Galena, Illinois: The Perfect Weekend Getaway from Chicago

Sample Itinerary (from Chicago)
- Day 1: Elgin’s Walton Island, Stockton murals, Galena
- Day 2: Explore Galena including the Galena River Trail, Ulysses S. Grant home, and Historic Galena; Chestnut Mountain Resort, and Casper Bluff
- Day 3: Thunder Bay Falls, Apple River Canyon State Park
Optional: drive over the Mississippi River to Dubuque, Iowa or over the border into Wisconsin

Where to Stay
- The Steamboat House B&B (roughly $220/night)

Where to Eat
- Green Street Tavern in the historic DeSoto House Hotel
- Treats from Elle & Becks and/or Chocolat‘ 229

My Travel Diary
Craving a quick trip outside of the city limits, I started researching the best weekend getaways within a three-hour drive of Chicago. Consistently seeing the same results, it was a no-brainer: it had to be Galena, Illinois. The town is named after a rare mineral that was mined there for hundreds of years by local Indigenous tribes before European-American colonizers settled in the area in the early 1800s. The population quickly exploded and by the 1860s it even served as the headquarters for Ulysses S. Grant’s presidential campaign – the DeSoto House has painstakingly preserved many mementos that are worth seeing. The Ulysses S. Grant Home State Historic Site is also a must-see if you're interested in learning more about the man and his family. Nowadays, Galena is decidedly less populated, but far more tourist-friendly. From our comfortable B&B to the incredible architecture and delicious food, it's an easy and enjoyable time.

We spent our time there shopping, admiring the architecture, eating, and wandering the river walk. People were generally friendly and we chatted with many locals (masked, and at a distance). At the time, the pandemic was still raging and vaccinations weren’t yet ubiquitous. Unfortunately, these are political times: from the pandemic to the recent election, and some people were hiding their faces but wearing their opinions on their sleeves. I entered one business and casually made small-talk while the woman working there rang up my purchases, asking how they’d been faring in light of the travel restrictions, mask restrictions, etc. She told me that they hadn’t had many issues with people refusing to wear masks or protesting in Galena. “That’s fantastic. Everything’s so political these days, but I think most people just want everyone to be healthy and happy” I naively responded. She then launched into an angry diatribe about why Biden was destroying the U.S. and her thoughts on the insurrection (among other things). So, I firmly told her that this conversation was over and I was leaving her store. When you travel, there’s always the good and the bad, but sometimes there’s also the ugly: in this case it was political polarization popping up seemingly out of nowhere.

Aside from that unpleasant encounter, everyone was respectful – not trying to proselytize or pressure in any way. Yes, I set a low bar. I particularly enjoyed chatting with the owner of Elle & Becks, and the woman working in Chocolat’ 229: friendly, laid-back, flowing conversations, exactly what I’d expect on a small-town getaway. What I didn’t expect was a nice evening stroll being blaringly interrupted by a siren straight out of the movie “The Purge”. My instinct? Powerwalk toward the nearest open restaurant as quickly as possible. My partner’s response? Abruptly stop and check his phone. Guess who’s still alive? Both of us, thankfully! It turns out that some small towns have volunteer fire departments, which summon their firefighters through the use of a painfully loud siren. And apparently said siren must be tested daily to ensure it’s still functional. It was. In comparison, our B&B was located just off the main drag, so it felt like a really calm retreat. We were the only guests staying there at the time, which magnified the sense of healthy isolation that I had craved. The breakfasts were delicious, the décor was still Christmas-oriented, and we spent a good amount of time just relaxing in the various rooms throughout the historic home. I even had the opportunity to play piano to my adoring fans. Well, my one and only fan – but he really enjoyed it!

We also made sure to take in the nearby sites like Chestnut Mountain Resort, which would be a good place to learn how to ski or snowboard. Sadly, I wasn’t interested in either, but I did appreciate the view!

We continued on to the local Thunder Bay Falls, which were very different from the Canadian version. This was an odd stop because you have to park by the road and then walk over to see them, yet it’s hard to get a nice view of them without the surrounding developments that have sprung up.

Casper Bluff, in contrast, was much more rural and a really peaceful place to walk and appreciate the wide-open skies. It’s also a perfect spot for birdwatchers, even the kind who might usually only watch the blue jays and cardinals on TV.

Farther from Galena is Apple River Canyon State Park, which is worth a visit. We didn’t hike so much as casually walk through the park for about an hour before deciding to move on to our next destination. The highlight for us was playing in the snow: it felt like our own little winter wonderland.

Finally, I’ll just mention some of our stops on the way to and from Galena. We really liked Walton Island Park in Elgin, just outside of Chicago. It was very slippery, but it also had a Narnia-esque vibe to it.

Stockton was a sweet little town full of pretty murals, well worth a stop.

And although we didn’t spend much time in Dubuque, we were glad to have crossed the bridge into Iowa just to see the power of the Mississippi and remember how far it travels across the U.S. Maybe in the future, our travels will take us further afield but for now we’re happy just enjoying the local terrain.