19 Wild and Wacky Fun Runs

Gorilla Run, Photo: Hans Bucher, Courtesy of Gorilla Run

Let’s face it, sometimes even the most ardent runner needs to shake up the routine a little bit. A little variety never hurt anyone—in fact it’s a chance to experience something entirely new. We searched high and low for the nation’s most peculiar yet challenging fun runs. Here’s your chance to get off the beaten path in 2016.

The Empire State Building Run-Up

Feb. 3, New York City

Though you are only running less than a quarter-mile in this unique vertical sprint, your heart will be pounding and your lungs screaming by the end of it. That’s because you’ll be on top of the Empire State Building—a mere 1,576 steps, or 88 flights of stairs from the street-level starting line.

Krispy Kreme Challenge

Feb. 6, Raleigh, N.C.

What began among 10 friends over a decade ago now boasts more than 8,000 runners who run 2.5 miles from North Carolina State University into downtown Raleigh for a dozen glazed donuts from Krispy Kreme. Luckily you get to run another 2.5 miles back trying to keep them down.

Cupid’s Undie Run

Feb. 13–14, multiple locations

Every Valentine’s Day weekend, thousands of runners across the country strip down to their skivvies and run a mile to help raise money to fight neurofibromatosis, a rare children’s genetic disorder that occurs in 1 in every 3,000 births. The more you raise, the better the swag earned—post-race open bar, exclusive undies and socks and a stylin’ robe are but a few choice items.

MJJA Cave Run and Polar Plunge

Feb. 20, Crystal City, Mo.

Become an underground dweller for a morning of high-speed spelunking as you navigate a 3-mile course that weaves in and out of corridors and caverns. Held inside an old sand mine, runners must deal with mushy sand underfoot, several streams to ford and large dunes to climb. Remember to bring your headlamp!

Twinkie Run

April 1, Ann Arbor, Mich.

What better way to celebrate April Fool’s Day than by running a 5K and indulging in one of America’s unhealthiest foods: the Twinkie. There are two fueling locations where you can partake of the sponge cake. Held annually to raise money for the fight against ALS, this high-caloric race is for a worthy cause.

Caliente Bare Dare 5K

May 1, Land O’Lakes, Fla.

When you are going to be running naked around one of the more upscale clothing-optional resorts in America, you want to look your best. Runners will make one loop within the grounds while similarly non-attired spectators cheer you on. But don’t be fooled: This race is USATF certified and determines the National Championship of Nude Running, so there is a talented field.

Camp Pendleton World Famous Mud Run

June 5–6, San Diego

If you’re looking for one of the tougher mud runs on the planet, look no further than this one. Hosted by the U.S. Marine Corps since the early 1990s, participants endure a 10K with more than 20 obstacles, including several combat-related features that offer a hint of what USMC basic training is all about, such as the 100-foot mud pit at the end that will coat you top to bottom.

Boom Days Pack Burro Race

Aug. 7, Leadville, Colo.

Held every August for the past 68 years to honor Leadville’s mining past, this race requires two participants per team—a human and a donkey. The burro must carry a packsaddle loaded with prospecting gear, while the human needs to have a deep reservoir of patience to navigate his or her burro along a mountainous 22-mile course to the top of 13,300-foot Mosquito Pass and back.

Minnesota Monster Dash Half Marathon, 10 Mile and 5K

Oct. 26, Minneapolis-St. Paul

What better way to wrap up your fall running season than taking to the streets with several thousand other runners all dressed up in their Halloween costumes. The best part of this race is the entire course is downhill and offers you the perfect chance to set a PR.

The Gorilla Run

Nov. 13, Denver

For the past 12 years, hundreds of people have dressed up in gorilla suits or banana costumes and taken to the streets for this 5K to raise money for the Mountain Gorilla Conservation Fund. For $100, racers get their own suit, which they can keep, and entry into the Silverback After Run party. The race itself is held on a flat, out-and-back course.

Runyon 5K

Nov. 15, New York City

This 5K is held entirely inside the hallowed halls of Yankee Stadium. Runners start at the ground floor of the stadium and wind throughout the bowels of the stadium before climbing ramps and stairs to the higher concourses ringing the field. Although you don’t get to step foot on the actual field, you do get to take two laps on the warning track encircling it. 

NYRR Midnight Run

Dec. 31, New York City

Normally the idea of going for a midnight run in Central Park would appeal to very few—how many movies have featured good things happening in the park at night? However, this annual race is different. The gun sounds exactly at midnight when the fireworks light the sky after the golden globe has descended in Times Square, cueing more than 6,000 racers to embark upon a 4-mile trek through the park.

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