Events in Winter Park, Florida | 2026-2027

Sunshine Double [runsignup.com]

Sat, May 02, 2026 at 6:00 AM

Description

Dates: Saturday, May 2, 2025 and Sunday, May 3, 2025

Place: Cady Way Park, 2529 Cady Way, Winter Park, FL 32792

What: Sunshine Double-- 50K, Marathon, Half marathon, 10K, and 5K each day. Small,...

Dates: Saturday, May 2, 2025 and Sunday, May 3, 2025

Place: Cady Way Park, 2529 Cady Way, Winter Park, FL 32792

What: Sunshine Double-- 50K, Marathon, Half marathon, 10K, and 5K each day. Small, friendly events on a flat, paved, partly shaded bike/running path.Convenient parking.

Start Times: Marathon, Half Marathon, and 50K -- 6:00 am; 5K and 10K -- 7:00

Time limit: 9.5 hours (...or so)

Parking: Cady Way Park. (Look for the Cady Way Pool.) GPS coordinates: N 28.59458, W -081.31670. There is ample parking near race start finish, and right on the course. Also, there is an overflow parking lot nearby and a school across the street. All locations are convenient.

WAIT! Before you register, read everything below. Here are the main points:

Races are not chip timed. We are old-fashioned hand timed.

Courses are not certified. No Boston qualifier.

No age group awards, no t-shirts, no useless bling.

Cupless—bring your own bottle

STOP! Read more before you sign up. These events are no frills, low-key, casual, but FUN events. Great for first timers. Convenient parking, both for the runner and for supporters. These are NOT certified courses—meaning, among other thing, NOT a Boston qualifier. Don’t expect much fancy stuff. Our basics are outstanding, though.

You DON’T get: t-shirt, hat, socks, or any other apparel, great bling (actually, any bling), cute reusable race bag, age group awards, spectators lining the course, crowds cheering you in, hot food at the finish, exciting music, and a party afterward, all on a certified course. There are plenty of other events that have those things.

You DO get: low entry fees (which is why you don't get that other stuff), convenient parking, courses that are guaranteed not short, a simple-but-nice finisher’s medal, a generous time limit, and a published finish time. But isn’t that all you really need? You know you want to sign up.

COURSES: The courses are lap courses, meaning that you’ll do a short loop multiple times. Not as boring as it might sound because you’ll see other runners going and coming, and you pass the start/finish and bathrooms each lap. The paved, urban run/bike trail is flat and largely shaded. These are open courses, and include two street crossings each lap. You are responsible for crossing safely. More course details can be found under Detailed Course Descriptions above.

-- The lap for the marathon, half marathon, and 50K is approximately 2.2 miles. The full marathon is twelve laps, the half is six laps, and the 50K is fourteen laps plus two short laps at the end.

-- The lap for the 5K and 10K is approximately 1.55 miles—two laps for the 5K and four laps for the 10K.

Turn-arounds for each distance will be clearly marked. We will have rubber bands to help you keep track of your laps.

START / FINISH / AID STATION: The only aid station is at the start/finish location, which you will pass twice each lap. We will provide chilled water, Gatorade, soda, and sweet and salty snacks.

CUPLESS: This is a cupless race. Meaning we would like for you to bring your own hydration device—water bottle, hydration belt/pack. There will be a table for your water bottles. We'll have small paper cups, but you'd be better off with your own bottle(s).

HEAT: Florida is typically hot and humid. We will provide ice for your water, Gatorade, and soda. There will also be a bucket of ice water for you to dip your hat, cooling towel, etc. We will have pickles and pickle juice, as well as a variety of salty snacks.

BATHROOMS: The bathrooms are a little walk from the start/finish, but you’ll pass them during each lap. They're inside, permanent structure bathrooms with soap and water!

LIGHT: It will be just starting to break daylight at the start, but still dark in places on the course. (Sunrise is at 6:44.) We recommend you have a light for the first half hour.

DROP BAG: The start/finish is in a small pavilion, where you may leave a drop bag.

FINISH LINE: When you finish, ring the bell, or be sure to let the timer know you’re finished. Without this, you won’t get a finish time—or at least not an accurate time. Remember we are hand-timed—no timing chips! We won't know to record your time if you don't tell us you're done.

