The Gamble

Hendersonville, United States • 19 Apr 2026

The Gamble : April 19, 2026

The Gamble is a running event in Hendersonville, NC. At the start the organizers roll a die. The number rolled determines how many laps each competitor runs. The loop is about 1.67 miles and runners must begin the race with whatever gear they carry.

Distances and course

  • Minimum possible distance: 3.33 miles
  • Maximum possible distance: 20 miles
    Distances are not guaranteed to be exact. The loop is a figure 8. The course includes dirt singletrack, short paved paths, hills, a few stairs, and some gravel. If it rains within a couple weeks of the event, runners should expect some mud. Course marshals will direct runners where the loop crosses itself and where the course meets roads.

Aid, entry and rules

An aid station at the loop start/end provides water, electrolytes, and basic nutrition and is cupless, so competitors must bring their own hydration container. Restrooms are not on the course but are very close to the aid station. Proceeds support the Run828 Foundation and North Carolina Mountain Trail Runners. NCMTR members receive free entry via a coupon code. No refunds are offered. The absolute cutoff for the event is six hours after the start; organizers may shorten that cutoff if the race distance is much shorter. The event is planned to run rain or shine; a cancelled event will not have a makeup date. Visit the organization's website for the most recent information.

Race information

20 mi
20 Miles
3 mi
3.33 Miles
Visit the organization's website for the most recent information.
Trail runs nearby

Run the Land and Lakes Relay, a scenic team race from Warren Wilson to Fonta Flora Brewery near Lake James. Teams of 4 or 6 run legs from 2.7 to 8.7 miles through scenic lakeside country, finishing at the brewery with a post race party.

Run the Catawba Falls 15k in Old Fort North Carolina, starting along the Catawba River before a rugged trail loop past waterfalls and creek crossings. Race proceeds support local conservation and the finish features food from nearby partner..

Run rugged, high country trails at the Mount Mitchell Heartbreaker in Old Fort, NC, choosing a tough 50 mile or 55 kilometer course with technical singletrack and big climbs. Enjoy scenic views, solid aid and rustic Camp Grier vibes.

Run the Seven Sisters 25 km in Montreat NC, a rugged mountain trail with about 4,000 ft of climbing and mostly singletrack through dramatic ridges and overlooks. Expect steep, technical terrain and a cupless format so bring your own water.