Florida Five (Five Days, Five Different Locations, Five Distances to choose from) logo

Florida Five (Five Days, Five Different Locations, Five Distances to choose from)

Florida Five (Five Days, Five Different Locations, Five Distances to choose from) is a running race on February 18–22, 2027 in Winter Park, Apopka, Winter Garden, Union Park & Orlando, FL, with entry fees from $30 to $300.

Date
February 18–22, 2027 (128 days to go)
Price
$30–$300
Sport
Running

From the Organizer

FLORIDA FIVE is a five-day running event across various locations in Central Florida. You can sign up for one day, multiple days, or all five days! Distances offered are 50K, Marathon, Half-Marathon, 10K and 5K. The event will run from February 18 through February 22, 2027 (The week of President's Day). Runners, walkers or run/walkers are all welcome.

PLACE: All locations will be within 35 miles from the Orlando International Airport (MCO).

               Day 1 (2/18) - Cady Way Park (Trailhead), 2529 Cady Way, Winter Park, FL 32792: Google Maps GPS: 28.593650, -81.316796

               Day 2 (2/19) - Kit Land Nelson Park, 10 N. Forest Ave, Apopka, FL 32703: Google Maps GPS: 28.676821, -81.507628

               Day 3 (2/20) - Chapin Station, 501 Crown Point Cross Rd, Winter Garden, FL 34787: Google Maps GPS: 28.582556, -81.567394  

               Day 4 (2/21) - Blanchard Park, 2451 Dean Rd, Union Park, FL 32817: Google Maps GPS: 28.578660, -81.243468

              Day 5 (2/22) - Barnett Park, 4801 W. Colonial Drive, Orlando, FL 32808: Google Maps GPS: 28.562040, -81.439746

WHAT:                         50K, Marathon, Half marathon, 10K, and 5K distance options for each day.

                                      (Five distances for five days. Yes, people can, and do run five days consecutively)

START TIMES:            Race Start times for each day:

                                      Day 1: 7 a.m.

                                     Day 2: 7 a.m.

                                     Day 3: 7 a.m.

                                     Day 4: 7 a.m.

                                     *Day 5: 8 a.m.

                                      TIME LIMIT: 9.5 hours

PARKING:                    Parking will be at each race site, specific information for each race day coming soon.

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 are not certified. Not designed for speed. NOT a Boston qualifier.
     No age group awards, no t-shirts.
     Cup-less—bring your own bottle.
     
These are low-key, casual, fun events. GREAT for first timers! These are not certified or sanctioned courses—meaning, 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, cute reusable race bag, age group awards, spectators lining the course, large crowds cheering you in, hearty food at the finish, exciting music, and a party afterward.

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 will do an out-and-back multiple times. Which means you will see other runners going and coming. Not as boring as it might sound. In fact, many people come to prefer this course design. All the courses will be on primarily paved, urban run/bike trails that are fairly flat with some to a lot of shade. These are open courses and will be open to the public. This means there may be other runners, walkers and cyclists. Detailed course descriptions will be coming soon!

The marathon and half marathon laps will be approximately 1.9 to 2.2 miles. The full is expected to be 12 to 14 laps and the half is expected to be 6 to 7 laps. The 5K and 10K laps are approximately 1.55 miles—two laps for the 5K and four laps for the 10K. The 50K is expected to be 14 to 16 marathon laps, plus one small lap at the end. 

Turn around for each distance will be clearly marked. Rubber bands will be available 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 7:00.)  We recommend you have a light for the first half hour.

DROP BAG: There will be a location near the start/finish line 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 at wingmanrunning@yahoo.com

Wingman Running Company

Events

Florida Five Day 1 (Thursday) - 5K$30
Florida Five Day 1 (Thursday) - 10K$40
Florida Five Day 1 (Thursday) - Half Marathon$55
Florida Five Day 1 (Thursday) - Marathon$65
Florida Five Day 1 (Thursday) - 50K$75
Florida Five All Five Days - 5K$120
Florida Five All Five Days - 10K$160
Florida Five All Five Days - Half Marathon$220
Florida Five All Five Days - Marathon$260
Florida Five All Five Days - 50K$300

Typical Conditions

It's too far out for a forecast, so here's what weather on this date is normally like in the area. A race day forecast will replace this as race week approaches.

Typical High

76°

Typical Low

51°

Based on US Climate Normals data from Orlando W, 9 mi from the venue.

Sunrise 7:01 AMSunset 6:18 PMDaylight 11h 17m

About Winter Park, Apopka, Winter Garden, Union Park & Orlando, FL

Nearest Airport

MCO

Orlando International Airport · 18 mi

Time Zone

Eastern Time

From Endurance Grid

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About This Sport

Endurance Grid is here to help you understand the sport, decide if it’s the right fit, and learn how to prepare. For course distances, logistics, and race-day specifics, always defer to the race organizer’s event page.

With running, there's a distance for every fitness level, a community at every start line, and nothing beats the feeling of crossing a finish line you trained for.

Running is an endurance sport that rewards consistency, and showing up every week compounds in ways that will surprise you.

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Running

From 5K to marathon, running races are an accessible entry point into endurance sport. There's a distance for every fitness level and a community at every start line.

Frequently Asked Questions

What is the Florida Five (Five Days, Five Different Locations, Five Distances to choose from)?
Florida Five (Five Days, Five Different Locations, Five Distances to choose from) is a running race held in Winter Park, Apopka, Winter Garden, Union Park & Orlando, Florida on February 18, 2027. It is one of the many endurance events listed on Endurance Grid, a multi-sport endurance event calendar covering running races, triathlons, HYROX, and more endurance sports across the United States. Find more running races near you or explore our sports guides to learn what race day actually feels like.
When and where is the Florida Five (Five Days, Five Different Locations, Five Distances to choose from)?
Thursday, February 18, 2027 in Winter Park, Apopka, Winter Garden, Union Park & Orlando, Florida at Day 1 - Cady Way Park, Winter Park, FL; Day 2 - Kit Land Nelson Park, Apopka, FL; Day 3 - Chapin Station, Winter Garden, FL; Day 4 - Blanchard Park, Union Park, FL; Day 5 - Barnett Park, Orlando, FL. Check the event page for exact start times and wave schedules.
How do I register for the Florida Five (Five Days, Five Different Locations, Five Distances to choose from)?
Registration is handled through the event's registration page. Confirm pricing and distances there, and sign up.

Florida Five (Five Days, Five Different Locations, Five Distances to choose from)

Feb 18, 2027

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