The Run Down

This is the first guide in our “Day Tripping” series. For each guide in this series, we take you on a weekend/day trip outside of Chicago.

Up first is Galena, IL, which is about a three hour drive from Chicago, and right on the border between Illinois and Iowa. This small town is basically the opposite of 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. Here’s a run down of some of the places we visited.

1. Stay @Desoto House Hotel
2. Mornign Coffee @Devour Cafe
3. Visit @Dowling House
4. Snacks @The Great American Popcorn Co.
5. Historical Visit @Ulysses S. Grant’s House
6. Burgers and Wings @Durty Gurts
7. Rootbeer Floats @Rootbeer Revelry

Galena Map

The drive to Galena is pretty easy, but the last 45 minutes takes you onto a smaller highway. Try to do the drive during the day time, because there aren’t any lights on that last stretch of highway and there are a lot of curves. Plus, if you go during the day, there are some nice scenic spots to pull over and take in the beautiful scenery.



In terms of where to stay, you’ve got your pick of boutique hotels and B&Bs. We ended up settling on Desoto House mainly because it’s right on Main Street and close to everything. Plus, most of the trip revolves around constant snacking and drinking, so being in close proximity to a bed for an afternoon nap was critical.


After a long drive from Chicago, a caffeine pick-me-up may be in store. Right along Main St., is Devour Cafe – a locally owned coffee shop where you can decompress, snack on a homemade quiche, and sip on coffee. If you are a coffee connoisseur, then you’ll probably appreciate this place even more. They have a whole line-up of specialty coffee concoctions with beans from different regions around the the world.


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


When I think small town America, I think burgers and wings, and Durty Gurt’s does a nice job on both of those. The restaurant itself has this back country yokel theme going on, which makes for a casual/fun/goofy atmosphere. Very friendly staff and fast service — in fact everywhere we went, people were just genuinely pleasant and nice.


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

It’s hard to not notice this place, because once you’re within a 100 ft from 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 whole section devoted to craft sodas.



Prior to becoming President of the United States, and before leading the Union army in the Civil War, Ulysses S. Grant was living it up in Galena as a clerk in his father’s leather goods store.

For you Civil War history buffs, the house he lived in is now a historical monument you can tour. You can stop by Wednesday – Sunday for guided tours of the house and learn a bit about the Grant family and their role in shaping the U.S.


Now back to what we do best — drinking and eating. Our last featured place is Rootbeer Revelry, which is also on Main St. You can guess from the name what this place is all about — rootbeer, but more specifically, rootbear floats.

I’m not a huge fan of rootbeer, but for some reason when you add a scoop or three of vanilla ice cream into a cold mug of rootbeer, all seems right in the world.