Obstacle Wonderland's Rise of the Obstacles 5K

Wallkill, United States • 30-31 May 2026

Rise of the Obstacles : Obstacle Wonderland, Wallkill NY (May 30-31, 2026)

Rise of the Obstacles is a two-day outdoor obstacle course event at Obstacle Wonderland in Wallkill, NY. The event offers separate days for kids and adults and provides access to permanent outdoor rigs, field obstacles, and trail sections.

Event formats and distances include:

  • Adults: Crown of Fire 100 m sprint
  • Adults: Dragon Slayer multi-lap endurance course (laps include trail and rig sections)
  • Kids: Fire Breather 50 m sprint
  • Kids: First Roar 1 km endurance course

The Crown of Fire 100 m is a lane-style obstacle sprint with dense obstacle placement and two timed attempts; the fastest time counts. The Dragon Slayer endurance format uses repeated laps with multiple passes through rigs and trail sections; strength and grip fatigue build with each lap. Kids events include competitive sprints and a non-competitive 1 km course with kid-friendly obstacles; children under six may run with parent assistance and will not be timed. Age-group awards and finisher medals are provided for most heats.

Additional on-site elements include a nonprofit Teddy Bear Crawl presence that supports hospital-bound children and an on-site 3D printing fundraiser for youth programs. The event is fully outdoor; organizers will monitor conditions and make announcements if weather creates unsafe conditions. Portable restrooms and event parking are provided on-site. Visit the organization's website for the most recent information.

Race information

Adults "dragon Slayer" Endurance Obstacle Course
Adults "crown of Fire" 100 Meter Sprint Ocr
Kids "fire Breather" 50 Meter Sprint Ocr
Kids "first Roar" 1k Ocr
Visit the organization's website for the most recent information.
Trail runs nearby

Experience a 5K cross country run or walk through the mowed trails of Peach Hill Park. Reach the highest point in Poughkeepsie for panoramic views and enjoy post race snacks and awards.

An 8.6 mile trail run at Minnewaska State Park Preserve on June 24 with chip timing and commemorative towels for finishers. Entry is limited to 250 runners and parking carries a 10 USD per car fee.

The Red Wing Trail Challenge in Lagrangeville, NY on July 5, 2026 offers 60K, 30K and 15K trail races with substantial elevation gain. The event includes aid stations, an interactive course map, on course fuel and post race food and drinks.

Experience a midweek evening trail run through the diverse terrain of Bowdoin Park. This 5 mile race features a mix of grass and rocky trails with awards for top finishers and a food drive for the local pantry.

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