Events in Winter Garden, Florida | 2026-2027

Dream Finders Homes Hippity Hop 5K [floridarunningco.com] [Register at runsignup.com]
Sat, Apr 04, 2026 at 8:00 AM
Description
When: Saturday, April 4, 2026

Start/Finish: Winter Garden/Windermere/Clermont Area

Race Day Schedule:
- 8:00am - 5K start
9:15am - Kids Races start

Hippity Hop 5K includes:
- All 5K participants will...
When: Saturday, April 4, 2026

Start/Finish: Winter Garden/Windermere/Clermont Area

Race Day Schedule:
- 8:00am - 5K start
9:15am - Kids Races start

Hippity Hop 5K includes:
- All 5K participants will receive a chip timed race, t-shirt, and finishers medal.
- FREE Coffee and Ice Cream from Foxtail Coffee and Kelly's Ice Cream in Winter Garden/Clermont
- All Kid race participants will receive a race medal and bib.
Distances vary between 50 yard to 200 yard dashes depending on the age and ability of your child.

For additional race day details, please go to https://www.floridarunningco.com/hippity-hop-5k
5k Run
Winter Garden, Florida, 34787, United States
OpenStreetMap Google Maps

Hickory Hammock 5K & Kids Fun Run [runsignup.com]
Sun, Sep 27, 2026 at 7:30 AM

Description

THE HICKORY HAMMOCK 5K & KIDS FUN RUN IS NO LONGER BEING OFFERED AT THIS TIME

***Please note - this race is only for members of the gated community Hickory Hammock at Johns Lake and their friends &...

THE HICKORY HAMMOCK 5K & KIDS FUN RUN IS NO LONGER BEING OFFERED AT THIS TIME

Please note - this race is only for members of the gated community Hickory Hammock at Johns Lake and their friends & family

Join us for the10th annual Hickory Hammock 5K and Kids Fun Run event on Sunday, September 28th. Enjoy a 3.1 mile run/walk through our beautiful neighborhood starting and ending at the community park. For the kids, a short fun run will be held after the race. Participants and spectators can enjoy breakfast food and drinks after the races. Whether running, walking, cheering or just coming for the food...we hope you all can make it!

All proceeds from this race go to Edgewood Children's Ranch - learn more at https://edgewoodranch.com/

3.1 Miles 5k Fun Run Kids Run Walk
Winter Garden, Florida, 34787, United States
OpenStreetMap Google Maps
Turkey Trails- Orlando [runsignup.com]
Sat, Nov 07, 2026 at 8:00 AM
Description
Join us for the annual Turkey Trails 5k/10k/Half Marathon! A fun, Thanksgiving-themed event that is perfect for the whole family.

The fun includes -
- Great Swag - designer shirt & custom medal
*...
Join us for the annual Turkey Trails 5k/10k/Half Marathon! A fun, Thanksgiving-themed event that is perfect for the whole family.

The fun includes -
- Great Swag - designer shirt & custom medal
- Chip-timing with live results and awards
- Free photos
- Delicious Treats waiting at the finish line
- Plenty of fun!
Grab your friends and family, you are not going to want to miss this one!

Can't make the race? No problem! We offer a virtual race option where you can run anywhere, at any time, and still earn the fun swag!

*Youth-based pricing for the 5k/10k, 12 & Under are only $17!
- Half Marathon registration includes a custom bib, designer shirt, and an awesome finisher medal!
- 5k/10k registration includes a custom bib, designer shirt, and an awesome finisher medal!
- 1 Mile registration is untimed and includes a custom bib, designer shirt, and an awesome finisher medal!
- The kid's dash is a fun, untimed dash for our kiddos ages 10 and under. Registration includes a mini bib, youth-sized shirt, and a specifically crafted medal for our kids' dash event! (If your child wants to run the kid's dash, and doesn't want the SWAG, they are welcome to run with us on race day for free!)
*Register by midnight on Thursday, two Thursdays before race day, to guarantee your shirt!
1 Miles 3.1 Miles 6.2 Miles 13.1 Miles Run Trail Virtual
TBD, Winter Garden, Florida, 34711, United States
OpenStreetMap Google Maps
WGPAL Donut Dash 5K [runsignup.com]
Sat, Nov 07, 2026 at 8:00 AM

Description

This year's Donut Dash 5K will take place in beautiful and historic Downtown Winter Garden. Run or walk through the timeless neighborhoods and down by Lake Apopka!

