The Trip: A weekend in Milwaukee
This fall, point your motorcycle toward Milwaukee, where the Harley-Davidson Motor Co. is celebrating its 105th anniversary and the unveiling of the Harley-Davidson Museum (it officially opened in July). Wisconsin is Harley country — but whether you travel via the classic roadster or another brand altogether, Milwaukeeans are famously fond of motorcycles. You’ll find your leathers, boots and bike are welcome nearly everywhere.
Instead of braving Chicago traffic, travel to Milwaukee by way of Michigan. Most of the state’s expressways parallel secondary routes, with fewer trucks and better views. This route also reduces drive time by two hours. Head for Muskegon and rest your legs while the Lake Express ferries you and your motorcycle across Lake Michigan and into the heart of Milwaukee.
Once there, check into the Iron Horse Hotel, the nation’s first luxury boutique hotel catering to motorcyclists. Indoor parking, a high-powered bike wash and in-room storage facilities for leathers, helmets and boots make bikers feel at home. You’ll also have access to personalized ride maps and gourmet saddlebag lunches.
Refuel at the Milwaukee Ale House in the historic Third Ward. A 19th-century brick-and-timber microbrewery, the Ale House serves everything from veggie wraps to bratwurst made just across town at Usinger’s.
Only a canal separates the Iron Horse from the Harley-Davidson Museum. You can walk, but you might prefer to display your bike alongside dozens of others parked in front of the steel-and-glass museum. Inside, Harley-Davidson displays hundreds of crown jewels, from the 1903 Serial No. 1 (Harley’s first motorcycle) to Elvis’ 1956 orange-and-white KH.
To see where Harley-Davidson gets its rumble, ride west to the Milwaukee suburb of Wauwatosa to Harley’s Powertrain Operations, where one-hour plant tours showcase Sportster and Buell engines and transmissions in production.
Back in town, eat at least once at Sobelman’s Pub and Grill, in a century-old tavern once owned by Schlitz. This is the home of Milwaukee’s best burger, a Black Angus patty served on a soft butter bun. Wash it down with a Bloody Mary (it comes with a garnish so impressive the drink almost qualifies as a salad) or Milwaukee’s local Sprecher Amber.
Before you wrap up your getaway, grab a bite at Trocadero, a French-inspired bistro that scores high marks for its weekend brunch (crepes and omelets made with locally grown ingredients). Lastly, ride over to the House of Harley-Davidson, one of the world’s largest Harley dealerships. If it can sport an “H-D,” you can buy it here. Ask the service department to tune up your bike before you hit the road, or just follow tradition and buy a T-shirt emblazoned with the local dealer’s name and city. After all, a weekend in Milwaukee is one you’ll want to remember.