Top 5 Endurance Challenges Every Endurance Athlete Should Try

As an endurance athlete, the last few years have taken me from luxury Everesting weekends to raw, self‑supported days deep in the Grand Canyon, and each endurance challenge has changed me in a different way. I’ve stood on every one of these start lines, 29029 Everesting, Elevation Everest, UltraTrax, MammothMarch, and Grand Canyon Rim‑to‑Rim, felt the highs, hit the lows, and learned what it really takes to keep moving when quitting sounds easier. Being an endurance athlete is about far more than race day; it’s about the day‑in, day‑out process of training, dialing in your fueling and hydration strategy, and figuring out exactly what to wear and which gear you trust when things get uncomfortable. When you learn to enjoy that full journey, every endurance challenge stops being just an event on the calendar and becomes a powerful tool for growth, grit, and transformation.

Top 5 Endurance Challenges in the US and Canada

In 2026, my calendar isn’t built around holidays or long weekends, it’s built around training for endurance challenges that each demand a different version of my best. These endurance events blend massive elevation gain, long days on your feet, and serious mental tests, making them ideal proving grounds for any endurance athlete looking for their next big goal.

This guide walks through my top 5 endurance challenges in the United States and Canada, why each one is special, and what kind of endurance athlete might love (or fear) them most. If you’re searching for your next endurance challenge, whether mountain, trail, or canyon, this list will give you real‑world context, not just glossy marketing promises.

29029 Everesting – The Endurance Challenge that Cares the Most!

29029 Everesting is where the Everest metaphor becomes real: you have 36 hours to climb 29,029 vertical feet, the height of Mt. Everest, by hiking up a ski mountain and riding the gondola down, over and over. The organizers rent a private mountain and build an all‑inclusive basecamp with food, drink, recovery, and community, so the entire endurance challenge feels like a cross between a mountain festival and a personal transformation retreat.

This was my first entry into the world of endurance challenges, and it did not go the way the highlight reels suggest. I signed up for the Snowbasin, Utah event in 2022, and it completely crushed my soul, I fainted before lunch, and my wife spent the night in the hospital, a painful reminder that even the best‑supported endurance event demands serious respect and preparation. That “failure” became the spark for a deeper journey as an endurance athlete to figure out training, fueling, hydration, and mindset so I could come back stronger, and yes, I signed up to do it again and again and again and again.

What makes 29029 unique as an endurance challenge is how supported 29029 makes you feel. Your entry includes a five-month training program plus access to coaches, nutrition and mindset guidance, lodging, and all the food and drink you need during the event, so you’re supported from registration to completion (Red Hat). On event weekend, some locations feature glamping tents at basecamp while others partner with world‑class resorts, which turns a brutally hard endurance challenge into something that still feels friendly, intentional, and surprisingly comfortable between laps. If you have never participated in an endurance challenge and do not know where to start, I highly recommend 29029 because they take the guesswork away from you. You get a proven plan and support designed to set you up for success. This event has been called “frustratingly doable”. It is hard no matter which mountain you go to but 29029 does everything it can to help you get up that mountain and even has on mountain coaches that have a way of finding you when you most need it.

I have climbed in this event four times. Snowbasin 2022 (No Red Hat), Snowbasin 2023 (No Red Hat), Stratton 2023 (1^st Red Hat) and Whistler 2025 (2^nd Red Hat). This year I am part of the 2026 Kyle Pease Foundation 29029 Mont Tremblant team. I can’t wait to climb this mountain. 1) I am raising $11,000 for disabled athletes. Consider donating at this link: KPF Fundraiser; 2) My wife and two children will be there volunteering and 3) I will know at least 25 other climbers.

2. Elevation Everest – Relay‑friendly Endurance Challenge at Altitude

Elevation Everest takes the Everesting concept to Colorado’s Winter Park Resort and turns it into a lap‑based endurance challenge focused on elevation gain. Each lap is roughly 1,600 feet of vertical and about 2.2 miles, and athletes hike or run up, then ride the gondola back down to reset before the next climb.

For an endurance athlete looking for a more approachable Everesting‑style challenge, the relay format is a game‑changer. You can race solo or create a team of two, three, or four, sharing laps and encouraging each other instead of carrying the entire workload alone, which makes this endurance challenge a great entry point for newer athletes or friends tackling a big goal together. In September, the golden aspen trees at Winter Park create a stunning backdrop, which makes the hard work feel just a little more magical as you grind out vertical gain at altitude.

One of the best parts of Elevation Everest is Base Camp, where saunas, cold plunges, DJs, yoga, and recovery zones keep energy high between laps. The event intentionally builds community around the endurance challenge, and past athletes describe the experience as spending a weekend with family and friends, all working toward remarkable goals on the same mountain.

I tried to solo climb this event in 2025 and elevation and I are not good friends. I made it halfway, covering five of the 10 laps needed for a Half Everest medal. It was an amazing experience as I was blown away by the professional athletes who were literally running up the mountain. And 2 participants did 20 laps, which was a Full Everest…. 29,029 feet of elevation in 17 hours! This effort was beyond impressive. I am hoping that 2026 brings me back to Winter Park where I can try this event again as part of a relay. And maybe one day I will try to complete all ten laps solo once again.  

3. UltraTrax Bear Creek – The Choose Your Own Distance Endurance Challenge

UltraTrax Bear Creek in Macungie, Pennsylvania is a one‑day endurance challenge built around loops, choice, and progression. The course is a roughly 7‑mile loop with about 1,200 feet of elevation gain per lap, and each endurance athlete can pick a distance goal of 7, 14, 21, or 28 miles, with up to 10 hours to finish.

