5 Steep Trail Running Routes Worth the Challenge

If you love trail running for the views, the fresh air, and the challenge, you will really love these steep routes. Whether you’re already trained up for the elevation change, or looking to up your game, test yourself on one of these iconic routes in key spots across the country. Find even more great routes for every fitness level in this comprehensive guide, and wherever the trail takes you and whatever conditions you encounter, take on any terrain with the Brooks Cascadia Collection—and experience the force of nature.

Longs Peak, Rocky Mountain National Park, Colorado

13.6 miles

Yes, 14,259-foot Longs Peak is the tallest mountain in Colorado, but that’s not why it’s such a magnet for ambitious trail runners. It’s because the challenging route delivers the perfect balance between smooth-striding singletrack and rocky, test-yourself scrambling. Caution: The last mile is an exposed, rocky scramble.

Mission Trails Five-Peak Challenge, San Diego, California

16.3 miles

The precise distance of this run depends on the route you choose, but one thing doesn’t change: the epic views of ocean and peaks and valleys. The classic challenge strings together the five peaks in Mission Trails Regional Park: Cowles Mountain, Pyles Peak, Kwaay Paay, and North/South Fortuna. It’s an epic day with more than 4,000 feet of climbing. Just pack plenty of water for the dry terrain.

Art Loeb Trail, Canton/Davidson, North Carolina

29.4 miles

Put all of North Carolina’s forest highlights together on the Art Loeb Trail, affectionately known as one of the toughest trails in the East. The route climbs more than 8,000 feet, descends nearly as much, and traverses wildflower-filled ridgelines and travels up and over big-view balds in the Pisgah National Forest. It’s such an iconic one-way route that local shuttle services have sprung up, making logistics easy.

The Enchantments Thru-Run, Leavenworth, Washington

18.6 miles

You’ll want to keep your phone handy for nonstop photos on this breathtaking route. The point-to-point epic serves up granite slabs, alpine lakes, rocky spires, creek crossings, and (often) mountain goats in the Alpine Lakes Wilderness. The run can be tackled in either direction, but the most popular—west to east—delivers a whopping 2,200 feet of climbing in a single mile up Aasgard Pass (the whole route climbs more than 5,000 feet). Local shuttle services are available.

Rim-to-Rim-to-Rim (or Rim-to-River), Grand Canyon

40.6 miles

When it comes to big-adventure trail runs, nothing compares to crossing the Grand Canyon. There’s also nothing steeper (it packs in more than 22,000 feet of elevation change), so get fit and get equipped. From the South Rim, you plunge to the Colorado River on the South Kaibab Trail, ascend to the North Rim on the North Kaibab Trail, and reverse course. The payoff: the run of a lifetime.

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