Most festivals have music. 

Some have parades. Others might have food trucks.

But in Cripple Creek, the historic town’s biggest event has one attraction that always steals the spotlight: racing donkeys. 

For one weekend each summer, Cripple Creek’s Two Mile High Club transforms Bennett Avenue into a racetrack for the annual Donkey Derby Days.

Returning for its 95th year, the festival will bring thousands of visitors Friday through Sunday for donkey races, family activities and a tribute to the animals that helped build Cripple Creek’s legacy.

“It’s a weekend of family fun,” Two Mile High Club President Annie Valades said. “It’s filled with music, vendors and food trucks, and best of all, donkeys. It’s probably one of the only places in the United States where you’ll find donkeys running up the main street of a town racing.” 

So before hoofbeats hit downtown Cripple Creek, here’s what to know before you go. 

The story behind Cripple Creek’s four-legged mascots 

Long before tourists filled the casinos and race spectators lined Bennett Avenue, donkeys were some of the hardest-working residents in Cripple Creek.

In the early 1900s, the animals hauled ore and helped power what was once known as the “world’s greatest gold camp,” according to Mayor Annie Durham. Their short stature made them well suited for the mines, while their strength allowed them to carry heavy loads. 

But when mining operations became more mechanized in the 1930s, many of the donkeys were no longer needed. Rather than relocating them, mine owners simply turned them loose across town.

“A group of business owners saw these donkeys hanging out all over town and said, ‘Folks, we need to step up and take care of them the way they took care of us in the mines,’” Valades said. “People pitched in, feeding them at night and making sure they had food and water. Since then, donkeys have always been synonymous with Cripple Creek.”

The effort to care for the donkey herd eventually became known as the nonprofit organization, the Two Mile High Club.

“We have a much older group of donkeys now because we take such good care of them,” Valades said. “But many of them require medicine or special senior food. We have to house them, feed them, get water for them, clean up their corrals and buy halters. It takes probably three to five thousand dollars per donkey, and we have 16 donkeys to care for.”

Funded through donations, grants and proceeds from events like Donkey Derby Days, the organization relies heavily on community support to keep the herd healthy.

Fortunately for spectators, their most successful fundraising idea just happens to be a mix of competition, comedy and chaos. 

The main event: Donkey racing

After registering online with a $100 entry fee, participants can choose from several divisions of racing groups, including media, first responders, fun races and more. Saturday and Sunday feature the community races throughout the day, with Redonkulous Ranch Sanctuary & Rescue’s professional pack burro racing available only on Sunday. 

Each team consists of two people and one donkey. While one person leads the burro with a carrot, the other helps guide it up Bennett Avenue, only completing the race once all three cross the finish line. 

Of course, a race involving donkeys comes with one guarantee: absolutely nothing is guaranteed.

“The donkeys might be running along just fine, but then they get a whiff of somebody’s kettle corn,” Valades said. “That’s how they’ll stop and people will pass them by, so there’s just no telling who’s going to win.”

Winners earn prizes like trophies and a one-night stay at The Broadmoor to $100 gift cards for places like Walmart, Saltgrass Steak House, AJ’s Pizzeria and Judge’s Char-Grill.

Even finishing last comes with its own reward: the Dead Ass Last award, featuring a donkey’s backside in the form of a trophy.

Then there’s the festival’s messiest contest: the Donkey Poop Drop.

On Sunday, 500 numbered squares are painted or taped onto the road and sold to hopeful participants. The square that ends up with the most donkey droppings wins a $500 cash prize.

As for cleanup? Local kids join with scoops in hand, competing for cash prizes awarded to the top poop collectors.

“The games have changed since back then,” Valades said. “They used to have spitting contests, longest beard contests and greased pig contests. Now we have poop drops and more modern things like music and entertainment.” 

More than just donkey business 

The donkeys may be the stars of the show, but the festival itself offers so much more.

Friday includes a beer garden, vendor market and concerts spread across three stages. Saturday starts with a pancake breakfast followed by the annual parade at 11 a.m., before races and live music take over the rest of the day. Sunday’s schedule mirrors Saturday’s festivities, with professional pack burro races included.

Families will also find plenty to entertain younger visitors in the children’s zone, all while witnessing a vintage aircraft flyover. 

“For a little town like ours to have an airplane flyover, an army marching band, horses, concerts, cool cars, a bagpiper and just all kinds of things, it’s just wonderful,” Valades said.

Performers include Wild Blue Country from the U.S. Air Force Academy, Just Us, Mimic, The Martini Shot, rising country artist Maddox Ross and more.

Those looking to take home more than memories can also participate in the festival’s online silent auction. As an addition to the event in recent years, the auction has grown from about two dozen donated items to nearly 100, with bidding open from 10 a.m. to 4 p.m. Saturday.

Then, there’s the endless food options.

“We have all kinds of food,” Valades said. “Anything you could want from fresh doughnuts to Philly cheesesteak sandwiches, kettle corn, all kinds of barbecue, corn on the cob, hamburgers, hot dogs, Italian food and Thai noodles. That, plus all the fun, it’s like going to a state fair.”