UltraRunning Magazine Presents: Old School Ultras – Class of 2026

There’s a certain kind of race that built this sport — no frills, no hype machines, just honest miles, rugged terrain, and the kind of community that remembers your name at the finish line. Old School Ultras – Class of 2026 celebrates the events that helped shape ultrarunning into what it is today.

These are the grassroots races. The ones that existed before lotteries were trendy. The ones run by passionate trail stewards and local legends. The ones where buckle earners, first-timers, and decades-deep veterans all share the same course.

If you’re looking for authentic ultrarunning — this is your list.

What “Old School” Means

  • Runner-focused, community-driven events
  • Thoughtfully challenging courses with real terrain
  • Longstanding race traditions and history
  • Dedicated volunteers and experienced race directors
  • A welcoming vibe for both first-timers and seasoned ultrarunners

These races don’t need flash. They’ve earned their reputation mile by mile.

2026 Old School Ultras

Stump Jump
Stump Jump
Register: UltraSignup
Premier Southeast 50K and 10 Miler featuring 90% singletrack, Tennessee River Gorge views, and 25 years of trail tradition.
Grasslands Trail Run
Grasslands Trail Run
Register: UltraSignup
Wide-open prairie miles and classic endurance grit.
Syllamo’s Revenge 3 Days of Syllamo
Syllamo’s Revenge 3 Days of Syllamo
Register: UltraSignup
A rugged multi-day challenge built for runners who love climbing and technical trails.
Mad City Ultras
Mad City Ultras
Website: Official Site
Urban-meets-trail endurance with Midwest heart and community energy.
McDonald Forest Trail Run
McDonald Forest Trail Run
Register: UltraSignup
One of Oregon’s oldest ultras, “The Mac” delivers 30 years of forest singletrack, McCulloch Peak climbing, and a signature pine-needle downhill finish.
Silver State 50/50
Silver State 50/50
Register: UltraSignup
High-desert beauty with serious climbing and Nevada grit.

 

Kettle Moraine 100
Kettle Moraine 100
Register: UltraSignup
A storied Midwest hundred with deep roots and legendary buckle history.
Knee Knackering North Shore Trail Run
Knee Knackering North Shore Trail Run
Website: Official Site
Iconic mountain terrain and a reputation for toughness.
Skyline 50K
Skyline 50K
Register: UltraSignup
Elevated views, sustained climbs, and rewarding miles.
Baker Trail Ultra Challenge
Baker Trail Ultra Challenge
Register: UltraSignup
A 50-mile point-to-point ultra on the historic Baker Trail featuring road-to-woods terrain, navigational focus, and a unique three-part finisher medal series.
TARC Stone Cat Trail Festival
TARC Stone Cat Trail Festival
Website: Official Site
New England trail tradition with community at its core.

Old School Alumni

Mountain Mist 50K Trail Run
Mountain Mist 50K Trail Run
UltraSignup
Chuckanut 50K
Chuckanut 50K
Official Site
Crown King Scramble
Crown King Scramble
UltraSignup
Peterson Ridge Rumble
Peterson Ridge Rumble
UltraSignup
Strolling Jim
Strolling Jim
UltraSignup
MIWOK 100K
MIWOK 100K
Official Site
Ice Age Trail 50
Ice Age Trail 50
Official Site

 

Diez Vista 50K
Diez Vista 50K
Official Site
Laurel Highlands Ultra
Laurel Highlands Ultra
UltraSignup
Vermont 100
Vermont 100
Official Site
Cascade Crest 100 Mile
Cascade Crest 100 Mile
UltraSignup
Waldo Trail Run
Waldo Trail Run
UltraSignup
Tamalpa Headlands 50K
Tamalpa Headlands 50K
UltraSignup

 

The Plain 100
The Plain 100
UltraSignup
Man Against Horse Race
Man Against Horse Race
UltraSignup
Pine Mountain Trail Run
Pine Mountain Trail Run
UltraSignup

 

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