We profiled five top St. Louis-area trail races in our very first issue back in 2014. It seemed fitting, therefore, that we circle back on the off-road offshoot of pavement pounding to see how things have changed (or not) in the last decade. We talked to a number of local experts and also drew from five years of Terrain Magazine Readers’ Choice Awards, landing on 10 trail races that distinguish themselves through course, format, or seasonal conditions.

Alpine Shop Trail Run Series
Distance: ~4 miles
Date: Thursday evenings in August
Location: Queeny Park (Ballwin, Mo.)
For trail runners in St. Louis, Thursday nights are the highlight of August. For four weeks in a row, runners young and old gather after work at Queeny Park to conquer 3 to 4.5 miles of mixed-surface trail. The route is different each time, and the heat and hills make every outing a mini adventure. Afterward, the grilled hot dogs, cold beer, music, and giveaways make it a party. The Alpine Shop Trail Run Series is friendly to families and folks of all skill levels. offroadracingleague.com/trail-run-series/

The Skippo
Distance: 10k, half marathon, 30k, 40k Challenge
Date: November 9-10
Location: Castlewood State Park (Ballwin, Mo.)
This Skippo was named after local running legend Skip MacDowell, who has volunteered countless hours maintaining the trails on which it takes place. The race began in 2009 as a 20k that featured two loops on a fairly flat course — except, of course, for the notorious wood stairs. It was at MacDowell’s urging that other distances were added to involve as many runners as possible, turning it into a weekend event. Tackle the 10k on Saturday and the 30k on Sunday to complete the 40k Challenge. bigrivertrailseries.com/the-skippo/

Devil’s Toll Race
Distance: Half marathon
Date: October 12
Location: Ozark Trail (Middle Brook, Mo.)
It’s hard to beat this race for significant backdrops. In just over 13 miles, runners traverse Taum Sauk Mountain (the highest point in Missouri), scenic Mina Sauk Falls, the Devil’s Toll Gate rock formation, and Johnson Shut-Ins State Park and its infamous Scour Trail before crossing the Black River to finish. Just when you think you’ve hit your stride, prepare for another hill, techy section, or twist in the trail. Participants can opt for the running race or the hiking race, solo or as part of a two-person team. ultrasignup.com

The Devil’s Toll Race. (Ozark Trail Association)

Pere Marquette Endurance Run
Distance: 7.8 miles
Date: December
Location: Pere Marquette State Park (Grafton, Ill.)
Don’t let the distance fool you; this is pound-for-pound one of the toughest trail races in the region. That reputation comes mainly from a course that’s known for continuous, steep elevation changes, climbing hill after hill during the race, with a demoralizing “stone staircase” that can reduce winners to whiners. Add in the unpredictable Midwest winter weather — the race has been run in freezing rain, snow, and inches of thick mud — and you have the formula for one grueling event. thedriven.net/cs/metrotriclub/

Run the Leadbelt
Distance: 3 mile, 8 mile
Date: July 13
Location: St. Joe State Park (Park Hills, Mo.)
Part of a weekend that also includes a big mountain bike race, Run the Leadbelt is ideal for beginners wanting to branch out with an out-of-town event. The distances are accessible, with a both a 5-mile and 1-mile option, and the trails are buffed in preparation. The routes wind through a mix of hardwood forest, open savannah, creek crossings — even a corrugated metal culvert pipe. New this year is the addition of a half-marathon option, allowing athletes who choose to trail run and mountain bike during the weekend to prove they are “miner though.” facebook.com/Leadbeltracing/

Quivering Quads Trail Race
Distance: 9 mile, half marathon
Date: March
Location: Cuivre River State Park (Troy, Mo.)
Keeping a race fresh for 25 runnings can be hard. Quivering Quads has stayed on top of its game by sticking with what works — every edition has been held at Cuivre River State Park — and reimagining the rest. That means periodically subtracting and adding distances, rerouting the course, and giving participants a choice of swag options rather than dictating one. What runners can always expect is a race with amazing scenery on a variety of fire roads, singletrack, and rolling hills. fleetfeet.com/s/stlouis/qq

Ozark Foothills Endurance Runs
Distance: 25k, marathon, 50k, 50 mile, 100k, 100 mile
Date: April 6-7
Location: Greensfelder County Park (Wildwood, Mo.)
There are trail runners, and there are ultra runners. (If you have to ask, you’re in the first group.) Ozark Foothills caters to both by offering a half-dozen distances: 50k and up on Saturday; 25k and marathon on Sunday. As you’d expect from its name, the race takes place on transitional terrain ranging from scrappy climbs and rock gardens to flowy singletrack and lowland forest. A cool option: The 50k night race starting at 9 p.m. on Saturday lets you run the route in the dark. terraintrailrunners.com/ozark-foothills.html

Corps of Discovery Half Marathon
Distance: 5 mile, half marathon
Date: August 31
Location: Lewis & Clark Trail (Weldon Spring, Mo.)
St. Louis Track Club launched this race in 2013, and since then, the half marathon has grown to be one of the most popular in the region. Held on Lewis & Clark Trail the run has some steep climbs and descents, narrow switchbacks, and scenic overlooks of the Missouri River. This race is ideal for the intermediate off-road runner who wants a doable distance that won’t take all day, held on a challenging trail. stlouistrackclub.com/corps-of-discovery

Castlewood Cup 15K Trail Race
Distance: 15k
Date: February 3
Location: Castlewood State Park (Ballwin, Mo.)
Set in one of St. Louis’ most popular parks, Castlewood Cup winds through flat bottomland, up rocky hillsides, and along bluffs overlooking the meandering Meramec River. Winter conditions can play a part, so much so that there are even “fair weather” and “ice/snow” routes that will be decided on the week of the event. Stick around for the post-race party that includes great BBQ, snacks, and beer from Urban Chestnut Brewing Company. bigrivertrailseries.com/castlewoodcup/

KT82 Trail Relay
Distance: 82 miles
Date: June
Location: Katy Trail State Park (Maryland Heights to Hermann, Mo.)
The least traditional race on our list, the KT82 is like a daylong running road trip. You and five others (two if you choose the ultra option) jam into one vehicle and trade off to complete 18 legs and 82 linear miles on the crushed limestone Katy Trail. (Four of the legs involve more challenging singletrack on St. Charles County trails.) Imagine quirky team names, matching costumes, decorated vans, scenic views, and charming towns. You might want to stay the night and enjoy the local wineries in Hermann before heading home the next day. gostlouis.org/kt82

Author: Brad Kovach is the editor/publisher of Terrain Magazine. Additional reporting for this story provided by Stephanie Zeilenga and Mike Mehan.
Top Image: The Skippo at Castlewood State Park.