NOW, if you are STILL undecided (congratulations for reading this far), and you want to know what to expect, we won’t likely have world class athletes based on speed, but we will likely have world class athletes based on numbers of marathons completed. Think four-digit numbers. Just imagine the stories! These experienced runners love to meet new runners and offer encouragement and wisdom.

VOLUNTEERS: We always need volunteers. Each full volunteer day earns a free long run (half marathon or full marathon) or two short runs (5K or 10K). Email me at bettiemw@gmail.com.

BMW Running Company

3.1 Miles 6.2 Miles 13.1 Miles 26.2 Miles 31 Miles Run Trail Walk

2529 Cady Way, Winter Park, Florida, 32792, United States
OpenStreetMap Google Maps

Treat Trot-Orlando [runsignup.com]

Sat, Jun 06, 2026 at 7:00 AM

Description

Every Registration Includes

Great Swag - designer shirt

Custom medal

Chip-timing with live results and awards

Free photos

Great snacks at the finish line!

Plenty of fun!

Grab your friends and family, you are not going to want to miss this one!

*Youth-based pricing for the 5k/10k, 12 & Under are only $17!

*Register by midnight on Thursday, two Thursdays before race day, to guarantee your shirt!

3.1 Miles 6.2 Miles 15k Run

TBD, Winter Park, Florida, 32789, United States
OpenStreetMap Google Maps

Independence Double [runsignup.com]

Sat, Jun 27, 2026 at 5:00 AM

Description

Low-key, no frills 5K, 10K, Half Marathon, Marathon, and 50K for two days (Saturday and Sunday).

3.1 Miles 6.2 Miles 13.1 Miles 26.2 Miles 31.06 Miles Run

2529 Cady Way, Winter Park, Florida, 32792, United States
OpenStreetMap Google Maps

Heatwave Half Marathon - Orlando [runsignup.com]

Sun, Jul 26, 2026 at 7:00 AM

Description

Join us for the Heatwave Half Marathon, 10K, & 5K!

A sun-soaked summer challenge that’s perfect for the whole family.

The fun includes –

Great Swag – designer shirt & custom medal
Chip-timing...

Join us for the Heatwave Half Marathon, 10K, & 5K!

A sun-soaked summer challenge that’s perfect for the whole family.

The fun includes –

Great Swag – designer shirt & custom medal
Chip-timing with live results and awards
Free photos
FREE ice cream at the finish to help you cool off
Plenty of hot fun in the summer sun!

Grab your friends and family—you won’t 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 is available: ages 12 & under are only $17!

Half Marathon/10K/5K 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!

Kid’s Dash is a fun, untimed dash for ages 10 and under. Registration includes a mini bib, youth-sized shirt, and a specially crafted medal for our youngest runners! (If your child wants to run the kid’s dash without swag, they’re welcome to run free on race day!)

Register by midnight on Thursday, two Thursdays before race day, to guarantee your shirt!

1 Miles 5k 10k 13.1 Miles Half Marathon Run Virtual

TBD, Winter Park, Florida, 32789, United States
OpenStreetMap Google Maps

Summer Sizzler- Orlando [runsignup.com]

Sat, Aug 08, 2026 at 7:00 AM

Description

Join us for the annual Summer Sizzler 5k/10k/15k! A fun summer event that is perfect for the whole family.

The fun includes -

Great Swag - designer shirt & custom medal
Chip-timing with live...

Join us for the annual Summer Sizzler 5k/10k/15k! A fun summer 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
FREE Kona Ice
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!

5k/10k/15K registration includes a custom bib, designer shirt, and a custom finisher medal!
1 Mile registration is untimed and includes a custom bib, designer shirt, and a custom 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!

🏁🏅Create a team, or join an existing team during registration. Once 4 people have registered on that team, all team members will be refunded $5, once ten people register another $5 will be refunded for a total of $10!

1 Miles 6.2 Miles Run Virtual

TBD, Winter Park, Florida, 32789, United States
OpenStreetMap Google Maps

Labor Day Triple [runsignup.com]

Sat, Sep 05, 2026 at 5:00 AM

Description

LABOR DAY TRIPLE: August 30, August 31, and September 1, 2025 (Labor Day Weekend)

PLACE: Cady Way Park (Trailhead), 2529 Cady Way, Winter Park, FL 32792

WHAT: Labor Day Triple--50K, Marathon, Half...

