Taste of Galena, IL
- Lindsay Probasco
- Nov 5, 2019
- 6 min read
Galena- I love you. You beautiful, little town.
Mike and I just got back from a trip to this quaint Illinois gem after a weekend full of fun and adventure with two of our best pals.
If you've ever thought about going and haven't, I highly recommend. In a nutshell, I'm already planning our next trip back.

For a place with one literal "Main Street" (pictured here), we didn't even come close to hitting everything on the list I had made prior to going. Yes, I am absolutely INSANE and make lists pretty much before I go anywhere. For me and my Type A planner personality, it helps give us at least a back bone of what the trip has to offer. Don't get me wrong, we stray from my lists a lot. Whenever we go on our weekend getaways or even big vacations, we always find a few places that grab our attention. These usually end up being some of our favorite stops, whether we stumble upon them or stumble out of them.
While I planned to make the bulk of this post about the food & drink scene, I have to give some background on travel for this. If you're coming from Chicago like we were, be prepared for a bit of a hike. This was a longer driver than we expected, and rush hour traffic on a Friday out of the city didn't help. However, there is pretty much one way out to Galena (located in the northwest corner of Illinois) and luckily there is a hub to stop in at along the way.
Rockford, IL. You also have my heart and my attention. We stopped into this outskirts suburb for dinner at Taco Betty's. From first glance, it looks like a small cozy pub. However, we took this trip the first weekend of November while it was rain/snowing, so any place with a bar might have looked this way to me. In the summer, Taco Betty's has a bumping rooftop with a second menu (we are planning to go back!). As for the first-floor food, this reminded us so much of Big Star in Wicker Park. It's important to note that this is one of our favorite city restaurants.
I ordered the Crispy Fish Taco Plate and Mike had the Chipotle Chicken Taco Plate. Both were FABULOUS! The Chips and Guacamole were awesome as well. The menu is smaller, but everything we tried was great and more authentic tasting than your typical Mex-American joint. As for a cocktail, I highly recommend the classic margarita on the rocks. Check out the restaurant on Facebook to see what's happening: https://www.facebook.com/tacobettys/
We plan to do Rockford as an entirely separate trip next time, because there is so much to do and see there. There are a few breweries, shops and walkable activities all surrounding the Rock River.

Once we arrived in Galena (after what was quite a spooky & dark drive while listening to a murder podcast like I do), we began our stay at the Irish Cottage Boutique Hotel. This place is a dream and will make you feel just like you hopped on over to Ireland. One of the taxi drivers we had over the weekend also mentioned she has all of her family and friends stay there when they visit, so it was comforting to know that even the locals find it absolutely charming. There was live music in the lobby pub (Frank O'Dowd's) until midnight where we had a chance to unwind after a long drive with a few Irish pints. The hotel is covered in all things Ireland from the gift shop to the furniture and artwork on the walls. The rooms were spacious and clean and decorated with Irish family names on the doors and proverbs on the walls.
On Saturday morning, we made our way to the "Downtown" which was about a 5 minute drive from the Irish Cottage. Our plan was to have breakfast at Otto's Place, a Galena staple that I read about time and again. However, we did not call ahead and were told it would be a 1.5 hour wait. While I was excited about the menu, this seemed a bit out of the question for us as we had many places to hit throughout the day. Perhaps I will try again the next trip I make back, but the vibe we got from Otto's was not great. It was certainly a disappointing start to our day.
However, we crossed the river that runs through the town, and came across Victory Cafe. We were told it would be a 30 minute wait here, and felt that was a bit more reasonable. We wandered over to Mean Bean Coffee Roasters while we waited for our table.
The smell of freshly ground beans hits you as soon as you open the door. This place was exactly what we needed to get our day back on the right track! Their menu included all kinds of coffee and a "Make-Your-Own Donut" wall with all the potential topping options. We took our coffee over to the tables and browsed their shop while we got ourselves caffeinated for the day.
When our table at Victory Cafe was ready, we were greeted by amazing staff and blessed with the most delicious Bloody Marys infused with Bacon. What more could you want from a breakfast joint? The food menu was small, but got the job done right for an affordable price. Three of us ordered the "Two Eggs with Meat and Potatoes Breakfast" and Kyle ordered the Country Fried Steak. Everything hit the spot! Overall, we were pleased with our experience at Victory, and would be likely to go back over Otto's and the unwelcome feeling we unfortunately received there.

Next, we browsed a few of the downtown shops on our way to the other end of Main Street where Galena Cellars Tasting Room can be found. The shops of Galena are darling and gave me tons of good Christmas gift ideas that are out of the box. I will definitely be spending more time shopping next time we go back!
Galena Cellars was my favorite part of our day. We had the most wonderful tasting experience (6 tastings for $5) with Kathy behind the counter. She taught us a lot about the wines and told us even more about herself and how she ended up at Galena Cellars. She was a joy to get to know, and I would recommend you ask for her if you go! She let us try a few extra tastings based on our preferences and had us laughing from the second we met her. One of the most interesting wines we tried here was a Jalapeno Infused Wine that can be enjoyed by itself or in a Bloody Mary (both of which we tried). They make a few other fun and interesting wines (like Caramel Apple Wine-hot out of a Crockpot) so it's worth a stop in if you are looking to try both traditional and funky wines.
After this, we headed down Main street to the Galena Brewing Co. where we sat for HOURS. If you enjoy craft beers, this is the place to be. While here, we tried a few different beer varieties, including seasonal beers like Sgt. Pepper which infused Raspberry and Habenero. Surprisingly delicious!

We moved onto dinner at Dirty Gurt's for burgers and boozy buckets. The food was good and the buckets were strong, but we weren't sure this would be a place we were dying to get back to. If you make a trip, you'd be okay skipping this stop. Our original plan for dinner was to drive out to Chestnut Mountain and have dinner overlooking the sunset and beautiful Autumn views at their restaurant called Sunset Grille. We were having too much fun to leave the downtown, but I will definitely make sure to book it for next time!
Giving this Weekend Getaway an LP Wellness Rating of a 6. While the drive was further than we expected, this cozy town and all its charm blew us away. Would recommend to a friend, especially in the Fall for all the scenic colors on the rolling hills. Pair the #views with good coffee, good wine and good friends and you've got yourself a perfect weekend getaway.
Let me know if you've been and if you have any of your own Galena recos. Send me a note below!
xo--
LP
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