The Run Down

This guide has you hitting the road for a weekend trip out of the city. You'll visit Galena, IL, about a three-hour drive from Chicago and on the border between Illinois and Iowa. This is the opposite of the hustle and bustle of Chicago — it’s a small town situated amongst rolling hills, and its big draw is a picturesque main street full of small boutiques and restaurants.

1. Stay @ Desoto House Hotel

2. Visit @ Dowling House

3. Burgers @ Durty Gurt's

4. Snack @ Great American Popcorn Co.

5. Visit @ Ulysses S. Grant's Home

6. Drinks @ Root Beer Revelry

1. Desoto House Hotel

In terms of where to stay, you’ve got your pick of boutique hotels and B&Bs. Desoto House is perhaps the most convenient because it’s right on Main Street and close to everything. Plus, most of the trip revolves around constant snacking and drinking, so being near a bed for an afternoon nap is critical to this guide.

As the oldest operating hotel in Illinois, opening its doors in 1855, it leans into its mid-19th-century  design, with 55 Victorian-style guest rooms. The history of this hotel is just as much of a reason to stay as any.

Built during the town’s economic peak when Galena was a central river port, the hotel was the city’s crown jewel. Galena flexed its political importance, attracting notable figures like Abraham Lincoln, who gave a speech on the hotel’s balcony, and Ulysses S. Grant (more on him later in this guide), who used the hotel as his presidential campaign headquarters.

2. Dowling House

Continue the walk down Main Street, and you’ll run into the oldest house in Galena, built in 1826. They have scheduled tours to take you through the house and give you a history of the town and the home itself.

The tour is a brisk 30 minutes. You’ll find the home preserved with primitive furniture and artifacts common to the time. It makes you wonder how people lived like that, but I’m sure a hundred years from now, people will be wondering the same way about us.


3. Durty Gurt’s

When I think of small-town America, I think of burgers and wings, and Durty Gurt’s does an excellent job on both. The restaurant itself has this backcountry yokel theme going for it. It’s casual, goofy, and has established itself as a fixture in town.

They make all sorts of burger concoctions. They got your basic half-pound cheeseburger but also hefty varieties like ones topped with eggs, a pile of onion rings, and bacon. 

4. Great American Popcorn Co.

After indulging in burgers and wings, drop by the Great American Popcorn Co. to continue your food binge.

It’s hard not to notice this place because once you’re within 100 ft of the door, you’ll be overwhelmed with the scent of freshly popped popcorn.

As a kid, this store is what I imagined heaven would be like. It’s filled with shelves of assorted popcorn, homemade fudge, an ice cream parlor, and a section devoted to craft sodas.

5. Ulysses S. Grant’s Home

Before becoming President of the United States and leading the Union army in the Civil War, Ulysses S. Grant was a clerk in his father’s leather goods store in Galena.

Following the war, he was granted a hero’s welcome and was presented with this house. It now serves as a historical monument you can tour. You can stop by Wednesday – Sunday for guided house tours and learn about the Grant family and their role in shaping the U.S.

6. Root Beer Revelry

Now back to what we do best — drinking and eating. Our last featured place is Root Beer Revelry, which is also on Main Street. You can guess from the name what this place is all about — root beer, but more specifically, root bear floats.

You’ll find 50+ different varieties of beer from all over the country and multiple root beers on tap. It’s like a craft beer bar, but for root beer.

Root beer sommeliers can educate you about the different varieties and based on your preference, will serve you up straight from the tap or over ice cream.