LABOR DAY TRIPLE: August 30, August 31, and September 1, 2025 (Labor Day Weekend)

PLACE: Cady Way Park (Trailhead), 2529 Cady Way, Winter Park, FL 32792

WHAT: Labor Day Triple--50K, Marathon, Half marathon, 10K, and 5K each day

(Five distance for three days. Yes, people do run three days consecutively)

START TIMES: Marathon and 50K -- 5:00 am; Half Marathon -- 5:10 am; 5K and 10K -- 6:00 am

TIME LIMIT: 9 hours (or so)

PARKING: Cady Way Park. GPS coordinates: N 28.59458, W -081.31670. Also, there is an overflow

parking lot nearby and a school across the street. All locations are convenient.

WARNING: Before you register, Read everything below. Here are the main points:

Not chip-timed. We are hand-timed. Let us know when you finish.
Courses not certified. Not designed for speed. NOT a Boston qualifier.
No age group awards, no t-shirts, no bling.
Cupless—bring your own bottle.
For 50K, marathon and half marathon you’ll need a light

Now, if you haven’t tuned out yet, be advised these events are no frills, low-key, casual, fun events. GREAT for first timers, maybe not so great for a PR. This is not a certified or sanctioned course—meaning, among other thing, NOT a Boston qualifier. Don’t expect much and maybe you won’t be disappointed.

WHAT YOU DON’T GET: t-shirt, hat, socks, or any other apparel, great bling (actually, any bling), cute reusable race bag, age group awards, spectators lining the course, crowds cheering you in, hearty food at the finish, exciting music, and a party afterward, all on a certified course. There are plenty of other events out there for you.

WHAT YOU DO GET: low entry fees, courses that are guaranteed not short, a simple finisher’s medal, a generous time limit, and a published finish time. But isn’t that all you really need? What do you do with all that other stuff anyway? You know you want to sign up. Really, where else can you run a marathon for $65?

COURSES: The courses are NOT certified--no Boston qualifier here. The courses are lap courses, meaning that you’ll do a double out-and-back multiple times. Which means you’ll see other runners going and coming. Not as boring as it might sound. In fact, many people come to prefer this course design. The paved, urban run/bike trail is flat and largely shaded. This is an open course, and includes two street crossings each lap. You are responsible for crossing safely. See Detailed Course Descriptions above for more details.

The marathon and half marathon lap is approximately 2.2 miles. The full is twelve laps and the half is six laps. The 5K and 10K lap is approximately 1.55 miles—two laps for the 5K and four laps for the 10K. The 50K is fourteen marathon laps, with two small laps added at the end.

Turn arounds for each distance will be clearly marked. Rubber bands will be available to help you keep track of your laps.

For more details and a crude course map, see Detailed Course Description above.

FINISH: When you finish, be sure to ring the bell and make sure the timer knows you are finished. Otherwise, you won't get an accurate time. Remember we are hand-timed.

AID STATION: The aid station is at the start/finish of the loop course, which you will pass two times each lap. We will provide plenty of water, Gatorade, and soda, along with a variety of sweet and salty snacks. This is a cupless race. Bring your own hydration device—water bottle, hydration belt/pack.

HEAT: Florida is typically hot and humid. We will provide ice for your water/Gatorade, hat, water bottle, etc. We will also have ice water in a bucket for you to dip your hat, cooling towel, etc. We will also have pickles, olives, and pickle juice, as well as a variety of salty snacks.

LIGHT: Marathoners, 50Kers, and half marathoners will need a light for the first couple of hours. It won’t get light until around 6:40.

BATHROOMS: The bathrooms are a little walk from the start/finish, but you’ll pass them during each lap.

DROP BAG: The start/finish is in a small pavilion, where you may leave a drop bag.

If you are still undecided (congratulations for reading this far), and you want to know what to expect, we won’t likely have world class athletes based on speed, but we will likely have world class athletes based on numbers of marathon completed. We have had at least five people who are at the top of the Mega Marathon List. Think four-digit numbers. Just imagine the stories!

VOLUNTEERS: We always need volunteers. Each volunteer day earns one free race entry for a long distance (50K, marathon, half marathon), or two free entries for a short distance (5K or 10K). Contact Bettie at bettiemw@gmail.com. You may use the free entry yourself or for someone else.

