French Catholic Jesuit missionaries were the first Europeans to pass through the region of southeastern Wisconsin, ministering to fur traders and Native Americans. In 1818, the French Canadian explorer Solomon Juneau settled in the area, and nearly 30 years later the town was incorporated as the city of Milwaukee. Large numbers of German immigrants arrived during the late 1840s, which started a brewing movement that eventually made Milwaukee famous. My ancestors came from Belgium in the 1850s, settling in Kewaunee County northeast of Green Bay.

Harley-Davidson Sport Glide
The author’s son Henri will be riding the new Harley Sport Glide.Harley-Davidson
In 2017, Milwaukee, Wisconsin, was the 31st largest city in the US, with an estimated population of 595,

In 1903, William A. Davidson, Walter Davidson, Sr., Arthur Davidson, and William S. Harley laid the groundwork for a company that continues to put Milwaukee on the map. The eponymous company celebrates its 115th anniversary this year, with plans for a huge shindig over Labor Day weekend. A timely family reunion in Wisconsin this weekend prompted my son Henri and I to take advantage of summer weather to ride Harley-Davidsons from Milwaukee westward back to our home in the Bay Area in northern California.

Henri was born in Milwaukee in late November of 1994. The city has changed visually in the last 23 years, adding a $100 million wing to the Art Museum designed by Santiago Calatrava, a new Brewers' stadium called Miller Park, and in 2008, the 130,000-square-foot Harley-Davidson Museum along the Menomonee River, housing more than 450 bikes and drawing nearly a half-million visitors a year.

Harley-Davidson Museum
The Harley-Davidson Museum is celebrating its 10th anniversary.Gaz Boulanger

Milwaukee was our home for five years in the early '90s. Summerfest continues to draw top musical acts during early July, and River West and the Third Ward have been renovated to a high luster since we moved away. Milwaukee is experiencing its heaviest makeover since the '60s, and it sparkles in the summer. Our favorite things about Milwaukee are Colectivo Coffee, Sprecher root beer, Café Hollander, Fuel Café, and Kopp's Frozen Custard. Henri's mom went into labor the morning following a hardy meal at Kopp's, and she's usually the first one to recommend a visit when we're in town.

We picked up the Harleys at The Motor Company’s world headquarters on Juneau Avenue today, a couple blocks north of Miller Brewery, and just two miles from Miller Park.

Henri’s Bike: 2018 Harley-Davidson Sport Glide

Harley-Davidson Sport Glide
The new Harley-Davidson Sport Glide weighs 670 pounds dry, and starts at $18,599. The inverted front fork and a new rear monoshock with external preload adjustment allow the rider to customize his handling profile.Harley-Davidson

Gaz’s Bike: 2018 Harley-Davidson Heritage Classic

Harley-Davidson Heritage Classic
The nostalgic Harley-Davidson Heritage Classic weighs 697 pounds dry, and starts at $18,999.Harley-Davidson

After careful consideration, we chose our Softails based on several criteria, including a larger 5-gallon tank, Harley’s Milwaukee-Eight 107 engine, locking saddlebags, and 1,746cc of touring power. Weight is comparable; dry, the Sport Glide dry is 670 pounds, while the Heritage Classic is 697 pounds, giving Henri a 27-pound edge with The Motor Company’s newest model.

Our tour will include some major interstate riding, so a proper windshield was key. Henri liked the ergonomics and position of the Sport Glide, as well as the simple lines. He’s an artist, and digs minimalism.

I, on the other hand, am a bit nostalgic; more chrome, a cop windshield, and higher bars, plus footboards for the long haul. We didn’t care for oversized top cases or Infotainment. We’re packing light, so everything we need will fit into the locking saddlebags, with no need for backpacks. We just want to cruise along and enjoy the scenery. It’s not every day we get to ride through Big Sky country!

The Softail choice was made for comfort and handling. We’ll be climbing several peaks once we cruise through Wyoming, Montana, and Idaho, so lighter, more nimble bikes were important.

Up next: Experiencing northern Wisconsin by bike, touring my childhood neighborhood, and exploring where my father grew up northeast of Green Bay.