You’re heading to Dubuque, the oldest city in Iowa. It’s a Mississippi River town with views of Wisconsin and Illinois; Chicago is only 150 miles away. Dubuque has a historic port, a revitalized downtown, and plenty to keep you busy over a long weekend.
Only a few blocks from the harbor, on the corner of Second and Main Streets, you’ll find the historic Hotel Julien. The hotel hosted Abraham Lincoln, Mark Twain, and, most famously, Al Capone, who used to hide out here. The Beaux-Arts building—which takes up almost the entire block—has since been restored, but you’ll still find a grand lobby, arched windows, and dark-wood furniture. The rooms may have been enlarged and a spa may have been added, but Caroline’s remains one of the best restaurants in the city.

From the hotel, it’s a short walk to the National Mississippi River Museum & Aquarium. The museum is part of the Smithsonian, and it features the William M. Black steamboat, wildlife found along the river, and touch pools to get up close to the some of the critters. From the museum, stroll along the Mississippi Riverwalk. You’ll pass one of the country’s last remaining shot towers, which produced lead musket shots for the military, and the old Dubuque Star Brewery, which is now home to Stone Cliff Winery’s tasting room. Tour the historic building, taste their Riesling and Cabernet Sauvignon, and plan to return to the piano bar later in the evening. And if you continue along the 44-mile trail, you’ll eventually reach Dyersville’s Field of Dreams, where the movie of the same name was filmed.
After exploring the waterfront, ride the steep Fourth Street Elevator—it’s really a funicular—to the top of the bluffs for views of the mighty Mississippi. In Cable Car Square, you’ll find Victorian homes that now house candy shops, jewelry stores, and art galleries. Be sure to stop at the All Things Sweet Shoppe for a maple bacon or a green tea cupcake.
Tomorrow you might cross the river to the Chestnut Mountain Resort—you’ll have river views as you ski down the slopes. Or you might visit more wineries along the Great River Road Wine Trail. But first, it’s time to grab a booth at the Riverboat Lounge back at the hotel. You may not be sitting in Al Capone’s booth, but hopefully they’re still making the same whiskey cocktails.