If you like a challenge, you’re in the right place. Pretty much every weekend in the Northeast, you can find an event somewhere to challenge yourself, whether it’s a 5K, triathlon, marathon, kayak race, bike race or something else.

But some people crave more than the average race. They seek out challenges that will push them to the edge of what they’re capable of – and not just physically, but mentally as well. Events where completion isn’t guaranteed, and, in many cases, is highly unlikely.

Thanks to our region’s diverse, challenging terrain – and the twisted, sadistic minds of a few race directors – the Northeast is home to some truly epic challenges. Our region boasts some of the toughest events you’ll find anywhere; races that test participants like few recreational experiences can.

Think you have what it takes to tackle one of these elite challenges? Here, in no particular order, are a few of the hardest events you’ll find in the Northeast.


In the world of sufferfests, the Peak Death Race is the event by which all other events are measured. Grueling and unpredictable, participants must perform a series of insanely difficult tasks over roughly three days with almost no sleep. They aren’t told what the tasks are ahead of time (tasks have included 12 hours of continuous barbed wire crawls and 3,000 burpees). Racers aren’t even sure exactly when the race will start or when it will end. One year, racers attended a mandatory meeting the evening before the race was scheduled to start in the morning. When they got there, they were told the race was beginning immediately. How’s that for unpredictability?


Untamed New England is the premiere adventure race in the Northeast. This non-stop race gives teams up to four days to complete a rugged course across more than 250 miles of wilderness. Teams use topographic maps showing “checkpoints” that must be visited in sequence. They progress from one checkpoint to another by hiking, paddling, mountain biking, orienteering, and more. The precise route a team travels between checkpoints is largely up to each team, making this a significant strategic challenge as well as a physical one. Traditionally held in Maine, the race moved to New Hampshire last year. No word yet on plans for this year.


Often referred to as “the Mount Everest of ultramarathons,” the Self-Transcendence 3100-Mile Race is the longest certified foot race in the world. Instead of taking place on wilderness trails like most other ultras, this race challenges runners to circle the same short route around one city block in Queens, New York for up to 52 days. Not only must runners average roughly 60 miles a day for nearly two months, they also must endure the mental challenge of running 5,649 laps in the same scenery. (Listen to a recent podcast about the Self-Transcendence 3100-Mile Race from Outside Magazine.)


In Europe, where cycling is a major sport, they tend not to give much thought to cycling events in America. But even most European cycling fans consider New Hampshire’s Mount Washington Bicycle Hill Climb to be the toughest cycling hill climb in the world. The climb along the Mount Washington Auto Road is 7.6 miles long. It has an average grade of 12 percent, with extended sections of 18 percent and a final 50 yards with a punishing 22 percent.

Cyclists take on the Mount Washington Hill Climb. (Mount Washington Auto Road Photo)

PEAK BLOODROOT 100 – Vermont

The Peak Bloodroot 100 isn’t your typical 100-mile ultra. Killer elevation and hellish terrain make this one of the toughest 100-mile races in the country. Racers tackle 10-mile loops over Pittsfield, Vermont’s mountainous terrain. Those who completed the race last year climbed more than 25,000 feet of elevation – that’s approaching Mount Everest territory. Race directors view trails as strictly optional, often having racers veer off-trail to push through thick woods, patches of thorns and rocky stream beds. If 100 miles seems too much, you can also try their 50-, 30- and 10-mile versions of the race. If 100 isn’t enough, some years they hold a 500-mile version.


This grueling, single-day pentathlon held each spring challenges participants to run, kayak, bike, hike and either ski or snowboard at various stages of the race. The Inferno begins with an 8.3-mile run that features 600 feet of climbing. Competitors then kayak 5.5 miles of whitewater followed by an18.2-mile bike leg that includes roughly 2,000 feet of climbing. Racers then hike roughly three miles of difficult terrain with more than 2,200 feet of climbing before finishing the Inferno by skiing or snowboarding a giant slalom course on the Northeast’s most iconic slope – Tuckerman Ravine. Participants can take on the course by themselves, or they can do it as part of a relay team.

A skier races down Tuckerman Ravine during the Tuckerman Inferno. (Friends of Tuckerman Ravine/Facebook Photo)

EASTERN STATES 100 – Pennsylvania

One of the most challenging 100-milers in the country, the Eastern States 100 is a 103-mile single loop trail that begins and ends at Pennsylvania’s scenic Little Pine State Park. The course features a total elevation gain of more than 20,000 feet, and it has a strict 36-hour cutoff. It’s also a qualifier for the iconic Western States 100.


If you want to test your paddling endurance, take on New York’s General Clinton Canoe Race. Held each May, the world’s longest single-day flat water canoe race attracts paddlers from around the globe and challenges them with a 70-mile course along the scenic Susquehanna River. While the challenge must be completed in a single day, the overall regatta is more like a paddling festival that takes place over several days and features challenges for all paddling levels.

Paddlers begin the General Clinton Canoe Race. (General Clinton Canoe Race/Facebook Photo)

INFINITUS 888K – Vermont

Each June, the Endurance Society holds a variety of rugged trail races in Brandon, Vermont, where their 100-mile race option is one of the shorter distances. While they offer race distances such as an 8-miler, a marathon and an 88K, they also offer a 250-miler and a deca-marathon, which is 10 marathons in 10 days. While that probably sounds challenging enough, their top event is an 888K in which racers must complete more than 500 miles in under the strict 240-hour cutoff. Understandably, this race has only had four finishers.


Compared with some of the other races on this list, New York’s Escarpment Trail Run might seem tame. After all, it is only 18 miles. But what it lacks in distance, it more than makes up for in horrifying terrain and a tight 6-hour cut-off. This single track trail in the northern Catskils crosses no roads and has total elevation changes of nearly 10,000 feet. It is extremely rocky and a runner must expect to navigate over boulders, downed trees, gullies and hidden roots the entire distance. Racers are warned to be prepared to deal with bees (yes, bees), slippery rocks, porcupines, black bears and anything else that can be found in the forests of the Catskills. In many places, runners must climb hand-over-fist to scale a rise. There are sections of the course that travel along cliffs, and racers are cautioned that if they’re not careful, they could fall to their death. Sounds fun, right?

Think there’s a race that we missed? Let us know what you think belongs on this list.