Elena Friedman always looks forward to a signature element of The Skippo trail race: the stairs.

“It’s fun to count how many there are, and I always lose track by the top,” said Friedman, a certified athletic trainer who participates in the event each year.

But even if she can’t quite keep count of the steps — there are 205— she doesn’t forget the scene at the top.

“The reward is you get to see the beautiful bluffs,” she said of the event at Castlewood State Park.

That sequence is one of the reasons why Terrain Magazine readers selected both The Skippo and its sibling race, Castlewood Cup, for a 2018 Readers’ Choice Award. (The latter race is known for its creek crossing and a charge up Cardiac Hill.)

Big River Running Company launched the two trail races in 2009 because owner Matt Helbig wanted to provide runners alternatives to the more common road races, he said. And the only local trail race he knew of was the Pere Marquette Trail Run at the state park in Grafton, Illinois.

“A lot of folks who have done the half-marathon and marathon scene are kind of looking for that next challenge, and that’s where trail running comes in,” Helbig said. “It’s a little easier on the body, and it’s just a nice change of pace from logging miles on the roads.”

The events now typically sell out, with a maximum of 500 runners allowed at the park each day.

Some of that interest has to do with the location.

“Castlewood is hands down the best venue in St. Louis,” Helbig said of the area along the Meramec River. “One, it’s in close proximity to where a lot of trail runners live, and two, you just can’t beat the trails.”

The Skippo, held each November, acts as a good bookend for some, marking the end of the running season. The event was originally just a 20K, but at the urging of Skip “Skippo” MacDowell, the legendary volunteer who helps maintain Castlewood’s trails, Helbig added 10K and 30K options.

At the other end of the calendar in February, Castlewood Cup helps runners ease out of winter with a 15K race.

In organizing the events, Helbig tries to offer a quality collection of extras. At Castlewood Cup, participants receive a hooded sweatshirt. At the Skippo, there is the coffee mug. And there are different medallions for each race, depending on the distance.

“We’ve been giving out mugs since the first year, and everyone has a collection of Skippo mugs in their cabinet and are drinking their coffee out of them every morning,” said Helbig.

After the races, runners can chow down on barbeque, sip beers and listen to music.

Helbig explained, “With our events, we try to do all the little things well, and all the little things add up to a big event.”

Author: Eric Berger is a contributor to Terrain Magazine