BMW Running Company

3.1 Miles 6.2 Miles 13.1 Miles 26.2 Miles 31 Miles Run Trail Walk

2529 Cady Way, Winter Park, Florida, 32792, United States
OpenStreetMap Google Maps

Golden Harvest Half Marathon & 5k/10k - Orlando [runsignup.com]

Sun, Sep 27, 2026 at 7:00 AM

Description

Join us for the annual Hometown Half Marathon & 5k/10k! A run local-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 Hometown Half Marathon & 5k/10k! A run local-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
Pacers for the half marathon
Free photos
Delicious Treats waiting at the finish line
Plenty of fun!

*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!
10k registration includes a custom bib, designer shirt, and an awesome finisher medal!
5k 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 5k 6.2 Miles 10k 13.1 Miles Half Marathon Run

TBD, Winter Park, Florida, 32789, United States
OpenStreetMap Google Maps

Holiday Five [runsignup.com]

Sun, Dec 27, 2026 at 6:00 AM

Description

PLACE: 2529 Cady Way, Winter Park, FL 32792

DESCRIPTION: Holiday Five, December 27, 28, 29, 30, 31, 2025

What: 5 Distances, 5 days. 50K, Marathon, Half marathon, 10K, and 5K each day.

Where: Cady Way...

PLACE: 2529 Cady Way, Winter Park, FL 32792

DESCRIPTION: Holiday Five, December 27, 28, 29, 30, 31, 2025

What: 5 Distances, 5 days. 50K, Marathon, Half marathon, 10K, and 5K each day.

Where: Cady Way Trail Head, 2529 Cady Way, Winter Park, FL 32792

Start Times: 50K, Marathon, and Half marathon—6:00 am; 5K and 10K—7:00 am.

Time limit: 9.5 hours (or so)

Parking: Cady Way Trailhead, near the Cady Way Pool. GPS coordinates:

N 28.59458, W -081.31670

WARNING: Before you continue, be warned that these are low-key, bare bones, casual events. Set your expectations low—very low—so that your disappointment will be minimal. But wait! We have easy logistics, great course, and an abundance of friendliness. Also, very convenient parking—pass your car every lap. If you’re still interested, here’s what to expect.

You WILL NOT get age group awards, a cleverly designed t-shirt or hat, great bling (actually, any bling), cute reusable race bag filled with goodies, spectators lining the course, crowds cheering you in, hearty food at the finish, exciting music, or a party afterward.

You WILL get low entry fees, courses that are guaranteed not short, a nice finisher’s medal, basic support (see below), a VERY generous time limit, and lots of friendly support from staff and runners. Also, convenient locations for supporters.

Start/Finish and Aid Station: The start and finish are in a small pavilion, where you may leave a drop bag. This is also the aid station, which you will pass twice each lap. (More about laps below.) We will provide water, Gatorade, sodas, and light sweet and salty snacks, including pickles and pickle juice.

Courses: The paved, urban run/bike trail is flat and partly shaded. This is an open course, and includes two street crossings. You are responsible for crossing safely. The 50K/marathon/half marathon course is a double out-and-back loop of approximately 2.2 miles; marathon 12 loops, half marathon 6 loops, 50K 14 loops plus 2 "baby" loops. The 5K/10K course is approximately 1.55 miles, 2 and 4 loops respectively. Turn arounds will be clearly marked. The trail is popular with local residents, so be prepared to share. For more information about the courses, see Detailed Course Description above.

Finish: When you are finished, ring the bell at the timing table and let the timer know you're finished. That's the only way to get an accurate time. Remember we are hand-timed. If you don't tell us, we won't know.

Cupless: Bring your own hydration device—water bottle, hydration belt/pack. There will be a table at the start/finish for your bottles. (We will have small cups for the soda.)

Light: If you start at 6:00, you will need a light for the first half hour.

Volunteers Needed: Each volunteer day earns a free race entry for yourself or someone else for either one long race (50K, marathon, or half marathon) or for two short races (5K or 10K). Contact Bettie at bettiemw@gmail.com.

BMW Running Company

3.1 Miles 6.2 Miles 13.1 Miles 26.2 Miles 31 Miles Run Trail

Cady Way Trail Head, Winter Park, Florida, 32792, United States
OpenStreetMap Google Maps

9 running events in Winter Park, Florida

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Local Clubs & Organizations