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

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

calendar_today February 18, 2027 location_on Day 1 - TBD; Day 2 - Kit Land Nelson Park, Apopka; Day 3 - Chapin Station, Winter Garden; Day 4 - TBD; & Day 5 - Cady Way Park, Winter Park., Apopka, Central Florida 32703

About This Event

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) - TBD

               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 Road, Winter Garden, FL 34787: Google Maps GPS: 28.582556, -81.567394  

               Day 4 (2/21) - TBD

              Day 5 (2/22) - Cady Way Park (Trailhead), 2529 Cady Way, Winter Park, FL 32792: Google Maps GPS: 28.593650, -81.316796

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:            All race distances start at 7:00 am

TIME LIMIT:                9.5 hours (or so)

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 events are no frills, 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, 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 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, with two small laps added 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.

Wingman Running Company

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Frequently Asked Questions

When is Florida Five (Five Days, Five Different Locations, Five Distances to choose from) 2027?
Florida Five (Five Days, Five Different Locations, Five Distances to choose from) takes place on Thursday, February 18, 2027 in Apopka, Florida.
Where does Florida Five (Five Days, Five Different Locations, Five Distances to choose from) take place?
Florida Five (Five Days, Five Different Locations, Five Distances to choose from) is held at Day 1 - TBD; Day 2 - Kit Land Nelson Park, Apopka; Day 3 - Chapin Station, Winter Garden; Day 4 - TBD; & Day 5 - Cady Way Park, Winter Park. in Apopka, Florida (Central Florida). See the course maps section on this page for route details where available.
How do I register for Florida Five (Five Days, Five Different Locations, Five Distances to choose from)?
Registration is online — use the Register button on this page to sign up through the race's official registration page. Registering early usually means lower entry fees.
Is there a promo code for Florida Five (Five Days, Five Different Locations, Five Distances to choose from)?
Discounts are set by the race organizer and appear on the official registration page when active. The most reliable way to pay less is registering early — most Florida races raise prices as race day gets closer.

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calendar_today February 18, 2027
location_on Day 1 - TBD; Day 2 - Kit Land Nelson Park, Apopka; Day 3 - Chapin Station, Winter Garden; Day 4 - TBD; & Day 5 - Cady Way Park, Winter Park., Apopka, Central Florida 32703
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Local Running Stores

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Clermont, Central Florida

Dash Sports is Clermont's specialty running and walking shoe store, serving the South Lake County running community from its location on West Montrose Street in downtown Clermont. The store takes a thorough approach to fitting — each customer receives a custom gait and foot analysis that typically runs 20 to 40 minutes, ensuring the shoe recommendation is grounded in how you actually move. Clermont's reputation as a triathlon and endurance sports hub makes Dash Sports a natural resource for serious athletes alongside everyday runners and walkers. The store carries a strong lineup of performance brands including Hoka, On Running, Brooks, New Balance, and Altra, giving customers access to the leading options in road, trail, and stability footwear. Dash Sports also stocks Olukai and Aetrex for customers seeking comfort and orthopedic options alongside performance footwear — rounding out a selection that serves runners, walkers, and recovery-focused athletes alike.

phone (352) 394-7434 language Visit Website
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Altamonte Springs, Central Florida

Fit2Run Altamonte Springs is located in Altamonte Mall, bringing the Runner's Superstore experience to Seminole County. Offering gait analysis, top performance footwear, and community run events for the growing north Orlando running community.

phone (844) 348-2786 language Visit Website
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Lake Buena Vista, Central Florida

Fit2Run at Disney Springs is the only running specialty store inside the Walt Disney World Resort destination. Open late to serve resort guests and locals alike, offering gait analysis, top performance brands, and a one-of-a-kind running store experience in the heart of Central Florida tourism.

phone (407) 743-5990 language Visit Website
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Florida Five (Five Days, Five Different Locations, Five Distances to choose from)

February 18, 2027

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