It took the better part of two days to ride nearly 1,300 kilometres from Winnipeg to Milwaukee for Harley-Davidson’s 115th anniversary party earlier this month — yet, miraculously, the moment we arrived, I felt like a kid again.
My flashback to childhood occurred when we roared into the parking lot of our hotel for the weekend and I spotted my big brother, Allen, polishing his gleaming Harley-Davidson under a blazing Wisconsin sun. Allen, who is 18 months older than me, had ridden a long way too — his journey began two days and 1,200 km prior in Ottawa.
A big hug from Big Al reminded me we were in town for a fun-filled bro weekend loaded with laughs and adventure. Milwaukee, Harley-Davidson and Big Al totally delivered on all fronts.
This was my third trip on a motorcycle to Milwaukee for a Harley-Davidson anniversary party; I previously made the trip to the rally in 2008 and 2013. Every five years, the Motorcycle Company, the City of Milwaukee and the surrounding area host a bash to celebrate not only the iconic brand founded in the city in 1903, but also the lifestyle and camaraderie that seems to go hand in hand with owning and riding a Harley-Davidson.
On past trips I had a terrific time travelling with Dave Gray, the owner of Harley-Davidson Winnipeg, and his crew, but this time around I had two fewer days to make the long ride to Milwaukee and back. I opted instead to travel in a smaller pack with my friends Don Swirsky and Dave Wolfe.
The three of us rolled out early on Thursday morning with Swirsky, who is a skilled rider and gifted navigator, in the lead. After crossing the border, we blasted through Minnesota with only short stops for fuel and to stretch our legs in Warroad, International Falls and Duluth, before arriving at our stop for the night in Eau Claire, Wisconsin. It’s about 900 km from Winnipeg and home to some of the friendliest folks in America — every person we met was genuinely interested in our trip and full of compliments for our shiny motorcycles. There’d be plenty more of that kindness and hospitality in store for us throughout the weekend.
Because we had ridden so far on Thursday, our scenic ride from Eau Claire into Milwaukee on Friday took less than four hours and we arrived under a hot sun just after lunch.
One of the great things about the Milwaukee Harley rally is that it doesn’t take place in only one spot. There is so much to see and do throughout the weekend, in Milwaukee and all around the surrounding area. The local Harley dealers, of which there are many, all get involved and host huge parking lot parties with live bands, great food and all sorts of motorcycle-related vendors who sell parts, clothing and accessories. It’s basically a carnival of chrome everywhere you go.
On Friday afternoon we checked out a couple of those dealership parties, made some new friends, then rode downtown for dinner. Allen led us to a Mexican restaurant named Conejito’s Place, a small but popular spot we discovered purely by accident when we were in Milwaukee together back in 2013. Don helped Allen and I demolish a table covered in delicious tacos and enchiladas served on paper plates. Dave, who is about the fittest biker I’ve ever travelled with, seemed to enjoy the chips and salsa.
Following dinner we made our way to Brady Street, which was closed to all vehicles except motorcycles. A sea of bikers, all clearly having a really good time, welcomed us with open arms, and although it was ridiculously hot and crazily crowded, it was also about the best fun I’ve had all summer — and it was a really fun summer!
Saturday morning we woke to rain, so I rolled over and stayed in bed. Allen, Don and Dave toured a couple more dealerships in the morning and got soaked. I was a tad upset we missed the motorcycle races that afternoon at Bradford Beach, but the folks I talked to who did make that scene said although the races were fun to watch, by the time they got out of there, their bikes and boots were covered in muck. Oh well, there’s always next time. Plus, I needed the rest.
The forecast looked grim for Saturday, but thankfully in Milwaukee they are about as good at predicting the weather as we are here, so the sun arrived at about 3 p.m.
Big Al planned a trip within our trip to a spot he’d heard about called the Knucklehead Pub & Grub in nearby Eagle; it’s about an hour’s ride from Milwaukee through scenic Wisconsin farmland, rolling hills, sweeping turns and some very smooth asphalt. It was a really fun spot, the food was great and the ride was greater.
I spend a fair amount of my time at rallies wandering around trying on biker rings and posing for selfies, while my brother talks to locals and finds the best rides to take and all the spots where the action is. He always knows exactly where he’s going and is an excellent and safe rider. There is no one on Earth I’d rather follow around than Big Al.
We rolled out of Eagle with the sun setting on our backs and a lightning storm brewing in our mirrors, but the weather gods were on our side and we made it back to a hot and muggy — but dry — Milwaukee just in time for another raging party on Brady Street.
The collection of amazing motorcycles found lining those streets was a thrill for the senses. It was impossible to see it all, but I spotted practically every model of Harley-Davidson ever made, as well as custom creations that easily cost more than $100,000 to build. The big bagger with a big front wheel and an even bigger stereo seems to be where the custom builders are dropping their coin, and although I honestly just don’t get it, you have to hand it to these guys: the amount of time, effort and money they have invested in these machines is staggering and commendable.
We finished the night with a small party of our own in Dave and Don’s hotel room, where we swapped stories about all the funny, crazy and downright beautiful things we’d witnessed in Wisconsin. Trips like this really help friends bond, and we all agreed it was a spectacular weekend.
Back in July, I had the good fortune to travel to Prague in the Czech Republic for the European Harley-Davidson party, and although it was a dream trip loaded with fun and excitement, I will say this — if you want to get treated like rolling royalty, ride a Harley-Davidson through Wisconsin. These folks not only give motorcyclists tremendous respect on the road, they also go above and beyond to make bikers feel at home in the state where it all began.
Don and Dave rolled out early on Sunday morning, while Allen and I got going a bit later. We waded through a steady drizzle from Milwaukee to Stevens Point, Wis., where the hot tub at the Holiday Inn was calling our names.
My big brother and I bid a fond farewell to one another on a cloudy Monday morning in the middle of America. The words “I love you man” were surely shared!
I rode alone all day and into the night for more than 1,100 km, and made it home literally moments before that big storm crashed Winnipeg.
In five short days I’d ridden 3,000 kilometres — and although it felt great to be home, when I laid down for some much needed sleep, plans of all the fun we’re going to have in Milwaukee when we return in 2023 ran through my head.