I can’t believe we are already into July! I hope everyone had a fun 4th of July weekend. My husband and I went to Galena for the long weekend and had a wonderful time. As a semi-local Galenian (my parents have a place there and we go a few times a year), I wanted to share my favorite places and things to do there. If you are local to the Chicagoland area it is the perfect getaway town outside the city!
We were there Wednesday to Sunday but you really can do everything in a shorter weekend trip. Galena is about a 3 hour drive from Chicago. It is home to a lot of old pre-Civil War history, antique shopping, and some great golf courses (my husband and dad did a little golf outing while we were there). It is becoming quite the getaway travel destination so in addition to having a lot of nice hotels, there are some really spectacular BnBs and Air BnBs. The Jail Hill Inn and the Aldrich Guest House have both won awards for being some of the top BnBs in the nation. While there are a lot of nice places to stay outside of town, I would definitely recommend staying close to downtown Galena unless you want to prioritize golfing. It is not an Uber accessible town and some of the shuttle services are rather limited.
What to Do
I have been to Galena so many times that I haven’t done the more historical attractions in awhile. If you are into Civil War era history, I recommend researching some of the museums and history the town has to offer. You probably know by now my speciality is shopping and martinis (lol) so I’m going to share more of that here:
Shopping in Downtown Galena
I go to Galena to shop (and relax of course). It is a blessing and curse that unless you are in a place with wi-fi it is impossible to get good cell service downtown. The main stretch of downtown Galena is not very big, but packed with unique shops. I feel like every time I go a new store has opened that brings it’s own flair to town. The Hideaway Home & Goods just opened and it was fun trying out the different perfumes and seeing the vintage decor and jewelry. They also had some fun astrology themed goods!
My must have stop-ins for shopping include:
- Carlotta’s Studio, Elle & Beck’s Lifestyle Boutique, Editrix Row, Lulu’s Too, and Simply Elegant Boutique for clothes.
- Grateful Gourmet, Galena Canning Company, Galena Garlic Company, Galena River Wine & Cheese for amazing food goods to take home (or eat on your trip)! The canning company has my favorite mustards, sauces and olives (for martinis, obviously). On Saturdays a lot of places have samples which could almost suffice as a second meal. The garlic company and the wine & cheese shop also have a huge assortment of olive oils and vinegars to try. Flavors I bet you didn’t know existed come in the form of balsamic vinegar and olive oil, and they are actually really delicious.
- Other fun shops: Poopsies (don’t ask, just go; guarantee you will find a gift there for someone), Great American Popcorn Company (again – any flavor of popcorn you want, they have), Galena River Goods, Galena’s Kandy Kitchen, and Galena Book & Paper Co.
- There are so many decor and antique shops and art galleries featuring some amazing artists. I wish I could list them all!
Where to Eat & Drink
Galena is not short of wine, cocktail bars and restaurants. Usually when we come here we rotate between a few spots for lunch and dinner. For breakfast we love going to Otto’s Place and the Galena Bakehouse (my husband is obsessed with their empanadas).
Lunch & Dinner:
My favorites are listed below and all are linked!
- Log Cabin Steakhouse
- Fritz & Frites (the best german chocolate cake I have ever had)
- Fried Green Tomatoes
- Vinny Vanucchi’s Little Italy
- Frank O’Dowd’s Irish Pub & Grill
- Big Bill’s Sandwich Shop & Coffee Bar (lunch only)
- Durty Gurts Burger Joynt
Cocktails & Wine:
My true wheelhouse, wine and cocktails. We are Galena Wine Club members. I highly recommend going to the Galena Cellars in town or to the vineyard for a tasting. The vineyard is about a 15 minute drive outside town. It is super cute. You can buy charcuterie and sit outside there or. Just a warning, unless you are a super sweet wine person (which I am not) stay clear of anything super fruity. They are known for having some sweet wine flavors but the drier wines are very good as well.
In my opinion, the best martini ever is at Miss Kitty’s Grape Escape. They have a huge cocktail and wine list as well, but their dirty martini is incredible (they also have hand stuffed olives). The cocktail bar is a fun vibe and a hot spot. They have live music all weekend and it’s usually hard to get a seat on busy weekends.
There are some other cute local wine and cocktail spots. We love Champagne on Main and the Galena Brewery as well. Blaum Bros. Distillery just opened a tasting room and bar in town and we checked it out for the first time last weekend. It has a little more of a dark, speakeasy vibe which was very cool.
Until Next Time…
I’m probably missing a ton of other Galena content but you get the idea. One of the things I love about Galena is that there is always something going on, even in the winter. Summer is jam packed with events but the fall and winter also have fun happenings and the town stays lively all year. I hope you enjoyed this little lifestyle piece! Back to some regularly scheduled makeup content next week!
Martinis & Mascara 
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