Found 193 races near Windermere, FL

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JUL
27

Valrico, FL
• 27.1 miles
Tampa Bay HEAT Cross Country Fall 2026 Participating in Tampa Bay HEAT’s fall cross country season is convenient for families with kids of all grade levels, K through 12th grade. All High school,...
21
AUG
1

Winter Park, FL
• 14.4 miles
$30 -$65
Join us for the Inaugural Exclusive Endurance Mid-Distance Track Meet, hosted by Olympic Trials Marathoner and 5x Track Shack Series Champion Erica Weitz. This high-energy event is designed for...
3K 5K
24
AUG
8

Ocala, FL
• 38.6 miles
$35 -$39
5K trail with supporting local charities and post-race festivities
5K
74
AUG
8

Orlando, FL
• 24.2 miles
$30 -$45
Out-and-back 5K & 10K at Cypress Grove Park, Orlando, starting at 8:00 AM.
5K 10K
23
AUG
8

Wildwood, FL
• 26.7 miles
$12 -$15
Lace-up your XC spikes and get ready to show off your fitness at the Preseason Preview at the Sand Hill Scout Reservation. This course has been home to multiple district and regional cross...
2K 3K 5K
27
AUG
8

Orlando, FL
• 47.9 miles
$30 -$55
Join us for the Triple H 5k – Heart. Health. Hope., a community-centered run/walk designed to promote wellness, inspire hope, and bring people together.   ABOUT THE RACE Triple H 5K, Heart,...
5K
18
AUG
9

Clermont, FL
• 36.3 miles
$45 -$250
The 2026 AdventHealth Cool Sommer Mornings Triathlon-Duathlon-5K SeriesFour races. Four themes. Endless fun. Dive into a summer of adventure with the 2026 AdventHealth Cool Sommer Mornings Series...
5K
502
AUG
15

Ocala, FL
• 49.3 miles
$30
Join us for the 2026 Ocala Beer Mile!  A one-of-a-kind event that combines running, camaraderie, and liquid courage that stamps your passport to tomfoolery! The race will take place on Saturday,...
18
AUG
15

Plant City, FL
• 54.6 miles
$40 -$55
Scenic two-loop 5k through Keel Farms in Plant City, FL, paired with local craft beer.
5K
33
AUG
15

Brooksville, FL
• 29.9 miles
$25
Race day registration will begin at 6:30am and end at 7:30am.          Preregistered race  is $25 until race day. Race day price is $30.  Students are only $15. T-shirts are guaranteed to...
5K
23
AUG
16

Kissimmee, FL
• 36.3 miles
$40 -$55
A craft-beer-themed 5K at Formosa Winery in Kissimmee, FL, with a finisher medal and pint of beer.
5K
15
AUG
22

Lakeland, FL
• 46.6 miles
$25
Science-based 10k and half marathon training program with group support in Lakeland, FL.
19
AUG
22

Orlando, FL
• 5.7 miles
$35 -$40
We are excited to have you join us for our 4th Annual Pride of the Patriots 5K!  This year the race will be taking place at Bill Fredrick Park at Turkey Lake.  With over 200 participants, the...
5K
36
AUG
25

Orlando, FL
• 7.3 miles
$15 -$20
Join the AdventHealth University community for our 3K (1.86 miles) Walk/Run on August 25, 2026! Whether you are a seasoned runner aiming for a personal best or looking to enjoy a morning walk...
3K
28
AUG
25

Lakeland, FL
• 49.6 miles
The LRC Kids Run Club is a running club for children to prepare them for a lifetime of running. The program is held during the school year, is gender-neutral, and is designed for children in...
14
AUG
29

Ocala, FL
• 41.4 miles
$15
Ocala Kids Run – 1 Mile Fun Run at Baseline Greenway Think you're one of the fastest kids in Marion County? Prove it at the Ocala Kids Run, a FREE 1-mile chip-timed fun run happening Friday,...
1m
30
AUG
29

Viera, FL
• 52.2 miles
$35 -$40
Football-themed 2-mile race in Viera, FL with finisher medals and a tailgate party.
2m
14
SEP
5

Kissimmee, FL
• 37.4 miles
$30 -$60
Have you ever wanted to strip down and take a run in the buff? Come out and streak with us at the 13th annual clothing optional run at Cypress Cove Nudist Resort on Saturday  September 5th, 2026....
5K
18
SEP
5

Winter Park, FL
• 14.8 miles
$30 -$230
Running event out-and-back course in Winter Park
5K 10K Half Marathon Marathon 50K
133
SEP
5

Howey In The Hills, FL
• 15.3 miles
$45 -$50
Unique resort grounds 5K through lakes, golf fairways, gardens, and historic architecture
5K
44