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

  • Date Thu 18th February 2027 - Mon 22nd February 2027
  • Time 7:00AM EST
  • Location Winter Park, Apopka, Winter Garden, Union Park & Orlando, Florida
  • Price $32.80 - $316.00
  • Races 30 races
  • Distances Ultra, Marathon, Half Marathon

Event summary

Get ready for an unforgettable running experience at the Florida Five, taking place from February 18 to February 22, 2027, in the beautiful Central Florida region! This five-day event offers a unique opportunity for runners and walkers of all levels to participate in five different locations, with a variety of race distances to choose fromβ€”50K, Marathon, Half-Marathon, 10K, and 5K. Each day features a scenic course set within 35 miles of Orlando International Airport (MCO), ensuring easy access for participants traveling from afar.

Kick off the festivities at Cady Way Park in Winter Park on February 18, then continue the adventure through Apopka, Winter Garden, Union Park, and conclude in Orlando. With race start times at 7 a.m. (8 a.m. on the final day), participants can enjoy a casual, low-key atmosphere without the pressure of chip timing or age group awards. Whether you choose to tackle one day or conquer all five, the Florida Five promises fun, camaraderie, and a chance to embrace the joy of running in Florida’s invigorating winter climate. Don’t miss this chance to challenge yourself and connect with fellow running enthusiasts!

Organiser's Description

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-LESSbring your own bottle.

These are low-key, casual, fun events. GREAT for first timers! These ARE NOT CERTIFIED OR SANCTIONED coursesmeaning, NOT a Boston qualifier. Dont expect much and maybe you wont be disappointed.

WHAT YOU DONT 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 finishers medal, a generous time limit, and a published finish time. But isnt 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 milestwo 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 devicewater 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 youll 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 youre finished. Without this, you wont get a finish timeor at least not an accurate time. Remember we are hand-timedno 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 wont 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

Races

  • Florida Five Day 1 - 50K

    Incl. $5.50 Fee

    Thu 18th February 2027 (7:00AM EST)

    $80.50

    Cady Way Park (Trailhead), 2529 Cady Way, Winter Park, FL 32792: Google Maps GPS: 28.593650, -81.316796
  • Florida Five Day 1 - Marathon

    Incl. $4.90 Fee

    Thu 18th February 2027 (7:00AM EST)

    $69.90

    Cady Way Park (Trailhead), 2529 Cady Way, Winter Park, FL 32792: Google Maps GPS: 28.593650, -81.316796
  • Florida Five Day 1 - Half Marathon

    Incl. $4.30 Fee

    Thu 18th February 2027 (7:00AM EST)

    $59.30

    Cady Way Park (Trailhead), 2529 Cady Way, Winter Park, FL 32792: Google Maps GPS: 28.593650, -81.316796
  • Florida Five Day 1 - 10K

    Incl. $3.40 Fee

    Thu 18th February 2027 (7:00AM EST)

    $43.40

    Cady Way Park (Trailhead), 2529 Cady Way, Winter Park, FL 32792: Google Maps GPS: 28.593650, -81.316796
  • Florida Five Day 1 - 5K

    Incl. $2.80 Fee

    Thu 18th February 2027 (7:00AM EST)

    $32.80

    Cady Way Park (Trailhead), 2529 Cady Way, Winter Park, FL 32792: Google Maps GPS: 28.593650, -81.316796
  • Florida Five Day 2 - 50K

    Incl. $5.50 Fee

    Fri 19th February 2027 (7:00AM EST)

    $80.50

    Kit Land Nelson Park, 10 N. Forest Ave, Apopka, FL 32703: Google Maps GPS: 28.676821, -81.507628
  • Florida Five Day 2 - Marathon

    Incl. $4.90 Fee

    Fri 19th February 2027 (7:00AM EST)

    $69.90

    Kit Land Nelson Park, 10 N. Forest Ave, Apopka, FL 32703: Google Maps GPS: 28.676821, -81.507628
  • Florida Five Day 2 - Half Marathon

