A thousand Santas ditch the sleigh in favor of bikes in downtown Milwaukee

On a chilly Saturday morning, more than a thousand people donned Santa suits and cruised through the streets of Milwaukee for the Santa Cycle Rampage, an annual ride for holiday merry-making and cycling advocacy.

First-time rampager Mark Hense was part of a sea of festive red, and kicked things off with a shotski — a line of shot glasses glued to a ski, allowing for several people to down a shot in unison.

"I think once you get soaked up into an ocean of Santas, it's something that is to behold," said Hense, who lives in Wauwatosa, a Milwaukee suburb.

The Santa Cycle Rampage started 20 years ago as a pub crawl among friends. People saw how much fun the group had and things snowballed from there. The event has grown so much, it now boasts this bulky superlative: "the world's largest, holiday-themed costume bike ride for charity."

"It's a little tagline I came up with a couple years ago," said Jake Newborn, assistant director of the Wisconsin Bike Fed, the cycling nonprofit that's since taken over coordinating the rampage.

The event has inspired similar rides in Boston, Kansas City, Minneapolis, and Fort Collins.

This year, the Bike Fed expected 1,800 Santas, elves, reindeer, and Grinches to participate. Most cyclists register in advance. The registration fees, along with donations collected, help the nonprofit advocate for accessible, safe biking across the state and set up biking education programs for children and adults alike. Last year, between this ride and a sister ride in Madison, the group raised $50,000.

The rampage also celebrates winter biking in a part of the country where cold and snow doesn't end outdoor play.

"I started the Rampage after seeing Chicago had a similarly-titled event," wrote former Bike Fed executive director Dave Schlabowske, of the history of the ride.

"I thought a Milwaukee version would encourage more people to see how easy it is to ride in the colder months and to reward the few who already did with a fun event."

With turnout growing each year, some declare the ride is the "gateway drug" to winter biking.

"Biking doesn't just stop in September, people bike all year round," Newborn said. "This is really something that has grown to be a tradition where people now are doing it every year. They've got costumes, they've got special bikes for it."

Many riders decked their bikes with tinsel, lights, and candy canes. One cyclist, Mark Rowe, went above and beyond, building a plywood sleigh enveloping his bike. Construction began last year, when he and a friend built sleighs to decorate their front yard for the holiday season. When it was time for the Santa ride, he decided to put the sleigh on a trailer and tow it with his bike.

"That was a little problematic," he said. "We had some design issues. So this year, I thought, if I can ride my sleigh, that would be even better."

Rowe declined to say quite how long that project took.

"We'd like to probably not quantify that because significant others may not appreciate how much time we've been spending on it," he said. "But a lot of time."

Six miles north from the starting line, around the ride's halfway point, Scott McBride and a friend were on the road when a crowd of Santas invaded. The pair were heading to a COVID-19 booster appointment, and later, a Marquette University basketball game.

"We're stuck here for a while, but that's okay," said McBride, from the driver's seat of his convertible. "Santa's promised he'd give us extra gifts for waiting for his parade."

Cyclists said it was a thrill to take back the streets.

"We love it," said Sherry Steward, who was dressed as a Christmas tree. "It's anarchy."

"It's how the world should be," said her husband, Tyler Steward, who e-bikes to work and came to the rampage in an ugly Christmas cat sweater.

They said the event is the only day that when Milwaukee drivers honk, it's not out of anger, but holiday cheer.

It's "in a good way!" Sherry said. "We stop traffic."

To be clear, the rampage is not a race. It's a slow roll. Along the way, groups split off to visit bars and restaurants that welcome cyclists to break for milk and cookies — or beer and cheese curds, a Wisconsin delicacy.

Outside the popular Lakefront Brewery, Tonieh Welland said she needed some holiday cheer. Her mother had surgery yesterday.

"I love biking outside in the cold, even though I am not fit for it as a Liberian woman," Welland said, before offering a rendition of "It's the Most Wonderful Time of the Year."

An advocate for cyclist and pedestrian safety, Welland said the rampage is more than just drinks and costumes — it's visibility for the cycling community.

"Cars see all these people riding and they're like, 'Oh, I'm a little bit more aware of people on the road,'" she said.

Welland and her friends mounted their bikes, ready to head to their next stop. She pulled out her phone and blasted Mariah Carey's "All I Want for Christmas Is You."

WUWM's Maayan Silver contributed to this story.

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