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Sun or snow, this Milwaukee cycling group keeps rolling

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Scrappy Hour; Instagram

They lift your spirits, prompt you to think, make you feel grateful and inspire you to do more. They connect you to our community, shining a spotlight on what's good about our city. They're stories that are Uniquely Milwaukee, sponsored by the Milwaukee Public Library.

In the middle of Milwaukee winter, most of us are used to being outside and active if the conditions are juuust right. But there's a cycling group that meets every month — warm or cold, rain or shine — to ride and connect.

Kenny Siebert is one of the founders of Scrappy Hour, and when I joined for a late December ride on a foggy and overcast morning, I asked him how it all got started.

“A couple years ago, my friend Brian was moving back from New York, and out there there were a bunch of social run clubs,” Siebert recalled. “We wanted to start a social running and cycling club … something more for the community, something that got people out on bikes.

“At the time, we had both learned a lot about the worldwide phenomena of coffee outside, where people go to weird places, make coffee, have coffee, enjoy each other's company. We wanted to bring that to our community in Milwaukee. So we just started making Instagram posts about it, and the first time I think 12 people showed up.

“We've had rides with upwards of 75 people in the summertime when it's really nice. Unfortunately, today it's pretty crummy outside. So we'll see who actually shows up, who wants to actually come out for the last ride of the year.”

Two of the people who showed up were Alex Allgood and Abbey Osborne, who discovered the group online but quickly took their interest in it offline.

“I heard about it through Kenny and Instagram more than likely,” Allgood said. “Brian used to live above me before he moved to New York, and being a cyclist enthusiast and just wanting to build more of my friendship circle, it seemed like a great way to do that at least once a month and meet new people and kind of put myself out there.”

“I also found it on Instagram,” Osborne noted. “I bike by myself a lot of the time, but I thought it was great to have a place to sort of cycle together in a community and to see more of the city, hang out with new people, see old friends.”

The group typically meets on the last Sunday of the month, rolling out from places like Cactus Club and The Daily Bird, with riders of all kinds joining in.

“Usually it's the last Sunday of the month. Every once in a while, we'll get our calendars messed up because it is just two guys doing it for free on Instagram,” Siebert joked. “But, for the most part, it's going to be the last Sunday of every month. … We try to keep [the rides] to a total of 16 miles or less round trip, and we do a very, very casual pace. We've had riders as young as 7 and as old as 80 doing this ride. So it's for everybody.”

And if you don't feel quite empowered enough to ride in the winter, Siebert is right there with you.

“If riding in the winter isn't your cup of tea, that's totally fine,” he said. “There should be no shame in that. I mean, there's a lot of mornings where I get up, and I want to be in sweatpants on my couch, cuddling with a dog. But I come out here and make sure everyone's doing a good job and being safe and having fun. I think once you get wet or you get cold, you're hopefully not going to get much wetter or colder. So you kind of just have to embrace it.

“And then you have to think of the upsides, where you’re getting fresh air, you're getting a little bit of exercise, and you're going to feel good that you did it. It is a minor accomplishment going through the hardness of winter riding. It's something to be proud of at the end of the day.”

To learn more about Scrappy Hour, including info about future rides, follow them on Instagram.

Director of Development | Radio Milwaukee