Orienteering isn’t just physical. The sport puts one’s mind to the test along with one’s muscles. While crossing rugged, sometimes dangerous terrain, an orienteer must make hundreds of decisions and scrutinize every topographic line on the map. The most adventurous orienteering courses demand that racers compete on mountain bikes, in cars, on foot and on skis. From the insane alleycat races of New York’s back streets to the endurance fests of the Scottish Highlands, these are five of the toughest challenges orienteers will find in organized competition.

Monster Track 

Alleycat races are the urban cousins of mountain bike orienteering. Instead of winding trails and mountain landscapes, alleycat practitioners choose city streets as their courses, which present the same navigational challenges as orienteering anywhere else, only with scads of nutty cab drivers to outspeed and avoid. The Monster track is one of the premier races in New York — one of the best cities in the world for urban cycle culture. Like most alleycats, Monster Track is unsanctioned; it’s basically illegal, as well as dangerous and downright insane. There are no traffic blocks and no corporate sponsors — only racers darting through New York streets, battling for respect. In Monster Track, the Best Crash prize is among the most coveted. Oh yeah, brakes are disallowed, too.

The World Ski Orienteering Championships

Ski Orienteering is for athletes who aren’t challenged enough by the lung-busting rigors of cross country. Ski orienteers were not content with the sport until it adopted maps, compasses and soft, narrow tracks, which are much more strenuous to ski down than the hard, groomed trails regular Nordic skiers use. The World Ski Orienteering Championships is held every other year, often in northern Europe. Racers have to make hundreds of decisions to reach the course’s checkpoints in the correct order, a feat as mentally demanding as the race is physically. And if the sport seems unfamiliar now, it won’t soon: it was a recent addition to the Olympic Games.

World Rogaining Championship

The bizarrely named World Rogaining Championship has nothing to do with growing hair. Except that hair will sprout on chests of survivors of this 24-hour adventure race in the Australian outback. The odd name doesn’t come from the character-building effects of venturing into the Australian bush armed only with a map, but from the names of the sport’s founders. Modern orienteering challenges owe this granddaddy some gratitude: it has been around since the 1940s, when teams of two to five people began venturing into the bush to compete. Longer versions do exist (they are called Endurogaine) and today the race is held in a different country every time. Rogaining attracts talented orienteers, because the object is to find as many checkpoints as possible as fast as possible.

Lowe Alpine Mountain Marathon

The sport of fell running is the old tradition of running through the highlands of Northern Britain, often for days at a time carrying the necessary food and shelter. It is the picture of pure adventure: a pair of running shoes and a map are the only pieces of gear participants need. The Lowe Alpine Mountain Marathon in the Scottish Highlands is descended from this tradition. Since it was founded in 1994, it has been seen as a wilder, more rugged version of the older events of its kind. The location is kept secret until racers are given a list of checkpoints to navigate between. Along the way they traverse craggy cliff sides, scramble through rocky gorges, sprint up steep hillsides and wade (quickly) through bogs.

Lionheart Adventure Race

The rugged landscape of Western Pennsylvania is home to the one and only Lionheart Adventure Race. The course, which traverses 90 miles through Ohiopyle State Park, is the ultimate test for orienteers and outdoor adventurers. In addition to the map and compass skills and quick thinking that characterize all orienteering challenges, Lionheart thickens the plot by testing competitors with an array of adventure techniques. Mountain biking, kayaking, rappelling and trekking are all needed to finish the course. It is “one of the best endorphin fixes of your life,” according the race’s website.