Weekend in Galena By Josh Johnson, The Kentucky Gent

Weekend in Galena

Exploring the charming, historic city

By Josh Johnson, “The Kentucky Gent

Read more

The older I get the more I appreciate a weekend trip. When I was younger, if it wasn’t a weeklong trip I wasn’t interested in going. Now I definitely realize that I’d rather take several shorter trips vs. one or two long trips, and my weekend trip to Galena was no exception.

I took a midday flight out of Louisville, and by the time I was settling into my seat we had already begun our descent into Chicago. Once I landed, I was on the road to Galena just in time to beat most of rush hour traffic. I loaded up my latest audiobook and began the 2½ hour drive to Galena. Before I knew it I was driving through cornfields, past antique malls and rolling into the quaint downtown of the city. I felt right at home. Because truth be told, my hometown looks a lot like Galena.

I felt right at home. Because truth be told, my hometown looks a lot like Galena.

Slowly I drove through the downtown area. Taking in the sights, sounds and the people who both call this place home or were visiting like myself. I made mental notes of all the places that I wanted to check out as I approached my home away from home for the weekend—Jail Hill Inn.

Share this story

Where to Stay

Jail Hill Inn is a 135-year-old, 4-story brick building, which served as the county jail for nearly 100 years. It has now been transformed into Galena’s premier bed and breakfast. It’s tucked back off of Main Street but still easily within walking distance of everything that downtown has to offer. Not to mention, due to its location it affords guests sweeping views of the entire city.

It’s been expertly renovated and outfitted by innkeeper Matthew Carroll. He’s also a treasure trove of knowledge on what to do while in town so take full advantage of his expertise when you check in. The inn is full of touches that make the experience something special, including chocolates and chilled champagne waiting in my room, gorgeous furnishings through and room keys that look like padlocks for a fun nod to the building’s history. Not to mention, you can start every day with a three-course, made-from-scratch gourmet breakfast in the first floor dining room. It’s the perfect way to start your day of exploring!

Share this story

What toDo

Depending on how you like to spend your weekends, there’s a little something for everyone. I did my best to dabble in a little bit of everything, and literally only ventured off Main Street once. There’s a reason it was named “Best Main Street in The Midwest” by Midwest Living magazine and one of “America’s Best Main Streets” by Fodor’s. Everything you could want to check out in Galena and then some is nestled perfectly on the main drag of the city.

Let’s start with what I think is always the most important thing to check out first: the food. Restaurants line both sides of Main Street, and I made a list of the ones I wanted to check out while I made my way to my hotel on the first day. Some of my favorites include Campeche Restaurant for Mexican and margs, Fritz and Frites for some of the best German and French food I’ve ever had, and Little Tokyo makes for the perfect sushi lunch spot right off Main.

Out of all the places I ate, Fritz and Frites was definitely my hands down favorite. I started my meal with a delicious glass of red wine and their mussels, a full order—of course, and knew I had made the perfect decision to eat here on my last night in town. The staff was all incredibly welcoming, and we spent a bit of my time there chatting about the Wine Festival that I was in town for—more on that later. I went on to order their special of the day and naturally rounded out the meal with dessert. If I was a local it’s safe to say I’d be eating here at least once a week.

Everything you could want to check out in Galena and then some is nestled perfectly on the main drag of the city.

Being the Kentucky boy I am, I had to seek out the local brewery and distillery. Any weekend trip without a visit to one or the other isn’t nearly as fun. Galena Brewing Company and Blaum Bros. Distilling Co. were staffed with incredibly knowledgeable folks that I found myself sitting at the bar talking with for hours.

When I first began to look into what I wanted to check out while I was in Galena, Blaum Bros. Distilling Co. was one of the first places that I stumbled upon. After checking it out a little further and reading a bit more about what they distill, I knew I had to make it a priority to stop in. And I’m definitely glad that I did. The space was filled with families, a bachelor party and a few other out-of-towners sampling the wares. I started off with a whiskey flight because that’s what you do when you’re from Kentucky, and then made my way onto trying out a few of their craft cocktails—all expertly crafted.

Now if you’re into the outdoors, Fever River Outfitters is everything you could want and then some. I rented an e-bike to cruise around town one morning and really wish I‘d had time to rent a kayak and get out on the water. Next time though, for sure.

While I was riding around, I stopped at both the Ulysses S. Grant Home State Historic Site and the Elihu B. Washburne House State Historic Site. I’m a big history nerd so getting to learn a little more about the town’s past was the perfect way to spend a Saturday morning.

Galena also boasts an impressive number of events that ensure locals and visitors alike keep busy and enjoy all that the town has to offer. I was lucky enough to be in town during the Galena Wine Festival where I was able to sample several wines from throughout the region, listen to some local bands and enjoy that smaller town life for the weekend.

In typical summer festival fashion, the festival grounds were perfectly situated in a local park by the Galena River. After getting my bearings and scoping out the wines that caught my eye I began to sample several local wineries like Galena Cellars, Massbach Ridge Winery, and Creekside Vineyards. My favorite, though? August Hill Winery. Their blush and rosé selections were perfect for the warm weather and were something I could easily see my friends and I drinking back home by the pool.

Galena makes for the perfect weekend getaway for a group of friends, a romantic getaway, or just a solo trip. So next time you’re thinking of the best place to get away for a bit, I’d highly recommend checking out Galena Country. Even as a tall, tattooed, member of the LGBTQ+ community, I felt right at home in Galena and felt welcomed by locals at every establishment I visited. That’s something that’s become more and more important to me over the years, especially when traveling solo.