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I’m going to assume that you’re asking about real running events, and not mud races. The first criteria for a quirky, fun event is that it has to be one-of-a-kind. A race series that’s organized by some for-profit company in multiple cities across the country is automatically disqualified for being too antiseptic. Locally-based races, on the other hand, usually take full advantage of the hometown scenery and vibe, are embraced by the area running community, and generally benefit a specific charity that’s meaningful to the people there. The second criteria is that it has to make your friends jealous when they hear you’re running it. These five races top the list.
The Sandmine Challenge
Location: Crystal City, Missouri
Distance: 3-plus miles
Most recent winning time: 17:42
Dark, dank, and perpetually 56 degrees, the course for the Sandmine Challenge in Missouri is like no other in the country. As its name implies, its meanders entirely underground through an old sand mine, so the footing is always soft, uneven and puddle-filled. Don’t forget a headlamp and thick gloves for climbing over obstacles.
Krispy Kreme Challenge
Location: Raleigh, North Carolina
Distance: 5 miles
Most recent winning time: 30:07
The granddaddy of quirky races is the Krispy Kreme Challenge in Raleigh. Course description: Start on the North Carolina State University campus, run 2.5 miles to a Krispy Kreme shop where you eat one dozen doughnuts, then run 2.5 miles back to the start. It originated as a college dare a decade ago, and now receives more than 2,000 entrants at the start line each February. Along similar lines, there’s also an annual Twinkie run in Ann Arbor, Michigan, and Hot Dog Challenge in New York City.
Damon Runyon 5K
Location: Yankee Stadium, Bronx, New York
Distance: 5 kilometers
Most recent winning time: 18:48
This is the baseball race of dreams, held every August entirely within Yankee Stadium. Runners wind their way up and down the stadium’s concourses and stairs, and can catch a glimpse of themselves on the jumbo screen above the center field bleachers as they follow the course along the warning track.
Night of the Running Dead
Location: Sandy, Utah
Distance: 5 kilometers
Most recent winning time: 15:25
This Halloween-themed event held in mid-October has a creative twist: runners not in costume enter in the “human” division and start running at 9 p.m. (in the dark, of course). Runners dressed in zombie costumes are placed in the “undead” division and start two minutes later, so they can chase the humans.
Kona Underpants Run
Location: Kona, Hawaii
Distance: 1.2 miles
Most recent winning time: Not relevant
This race isn’t about time, it’s about a simple statement: “Put some clothes on!” It was started by a few local athletes in 1998 as a funny way to tell visiting competitors in the Ironman World Championships to stop wearing their Speedos into local banks, restaurants, and grocery stores. Now hundreds of people—natives and visitors alike—line up during Ironman week in their underthings to jog the 1.2-mile course and raise money for local charities.