Holiday Five

Cady Way Trail Head
Winter Park, FL 32792

Running > 5k, Half Marathon, Marathon

Registration Powered by RunSignUp

Event Description

WARNING: These races are low-key, bare-bones events. BUT no shirts = low fees. These are bargain hunter specials. 

What:               Holiday Five – Full marathon, Half marathon, 10K, 5K

When:              December 27 – December 31, 2023.

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

Start Times:      All distances start at 6:00. Optional late start at 7:00 only for the 10K and 5K.

Time limit:        9 hours

Parking:            In the parking lot for the Cady Way Trailhead. 

GPS coordinates: N 28.59458, W -081.31670

What you don’t get:  Certified course, cleverly designed t-shirt or hat, great bling (actually, any bling), cute reusable race bag, spectators lining the course, crowds cheering you in, hearty food at the finish, exciting music, fancy age group awards, or a party afterward.

What you do get:  Low entry fees (that don’t increase), courses that are guaranteed not short, a cheap finisher’s medal, basic support, a generous time limit, and five days of fun.

The aid station is at the start/finish of the loop course. We will provide water and Gatorade, and a few light snacks. This is a cupless race. Bring your own hydration device—water bottle, hydration belt/pack. Orlando’s weather in December is unpredictable. We could have low’s in the 20’s and high’s in the 80’s. Be prepared for anything. You must have a light. You will need it for the first hour.

Courses: The marathon is twelve out-and-back laps of approximately 2.2 miles; the half marathon course is six laps. The 5K and 10K courses are two and four laps of approximately 1.55 miles. The paved, urban run/bike trail is flat and mostly shaded. This is an open course, and includes two street crossings. You are responsible for crossing safely. Turn arounds will be clearly marked. The trail runs through a residential area, so we ask that you be quiet the first few hours.

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

(Note that the fees are simple. No early bird special, no penalty for late registrations.)

Needed: Volunteers. Each volunteer day earns a free race entry, or $60 per day. Contact Bettie at


Event Location & Accomodations

Connect on Social