What makes UltraTrax so useful for an endurance athlete is the ability to customize the challenge. You decide how many loops to attempt and whether to carry added weight in a ruck (10, 20, or 35 pounds) or hike unweighted, which lets you tailor the endurance challenge to your current fitness and upcoming goals. The route winds up, down, and around a Pennsylvania ski area, so the combination of climbs and descents quickly reveals how your legs, fueling, and hydration strategies hold up over multiple hours on rolling terrain.

With regular aid stations, a supportive lodge atmosphere, and a post‑event celebration, UltraTrax Bear Creek gives you the structure of an organized endurance event without the pressure of strict cutoffs or traditional racing. It’s an ideal endurance challenge to test gear, refine a hydration plan, and log serious time on your feet before bigger mountain events.

In 2025 my wife and I participated in this challenge as preparation for our Grand Canyon Rim 2 Rim crossing. We hiked 14 miles carrying 20 pounds of weight and we did it in the rain and mud so it was good practice hiking downhill in challenging conditions. I signed up to do this event again in 2026 and will be doing so with a group of 20 friends that will also be climbing in a 29029 challenge in 2026.

4. Mammoth March – Hiking Focused Endurance Challenge

Mammoth March bills itself as “the hiking challenge of your life,” and its events across the United States and Canada follow a simple formula: 20 miles in 8 hours. For an endurance athlete who prefers fast hiking over running, this endurance challenge is a perfect bridge between casual day hikes and more extreme ultras, with a clear time goal but no official timing chips or public “DNF” list.

Each Mammoth March route is designed to showcase scenic parks and trail systems, combining rolling terrain, aid stations, and big views to keep you engaged throughout the day. The format attracts a mix of experienced endurance athletes and newer hikers, creating a supportive on‑course environment where the primary competition is with the clock and your own pacing, not the people around you.

For training, Mammoth March is a powerful endurance challenge because it forces you to dial in sustainable pacing, nutrition, and hydration over a full day on your feet. By the time you finish 20 miles in under 8 hours, you’ve earned both a finisher medal and a meaningful boost in confidence for whatever endurance event comes next.

My wife and I did this event in 2023 in Maryland, and it was great practice with lots of time on your feet. The course was generally rolling hills with not too much technical footing. I signed up to hike in this event in 2026 and will be doing so with some friends that will also be participating in the 29029 Mont Tremblant event with me.

5. Grand Canyon Rim‑to‑Rim – Self‑supported Endurance Challenge with Real Consequences

If the first four are “supported” endurance events, Grand Canyon Rim‑to‑Rim is the raw, no‑frills endurance challenge that reminds you nature always has the final say. On paper, the route is simple: start on one rim, descend into the canyon, cross the inner corridor, and climb out to the opposite rim. In reality, this endurance challenge is a long, exposed push where heat, extreme elevation change, limited water access, and complicated rescue logistics can turn a big adventure into a serious survival scenario.

In 2025, the Grand Canyon was especially unforgiving. There were hiker fatalities and multiple rescues tied to heat, overexertion, and challenging trail conditions, even as the park worked through a major Transcanyon Waterline replacement project and managed fire activity near the North Rim that stressed water and access further. Those factors made the Rim‑to‑Rim endurance challenge even more serious for every endurance athlete attempting it.

My wife and I took on Rim‑to‑Rim in May 2025 with friends, and it was no joke. Two hikers in our group got sick, including my wife, and we spent an extra 27 hours at the Manzanita Rest Area because she was unable to walk, turning a planned one‑day endurance challenge into an unexpected overnight test of patience and resilience. In the middle of that, squirrels went after our PB&J sandwiches, mice chewed through socks, and the canyon made it painfully clear there are no aid stations, med tents, or cheering crowds; if you walk down, you must walk yourself out or wait a long time for help that may or may not come depending on the life and death nature of the circumstance and the danger posed to the rescue teams.

For the endurance athlete who wants a challenge that strips away all the extras, Grand Canyon Rim‑to‑Rim delivers a powerful reminder that preparation, humility, and respect for the environment are non‑negotiable.

Why These Endurance Challenges Belong on Your List

Together, these five endurance challenges create a full‑year curriculum for any endurance athlete. 29029 Everesting and Elevation Everest deliver big vertical gain with resort‑style support and community, making them ideal for athletes who want a high‑touch endurance challenge experience. UltraTrax Bear Creek and Mammoth March offer flexible, accessible endurance events that help you practice pacing, fueling, and hydration without overwhelming logistics or cutoffs.

Grand Canyon Rim‑to‑Rim is the wild card, the endurance challenge that strips away the banners, music, and basecamps and leaves you alone with your training, your mindset, and a canyon that does not negotiate. As an endurance athlete, rotating through challenges like these builds not just fitness, but identity: you become the kind of person who signs up, shows up, and keeps saying “yes” to the next big endurance challenge, no matter how steep, long, or uncertain the path ahead. I keep doing these events because I love the “new me” that emerges after one of these challenges. Keep climbing and go for One More Ascent!

If you want to learn more about Gavin Mlinar, check out my website: yesyourway.com.

And Don't forget to check out my book: Yes Your Way to Success! Why Don't You?

Click this link to Support the 2026 Kyle Pease Foundation 29029 Everesting team