Run VibesBeta

Race profile

Holiday Five

50K · Marathon · Half Marathon · 10K · 5K · 2.2 mi · 1.6 mi

Dec 31, 2026 · Winter Park, Florida, US

Listed Jan 7, 2023

The read

Run Vibes summary

Summarization pending

AI summarization pending

We haven’t generated Run Vibes’ quick-read summary for this race yet—it’s in the enrichment queue and will appear here soon with notes on vibe, race-day feel, and who the event suits best.

Until then, open Original listing below for the full source description, and double-check anything important on the organizer’s page.

Original listingFull description from sourceExpand the official listing text (unchanged)

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

More races

More events in Florida, and comparable distances or challenge.

Game On! Run Singer Island

Half Marathon · 10K · Walk

3/28/2026 · Riviera Beach, FL

Listed Dec 29, 2018

Register
ScenicSteady EffortAwardsMedalsShirt

Experience the stunning coastal beauty of Singer Island with this popular Half Marathon and 10K, featuring breathtaking views, charming communities, and a course for all levels.

Florida Shamrock Distance Classic

Half Marathon · 10K · 5K · 1 mi

3/28/2026 · Saint Petersburg, FL

Listed May 25, 2022

Register
Festive SeasonalPush PotentialBeginner-friendlyScenic

Go green and chase a PR on the fast, flat courses of the Shamrock Distance Classic at Fort De Soto Park, offering distances from a mile to a half marathon.

4th Bonnet Springs Park 5k | Lakeland, FL

5K · Fun Run · 0.3 mi

3/28/2026 · Lakeland, FL

Listed Dec 18, 2022

Register
Cause DrivenEasygoingBeginner-friendly

Join the 4th Bonnet Springs Park 5k in Lakeland, FL, a family-friendly event supporting community enrichment through nature, culture, and recreation.

Amazing Race: Chamber Series

5 mi

3/28/2026 · New Smyrna Beach, FL

Listed Sep 8, 2025

Register
QuirkyPush PotentialBeginner-friendlyFestiveCause-driven

Teams of two will navigate 5 miles through New Smyrna Beach, tackling 20+ fun and challenging obstacles, puzzles, and physical feats in this inaugural adventure race.

FROM WASTE TO RACE 5K& 10K! powered by Commissioner Juan Carlos "JC" Bermudez

Walk · 5K · 10K

3/28/2026 · Miami, FL

Listed Jan 27, 2025

Register
Cause DrivenSteady EffortBeginner-friendlyFestive

Join the From Waste to Race 5K or 10K in Miami, a unique event transforming a greenspace into a running destination while promoting environmental stewardship on new trail/gravel terrain.

Kids Run This 'Hood 5k

5K · Fun Run · 0.5 mi

3/28/2026 · Tampa, FL

Listed Nov 17, 2024

Register
Cause DrivenEasygoingBeginner-friendlyQuirky

A community-focused 5k and vibrant kids' color run, organized by local PTAs to support Hillsborough County schools, complete with chip timing and a post-race celebration.

Lead with Love 5K

5K · 2 mi · 0.8 mi · Walk

3/28/2026 · West Palm Beach, FL

Listed Feb 27, 2022

Register
Cause DrivenEasygoingBeginner-friendlyFestiveAwards

Support mental wellness at the 5th Annual Lead with Love 5K in West Palm Beach, featuring a scenic park route, unique wellness activities, and a welcoming atmosphere for all ages.

The Cow Patty 5k

5K

3/28/2026 · Sarasota, FL

Listed Dec 18, 2025

Register
FunSteady EffortBeginner-friendlyScenic

A quirky 5k trail run through pastures and woods in Sarasota, aiming for family fun while supporting an orphanage in Kenya.