The Gamble

APR
19
2026
A variable-distance loop race in Hendersonville where a dice roll at the start decides how many ~1.67 mile laps runners complete. The cupless aid station sits at the loop start and the figure-8 route includes singletrack, paved paths, stairs, and possible mud.
Sun 19 Apr 2026

Always double-check with the organizer's website! This page may contain affiliate links.

The Gamble - Hendersonville, NC

The Gamble is a variable-distance loop race held in Hendersonville, NC. The course is a roughly 1.67 mile figure-8 loop. At the start, organizers roll dice; the resulting number determines how many laps everyone will run. Participants must use only what they have on them at the start; there is no extra preparation time once laps are determined.

Distances are variable:

  • ~1.67 mile loop
  • Possible total distance: 3.33 to 20 miles

The course surface includes dirt singletrack, short paved pathways, some gravel, a few stairs, and a couple of hills. Recent rain within a couple of weeks can make sections muddy. Course marshals are stationed where the figure-8 crosses to direct runners and manage interactions with oncoming motor vehicles.

An aid station is located at the loop start/end and is cupless; participants must bring their own hydration container (for example a cup, handheld bottle, belt, or vest). Aid offerings include water, electrolytes, basic nutrition, quesadillas (vegan and dairy), snacks, and fruit. Restrooms are not directly on the course but are very close to the aid station.

Organizers state proceeds support The Run828 Foundation and North Carolina Mountain Trail Runners. NCMTR members receive free entry via a coupon code. There are no refunds. The absolute cutoff is six hours after the start; organizers may shorten that cutoff if the rolled distance is considerably shorter. The event is planned to run rain or shine, and a weather-forced cancellation would not be rescheduled. Visit the organization's website for the most recent information.

Random Distance (2 - 12 Laps)

Events nearby

A trail race day at Tryon International Equestrian Center offering marathon, half and 10K distances on a 6.5-mile loop through packed paths, single-track and meadows, with one cup-less aid station and on-site camping.
Inaugural Railway 5K and 1 Mile on the Ecusta Trail in Hendersonville, presented by Aetna, with in-person and virtual options, shirts, medals, and family-friendly amenities.
Experience a scenic 10 mile run or hike around the shores of Lake Summit on packed gravel roads. Enjoy mountain views and a pancake breakfast at the finish line in the heart of the Southern Appalachian Mountains.
An 8.5 mile trail race through DuPont State Recreational Forest near Brevard NC, with about 1,000 feet of climb and proceeds benefiting the Friends of DuPont State Forest.
Add Event
Help us complete the calendar!
  • Distance is at least 5 km
  • Event has a website or Facebook page
Website
Optional: Please provide your e-mail address if we may contact you.
Report a change
We will only update the data if the information is also on the website.