    Incl. $4.30 Fee

    Fri 19th February 2027 (7:00AM EST)

    $59.30

    Kit Land Nelson Park, 10 N. Forest Ave, Apopka, FL 32703: Google Maps GPS: 28.676821, -81.507628
  • Florida Five Day 2 - 10K

    Incl. $3.40 Fee

    Fri 19th February 2027 (7:00AM EST)

    $43.40

    Kit Land Nelson Park, 10 N. Forest Ave, Apopka, FL 32703: Google Maps GPS: 28.676821, -81.507628
  • Florida Five Day 2 - 5K

    Incl. $2.80 Fee

    Fri 19th February 2027 (7:00AM EST)

    $32.80

    Kit Land Nelson Park, 10 N. Forest Ave, Apopka, FL 32703: Google Maps GPS: 28.676821, -81.507628
  • Florida Five Day 3 - 50K

    Incl. $5.50 Fee

    Sat 20th February 2027 (7:00AM EST)

    $80.50

    Chapin Station, 501 Crown Point Cross Road, Winter Garden, FL 34787: Google Maps GPS: 28.582556, -81.567394
  • Florida Five Day 3 - Marathon

    Incl. $4.90 Fee

    Sat 20th February 2027 (7:00AM EST)

    $69.90

    Chapin Station, 501 Crown Point Cross Road, Winter Garden, FL 34787: Google Maps GPS: 28.582556, -81.567394
  • Florida Five Day 3 - Half Marathon

    Incl. $4.30 Fee

    Sat 20th February 2027 (7:00AM EST)

    $59.30

    Chapin Station, 501 Crown Point Cross Road, Winter Garden, FL 34787: Google Maps GPS: 28.582556, -81.567394
  • Florida Five Day 3 - 10K

    Incl. $3.40 Fee

    Sat 20th February 2027 (7:00AM EST)

    $43.40

    Chapin Station, 501 Crown Point Cross Road, Winter Garden, FL 34787: Google Maps GPS: 28.582556, -81.567394
  • Florida Five Day 3 - 5K

    Incl. $2.80 Fee

    Sat 20th February 2027 (7:00AM EST)

    $32.80

    Chapin Station, 501 Crown Point Cross Road, Winter Garden, FL 34787: Google Maps GPS: 28.582556, -81.567394
  • Florida Five Day 4 - 50K

    Incl. $5.50 Fee

    Sun 21st February 2027 (7:00AM EST)

    $80.50

    Blanchard Park, 2451 Dean Rd, Union Park, FL 32817: Google Maps GPS: 28.578660, -81.243468
  • Florida Five Day 4 - Marathon

    Incl. $4.90 Fee

    Sun 21st February 2027 (7:00AM EST)

    $69.90

    Blanchard Park, 2451 Dean Rd, Union Park, FL 32817: Google Maps GPS: 28.578660, -81.243468
  • Florida Five Day 4 - Half Marathon

    Incl. $4.30 Fee

    Sun 21st February 2027 (7:00AM EST)

    $59.30

    Blanchard Park, 2451 Dean Rd, Union Park, FL 32817: Google Maps GPS: 28.578660, -81.243468
  • Florida Five Day 4 - 10K

    Incl. $3.40 Fee

    Sun 21st February 2027 (7:00AM EST)

    $43.40

    Blanchard Park, 2451 Dean Rd, Union Park, FL 32817: Google Maps GPS: 28.578660, -81.243468
  • Florida Five Day 4 - 5K

    Incl. $2.80 Fee

    Sun 21st February 2027 (7:00AM EST)

    $32.80

    Blanchard Park, 2451 Dean Rd, Union Park, FL 32817: Google Maps GPS: 28.578660, -81.243468
  • Florida Five Day 5 - 50K

    Incl. $5.50 Fee

    Mon 22nd February 2027 (7:00AM EST)

    $80.50

    Barnett Park, 4801 W. Colonial Drive, Orlando, FL 32808: Google Maps GPS: 28.562040, -81.439746
  • Florida Five Day 5 - Marathon

