I Tried It: The UPAF Ride for the Arts

Traverse the Hoan Bridge by bike at this annual Milwaukee cycling tradition.

There’s nothing quite like kicking off summer by riding headlong into lake-fueled breezes, pumping your legs with all your might and getting up close and personal with nearly 4,000 spandex-clad strangers. Such is the sweaty, joyous experience of the annual United Performing Arts Fund (UPAF) Ride.

My husband and I signed up for the ride for the first time in 2014 at the encouragement of a cycle class instructor, and we’ve ridden every year since, except for one. It’s become one of our favorite harbingers of the warm, get-outside-all-you-can, patio-weather season.

Welcome to Summer. Hop on your bike.

The UPAF Ride, which is the largest annual fundraiser event for the organization dedicated to furthering the arts in the Milwaukee community, is always the first weekend of June. This year’s ride will take place Sunday, June 2.

Because of that tricky changing-seasons timing, the weather is akin to Forrest Gump’s box of chocolates and you never know entirely what kind you’re going to get. Some years, those lake breezes will chill you to your bones, sometimes a rain jacket is a must and, still other times, the stars align and it’s downright sunny and delightful.

The great appeal of the UPAF Ride is that there’s truly a ride length for everyone — whether you’re a dedicated cyclist or a ride-for-fun type, with 5-, 12-, 25-, 45- and 70-mile options. The first year I did the ride, I was crazy-ambitious and signed up for the 45-miler. It was fun and exhausting and amazing, and I’m nowhere near in shape to tackle that one in 2019.

“Own the Hoan”

The past few years, I’ve opted for the 25-mile ride, and it’s proven to be a three-little-bears level of just right – long enough to feel like I get a proper tour of the city (and some exercise) without feeling utterly spent at the end. Plus, you get to ride over the Hoan Bridge, which provides stellar views of the landmark bridge and of the city. And, as an added bonus, you’re not too sweaty or jelly-legged to get brunch with friends afterward. (The ultimate “you did it!” reward.)

The drill is essentially like this:

– Get to the Summerfest grounds around 7 a.m. (Timing varies, based on what ride you’re doing.)
– Nab a parking spot conducive to an easy exit. As we all know, parking in the Third Ward can be tricky, so get there early!
– Do a final inventory: tires have air, check; helmet, check; water bottle, check.
– Line up with fellow riders.
– And, finally, ride like the wind!

In The Saddle

My bike is an old Trek road bike I bought secondhand from a shop in Cudahy (Shout out to South Shore Cyclery!). I don’t ride her near as much as I’d like, but she’s been my trusty set of two wheels for each UPAF Ride.

At the start of the ride, the gaggle of bikes with front tires akimbo, nosing into one another in knock-kneed fashion is a sight to behold. It’s a tangle of road bikes and mountain bikes and hybrids and fat tires. Astride them are elite riders and casual riders and old people and young people and kiddos. It’s a fantastic amalgamation of people who have in common a simple joy of cycling.

As the faster riders break from the pack, the cluster of riders loosens and the true beauty of the ride begins: past the Summerfest stages and then up and over the Hoan. The views are so perfectly Milwaukee and so perfectly… perfect. To the west of the bridge: smokestacks and squat brick industrial complexes. And to the north, the shiny, skyscraper-dotted skyline. Lake Michigan is to the east.

At the end of the Hoan, the ride weaves through the bungalow-dotted streets of Bay View. Families gather on porches to cheer on the riders and wave in encouragement. Southward, riders roll on to Grant Park.

The “oasis” water-and-snack stop at Grant Park is a sight for sore legs. Typically, a group of live musicians is set up playing in one of the picnic pavilions. It’s a nice reminder of what the ride is truly all about: the symphony performances and plays and cultural events that have come to define Milwaukee.

After refueling at the oasis, it’s back in the saddle, back Downtown, lake-fueled breezes and Cream City views aplenty once more.

Back at the Summerfest grounds, a celebration is in full force. Park your bikes in the designated bike lot, and head in for some adult refreshments on the house. Cheers to a successful ride through our beautiful city!

Sign up for the 2019 UPAF Ride today. Registration is $65-75, free for riders 12 and under.