, February 28th, 2026

Trail

View details for race Shoot for the Stars 5k

Medal Madness 5K & 10K at Ann and Chuck Dever R...

Englewood, FL

Saturday, March 21st, 2026

10K

Trail

View details for race Medal Madness 5K & 10K at Ann and Chuck Dever Regional Park, Eanglewood, FL (12) 50

RUN Manatee - Tom Bennett Park 5K - 2026

Bradenton, FL

Saturday, April 11th, 2026

Trail

View details for race RUN Manatee - Tom Bennett Park 5K - 2026

Pirate 5K & 10K at Ann and Chuck Dever Regional...

Englewood, FL

Saturday, April 18th, 2026

10K

Trail

View details for race Pirate 5K & 10K at Ann and Chuck Dever Regional Park, Eanglewood, FL (16) 50

Gator Wilderness Camp Trail Run/Walk 5k, 10k & 15k

Punta Gorda, FL

Saturday, April 25th, 2026

10K

15K

Trail

View details for race Gator Wilderness Camp Trail Run/Walk 5k, 10k & 15k

Luau 5K & 10K at Ann and Chuck Dever Regional P...

Englewood, FL

Saturday, May 16th, 2026

10K

Trail

View details for race Luau 5K & 10K at Ann and Chuck Dever Regional Park, Eanglewood, FL (20) 50

Medal Madness 5K & 10K at Ann and Chuck Dever R...

Englewood, FL

Saturday, June 20th, 2026

10K

Trail

View details for race Medal Madness 5K & 10K at Ann and Chuck Dever Regional Park, Eanglewood, FL (25) 50

Run Manatee - Coquina Beach 5K - 2026

Bradenton Beach, FL

Saturday, July 11th, 2026

Trail

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

Run Manatee - Rye Preserve 5K -2026

Parrish, FL

Saturday, November 21st, 2026

Trail

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

Explore more in Osprey, FL

Distances:

5K 10K Half Marathon Marathon

Months:

August September October

Tags:

Trail Boston Qualifiers Fast Courses

State:

All Florida races

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