Matthew Shepard

courtesy of Matthew Shepard

Crowsnest Pass, Alta., has a new claim to fame: the Crowsnest High Five, a challenge dreamed up by Alberta runner Matthew Shepard that links five of the region’s best-known mountains: Turtle, Coulthard, Crowsnest, Tecumseh and Bluff. Participants can tackle the peaks in a single push or over several outings, tracking their progress along the way.

Matt Shepard
Matt Shepard, High Five FKT 2025. Photo courtesy of Matt Shepard

Shepard, known locally as “Shep,” was the first to complete the full route at the end of September, finishing in 26 hours, 46 minutes and five seconds to establish the inaugural Fastest Known Time (FKT). “I had wanted to do something big and iconic in CNP with similar vibes as the Canmore Quad,” Shepard told Canadian Running. “This area has such a beautiful network of trails and some really prominent peaks that beg for an adventure.”

From solo effort to community challenge

Shepard’s idea began as a personal endurance goal, but quickly evolved into a community challenge after his run captured local attention. “I arrived at the Coulthard summit just before sunrise, so that was a pretty special moment to kick off the adventure,” he said.

During the attempt, Shepard hit a rough patch on Turtle Mountain, where a bout of nausea and a tough scramble slowed him down. “I crashed and burned on the scramble between the false and true summits,” he said. “Luckily, I had great support from my friends Kyle Ross and Skylar Roth-MacDonald. They pushed me through that segment in about five hours, much slower than I had intended. “The high point came atop Crowsnest Mountain. For all the time I’ve spent exploring the region, I hadn’t been to that summit. Once I hit it, I felt confident I could finish under my estimated time.”

 

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How to take on the High Five

The Crowsnest High Five challenge is open to hikers, runners and anyone looking for a big adventure. There are two ways to complete it.

Standard route: Start and finish at the same point, summiting all five peaks in one continuous push.

Peaks only: Summit each of the five mountains individually, starting and finishing at each trailhead. You can spread it out over multiple outings, or a full season.

High-five challenge
High-five challenge. 2025. Photo courtesy of Matthew Shepard

To make it official, pick up a commemorative High Five deck of cards from Spry, an outdoor activewear store in Blairmore, Alta., or online at spryactive.ca. Each summit has an orienteering punch hidden in its register—use it to stamp your card. Once you’ve collected all five, bring your card back to Spry to unlock finisher’s merchandise and join the growing list of High Five completers.