Wow, I think this is the longest in a year we’ve gone without a vacation of any sort! With three quarters of a year down, after all the hard work and hustle, Brett and I finally got away for a long weekend. We wanted to go somewhere where we could drive to within 5-6 hours, possibly somewhere we haven’t gone before. So, after getting recommendations from friends, I planned for Galena, IL (3 hour drive) and booked our AirBnB home in Dubuque (just 25 minutes from Galena, just on the other side of the Mississippi River.)
I’m obsessed with AirBnB, especially going to smaller cities and country areas, because I book beautiful country homes and farms (especially, if they are horse properties!) This is the third farm property we’ve stayed at (Nicholasville, KY and Nashville, TN prior to Dubuque) . I’m very happy Brett goes along with it, because while it’s MY dream, country living is not his preference. If you’re ever interested in an experience like the one I’m about to talk about, use my AirBnB referral link for $40 off your first booking!
Guys, our trip was only THREE days, but felt like a week! Usually when something feels like a long time, that means it was dragging on, but this was quite the opposite. We did so much, and each town we spent time in was very different from each other.
Here is the recap of our trip:
Day 1 Friday:
Picked up the rental car, packed up, headed out at noon. Went to the Anderson Japanese Garden and ate an early dinner at The Olympic Tavern in Rockford, IL. Headed out to our AirBnB farmhouse, arrived in Dubuque, IA at 7pm. Settled in, met our host and toured the property. We just lounged around for the rest of the night, since we were tired from driving.
Day 2 Saturday:
Woke up around 7am, made coffee, went out to greet the horses and take photos. Went to breakfast downtown at Caroline’s Restaurant in the Julien Hotel at 9am. Walked around the different Dubuque districts (Town Clock, Historic Millwork, Upper Main, and Cable Car Square). Took the Fenelon Place Elevator where you can see the tri-states from the top (Iowa, Wisconsin, and Illinois.) Happened upon Bloktober Fest in the Millwork District (music, beer, skateboard & bike ramps).
Went to Galena, IL where their Oktoberfest was going on, watched the Weiner Dog Races, then went to Main Street for the shops and bars. Left Main St. to go to the Blaum Brother’s Distillery around 6:30pm. Had a delicious dinner back in Dubuque at Brazen Open Kitchen around 8:30pm, then headed back to our AirBnb around 10pm, where I took a much needed Epsom salt bath before passing out.
Day 3 Sunday:
Woke up around 7am (our brains don’t seem to want to sleep in much.) I took more photos before we packed and cleaned up for check out. Left at 10am for brunch at Timmerman’s Supper Club in East Dubuque. Went to the last Dubuque district, Port of Dubuque, and walked the Mississippi Riverwalk (about half a mile each way.) Grabbed some coffee at Jitterz, tea at Inspire Cafe, and headed into Galena one last time around 2:30pm. Walked Main street, climbed the Galena High School Steps project (my legs hated me), then had a snack at the Galena Brewing Company. Around 4:30pm, stopped really quick to see Thunder Bay Falls for some photos. Finally, we drove back home to arrive at 8pm.
Overall thoughts and conclusions:
Brett and I both went into this weekend excited to see all the boutiques, wineries, history and scenery that Galena has to offer. I’ve been to Galena, once before in 2013, for my friend’s bachelorette party, and it was fun! Even though I don’t drink (can’t handle it so I just don’t anymore), it was such a cute town to visit. We got our nails done, ate good food, window shopped the boutiques, and a few bars. The Perfect Girls Weekend. This town is still known for hosting many girls’ weekends and bachelor/bachelorette parties.
When we went, it was not only crowded because it’s one of the top 10 best Small Towns in the US, Oktoberfest was going on as well, so it was a little rowdy. I actually found myself overwhelmed by the number of boutiques and bars, and I had a hard time finding things I wanted to buy (and that is RARE for me! I only bought a super comfy sweater that says “I just want all the dogs” and that’s not even that unique LOL) What I did love was that the businesses in Galena are all small businesses. There was not a single chain or franchised business. There are long-standing businesses to add to the history of the town. So, in general, Main St. is definitely a very touristy stop for visiting friends & family, and with the number of bars/wineries/distilleries, a fantastic place to drink. The 19th century buildings, natural parks, and overall scenery is worth the visit, so I recommend to visit at least once in your life!
Dubuque, Iowa. I had no idea what to expect. I just know I love the countryside and farm life. I had no idea how much we would end up loving the city! The Millwork District has so many re-purposed industrial buildings into restaurants, boutiques, yoga studios, coffee shops, and more. The Port of Dubuque has the Mississippi Riverwalk, which is perfect for the history and views of the largest river in the US. The Fenelon Place Elevator was so cool! It is the world’s shortest and steepest railroad, and you sit in this cable car that carries you almost 200 feet from Fourth Street up to Fenelon Place. From the top, you can see three states (Iowa, Wisconsin, and Illinois), and the Dubuque historical business district. There were so many good cafes, restaurants, and shops! Our food/drink spots were breakfast at Caroline’s Restaurant, coffee at Jitterz, tea & beer at Inspire Cafe, and dinner at Brazen Open Kitchen. It was not a crowded city (which, the introvert in me loves that) with easy to find parking and very inexpensive parking rates, if at all. Coming from Chicago, all of those things are huge pluses! The Street Art Dubuque was so cool to see! There were many wall murals throughout the city and I found all but one of them!
Talk about a packed weekend! It was really nice to get away though, with a change of scenery, new people, new restaurants, and a new vacation spot to revisit!
I hope you enjoyed this weekend recap! Let me know if you visit any of the spots I mentioned above!
HW Life & Style 
Awesomeness !!!!! It looks so calming and peaceful. I’ve always wanted to rent an Airbnb I’ll use your link!
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