Why We Adore Galena, IL

Combine history, romance, and a happy step goal and what do you get? Probably a few different things, but we like to say, Galena, Illinois. As one of our favorite places to frequent in Illinois, we can confidently say this spot has got what it takes to win the ideal date-weekend award every. single. time.  

Pretend it’s Friday night—you just poured your second glass of wine and finally convinced your partner to watch a hallmark movie with you (because ‘tis the season, and why the heck not?). The movie opens as a couple blissfully strolls through the streets of a small, festive town right around Christmas time—warm light floods the streets from the storefront windows and you can almost smell the fresh popcorn in the shop they pass…

(This is us in the street in Galena a few weeks before Christmas)

This is the best way we can describe Galena in the winter time. It truly feels like a scene straight out of a cheesy hallmark movie, which is why we like to visit in the winter, exclusively. Not to discriminate against summer-Galena though, because your smartwatch will thank you for your met step-goal. The Downtown Galena Strip is full of shops that will take you all day to walk, and I don’t blame you if you prefer a 75 degree breeze to a load of snowflakes in your hair. However, you can’t beat the atmosphere of a fully lit street of icicle lights on a snowy day as you pop into shops for warmth and Christmas music. But, we’ll let you decide. 

Why do we go to Galena? For one, it’s a one-tank trip from our hometown (Peoria, IL). Two, the slow pace of the city makes it easy to connect and really just enjoy being together as a couple. 


Places to Stay

The first few times we stayed in Galena, we rented an Airbnb called Miss Kitty’s Cathouse Suites, a small suite of studio apartments right above The Grape Escape, a snazzy cocktail bar with live music most weekends. There are a few suites available, but The Johnson was our favorite.

What we liked about The Cathouse: 

  • It’s right on the strip, so we only had to park once when we arrived and could walk everywhere the rest of the weekend. 

  • The bar below (duh). We could hang out late into the night and just pop right back up to our room when the zzz’s started setting in. 

  • The rooms are modern, trendy, very clean, and the bathrooms were incredible (we’re bathroom freaks, and we’re not ashamed).


But what if you don’t want to stay on the strip? The unfortunate truth is, any place right on the main drag is going to be ridiculously more expensive than anything even right outside of downtown. Which is why we’ve stayed in Dubuque, IA as well. It’s about 20 minutes from Downtown Galena, and you can find some gorgeous spaces to stay for a much better price. We recommend this beautiful downtown apartment with a gorgeous industrial / mid-century modern design style (especially if you’re bringing another couple along). It was hands-down our favorite Airbnb we’ve stayed at in the midwest! 


Shopping on The Strip

If we listed every shop we love, or think you’ll love for that matter, this post length would start getting a little ridiculous. So, we’re going to list a few favorites, and call out a couple that really stood out to us instead!


Rob’s Favorite Shop: Root Beer Revelry

The Vibe: Old-Fashioned | Grandma’s Kitchen | Nostalgic

What we loved: 

  • This sweet shop carries a large selection of unique root beer, everything from nostalgic classics that you drank as a kid, to new flavors you’ve never tried before—shelves upon shelves of glass bottles to choose your favorite flavor from.

  • They offer root beer samples, as well as a tap to pour from if you’re really getting into it. 

  • You can also order a classic root beer float with your choice of unique rootbeer—perfect to cool off with if you’re visiting in the summer!



Madison’s Favorite Shop: Editrix Row

The Vibe: Chic | Cozy | Inviting

What we loved: 

  • This small boutique carries modern women’s clothing styles at a reasonable price. Several other boutiques in Galena can feel less on-trend and incredibly overpriced, in our opinion, but Editrix Row checks the box of chic contemporary clothing at a cost you might be more willing to pay. 

  • The clothing selection is different each time we visit, so there’s always a new style to shop! 

  • The staff is very kind and helpful every time we stop in. 


There’s so much more…

The food scene is a whole other story. Check out our favorite Galena restaurant reviews here.


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Top Restaurants to Visit in Galena, IL

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