OK, so where else can you not feel...

This year's Donut Dash 5K will take place in beautiful and historic Downtown Winter Garden. Run or walk through the timeless neighborhoods and down by Lake Apopka!

OK, so where else can you not feel guilty about eating as many donuts as you want!?!!

Join us for this great event and support the Winter Garden Police Athletic League. The Police Athletic League provides a free 8 week summer camp for 140 underprivileged and at-risk kids. Additionally the PAL provides a Holiday Gift’s for Kids Program which supplies holiday gifts and meal vouchers to approximately 400 local in-need children who would most likely go without during the holiday season.

EAT DONUTS, RUN, EAT DONUTS, HAVE FUN!!!

Here is how it works...You can run this just like a regular 5k or you can...

EAT DONUTS!!!

Every donut eaten in one of the three “donut zones” will take 30 seconds off of your final run time. Example; eat 4 donuts and a total of 2 minutes will be taken off of your final run time. Anyone who eats 12 or more donuts will receive an additional bonus of 1 minute per donut (over 12) taken off their final run time.

“Donut zones” will be located at the 1 mile mark, 2 mile mark, and 3 mile mark of the course. All donuts must be finished in the “donut zones”.

Each adult entry comes with 1 free child’s entry into the kid’s fun-run (if you have more than 1 child they can take part also at no additional cost, after all it is just plain fun).

LIVE MUSIC, and Sponsor tents!!

All registered participants will receive a race medal. All finishers as listed below will receive an additional medal:

Medals will be provided to first and second place finishers (male and female) in all age categories. And 1st, 2nd, 3rd place male and female overall.

BEST DONUT COSTUME PRIZE!!

RACE DAY REGISTRATION available (unless sold out

Online registration is open until Friday, November 6th 11:59pm. Anyone registering after 12pm (noon) on Friday, 11/06/26, will be required to pick up their packet on Saturday morning, race day. Race day registration is available unless event is sold out.

Packet Pick-up

Friday – Nov. 6th- 3:00pm - 7:00pm

Winter Garden Police Department- 110 Henderson St., Winter Garden, FL 34787 (North Side Entrance)

Race Morning:

Saturday – November 7th

Location: Newton Park – 1 Surprise Drive Winter Garden, FL 34787

Late Registration & Packet Pick Up starts at 6:15 AM - (Must register thru Runsignup.com)

5k Start: 8:00 AM

Kids fun run: Line up approx. 9:15 AM - Race time 9:30 AM (Will take place after the main event)

3.1 Miles 5k Fun Run Run Walk
1 Surprise Drive, Winter Garden, Florida, 34787, United States
OpenStreetMap Google Maps
Candy Cane Course - Orlando [runsignup.com]
Sun, Dec 13, 2026 at 9:00 AM
Description
Join us for the annual Candy Cane Course 5k/10k/15k! A fun, Christmas-themed event that is perfect for the whole family.

The fun includes -
- Great Swag - designer shirt & custom medal
- Chip-timing...
Join us for the annual Candy Cane Course 5k/10k/15k! A fun, Christmas-themed event that is perfect for the whole family.

The fun includes -
- Great Swag - designer shirt & custom medal
- Chip-timing with live results and awards
- Free photos
- Delicious Treats waiting at the finish line
- Plenty of fun!
Grab your friends and family, you are not going to want to miss this one!

Can't make the race? No problem! We offer a virtual race option where you can run anywhere, at any time, and still earn the fun swag!

*Youth-based pricing for the 5k/10k, 12 & Under are only $22!
- 5k/10k/15k registration includes a custom bib, designer shirt, and an awesome finisher medal!
- 1 Mile registration is untimed and includes a custom bib, designer shirt, and an awesome finisher medal!
- The kid's dash is a fun, untimed dash for our kiddos ages 10 and under. Registration includes a mini bib, youth-sized shirt, and a specifically crafted medal for our kids' dash event! (If your child wants to run the kid's dash, and doesn't want the SWAG, they are welcome to run with us on race day for free!)
*Register by midnight on Thursday, two Thursdays before race day, to guarantee your shirt!
1 Miles 3.1 Miles 6.2 Miles 7.4 Miles Run Virtual
TBD, Winter Garden, Florida, 34711, United States
OpenStreetMap Google Maps

5 running, fun run, and walking events in Winter Garden, Florida

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Local Clubs & Organizations