    Incl. $4.90 Fee

    Mon 22nd February 2027 (7:00AM EST)

    $69.90

    Barnett Park, 4801 W. Colonial Drive, Orlando, FL 32808: Google Maps GPS: 28.562040, -81.439746
  • Florida Five Day 5 - Half Marathon

    Incl. $4.30 Fee

    Mon 22nd February 2027 (7:00AM EST)

    $59.30

    Barnett Park, 4801 W. Colonial Drive, Orlando, FL 32808: Google Maps GPS: 28.562040, -81.439746
  • Florida Five Day 5 - 10K

    Incl. $3.40 Fee

    Mon 22nd February 2027 (7:00AM EST)

    $43.40

    Barnett Park, 4801 W. Colonial Drive, Orlando, FL 32808: Google Maps GPS: 28.562040, -81.439746
  • Florida Five Day 5 - 5K

    Incl. $2.80 Fee

    Mon 22nd February 2027 (7:00AM EST)

    $32.80

    Barnett Park, 4801 W. Colonial Drive, Orlando, FL 32808: Google Maps GPS: 28.562040, -81.439746
  • Florida Five All Five Days - 50K

    Incl. $16.00 Fee

    Thu 18th February 2027 (7:00AM EST)

    $316.00

    Day 1: Cady Way Park (Trailhead), 2529 Cady Way, Winter Park Day 2: Kit Land Nelson Park, 10 N. Forest Ave, Apopka Day 3: Chapin Station, 501 Crown Point Cross Road, Winter Garden Day 4: Blanchard Park, 2451 Dean Rd, Union Park Day 5: Barnett Park, 4801 W. Colonial Drive, Orlando
  • Florida Five All Five Days - Marathon

    Incl. $14.00 Fee

    Thu 18th February 2027 (7:00AM EST)

    $274.00

    Day 1: Cady Way Park (Trailhead), 2529 Cady Way, Winter Park Day 2: Kit Land Nelson Park, 10 N. Forest Ave, Apopka Day 3: Chapin Station, 501 Crown Point Cross Road, Winter Garden Day 4: Blanchard Park, 2451 Dean Rd, Union Park Day 5: Barnett Park, 4801 W. Colonial Drive, Orlando
  • Florida Five All Five Days - Half Marathon

    Incl. $14.20 Fee

    Thu 18th February 2027 (7:00AM EST)

    $234.20

    Day 1: Cady Way Park (Trailhead), 2529 Cady Way, Winter Park Day 2: Kit Land Nelson Park, 10 N. Forest Ave, Apopka Day 3: Chapin Station, 501 Crown Point Cross Road, Winter Garden Day 4: Blanchard Park, 2451 Dean Rd, Union Park Day 5: Barnett Park, 4801 W. Colonial Drive, Orlando
  • Florida Five All Five Days - 10K

    Incl. $10.60 Fee

    Thu 18th February 2027 (7:00AM EST)

    $170.60

    Day 1: Cady Way Park (Trailhead), 2529 Cady Way, Winter Park Day 2: Kit Land Nelson Park, 10 N. Forest Ave, Apopka Day 3: Chapin Station, 501 Crown Point Cross Road, Winter Garden Day 4: Blanchard Park, 2451 Dean Rd, Union Park Day 5: Barnett Park, 4801 W. Colonial Drive, Orlando
  • Florida Five All Five Days - 5K

    Incl. $8.20 Fee

    Thu 18th February 2027 (7:00AM EST)

    $128.20

    Day 1: Cady Way Park (Trailhead), 2529 Cady Way, Winter Park Day 2: Kit Land Nelson Park, 10 N. Forest Ave, Apopka Day 3: Chapin Station, 501 Crown Point Cross Road, Winter Garden Day 4: Blanchard Park, 2451 Dean Rd, Union Park Day 5: Barnett Park, 4801 W. Colonial Drive, Orlando

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Location

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, Winter Park, Apopka, Winter Garden, Union Park & Orlando, 32703, FL, United States

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Feb 18, 2027

$32.80 - $316.00