A couple weekends ago, a few girlfriends and I packed our bags and headed to Galena, IL for a little weekend getaway. Galena is only about a 2.5 hour drive from Chicago, making it the perfect destination for a weekend trip.
Galena, IL is known for its quaint little downtown and wine. There are multiple wineries surrounding Galena, so if you are a wino this is the place for you!
I loved visiting Galena in the fall because it is SO PRETTY! The rolling hills and farmland with the most stunning foliage is the perfect backdrop as you sip on wine all day long.
The perfect comparison to Galena is Stars Hollow from Gilmore Girls. It is so cute and quaint! Galena has so much character for such a tiny town.
Where to stay
We stayed on the outskirts of downtown in an Airbnb. There are so many Airbnb options to choose from. From farm houses, to log cabins to tree houses, there are plenty of airbnbs for all likings.
There are a number of hotels and bed and breakfasts right in town as well. The Desoto House is one of the fancier options. But beware it is extremely haunted!
We enjoyed our airbnb a lot! It had a gorgeous view of the trees and farmland. It was the perfect backdrop for our apple cider mimosas in the morning!
What to do
A weekend is the perfect amount of time to stay in Galena. There is not a ton to do, but still enough to keep you busy.
Galena Wine Cellars and Vineyard
The first thing is wine, wine wine. We spent the majority of the day at Galena Wine Cellar and Vineyard. There was live music on Saturday and we enjoyed wine flights. I had the fall flight which included an Oktoberfest wine, apple cider wine, and cranberry wine. It put me in the fall mood. Due to the pandemic, they are not offering tours or tastings, but you can grab a table outside, bring stuff for a picnic and enjoy a beautiful fall day.
Like I said there are a few other wineries around the area, but they are about 20-30 minutes from each other. But each winery does have a tasting room downtown. So we were able to try all the local wines during our stay!
Matthew’s Haunted Pub Crawl
If you know me, you know that I love ghost tours. I have been on them all over the world and this girl’s fall getaway was the perfect time to go on one. Galena is pretty haunted believe it or not! We decided on Mathew’s ghost tour because it was a bar crawl. We stopped at 3 different bars for drinks while he explained the history of ghost, and the hauntings of Galena with a ton of personal experiences and stories sprinkled in. It was so much fun to do this spooky activity!
Shopping
Main Street is full of mom and pop shops. You could spend hours wandering in and out of different shops, and we did! From hot sauce shops to candle shops to boutiques and everything in-between this was one of the best parts of Galena. My favorite shops we visited were:
Galena Goat Yoga
We decided to back out of goat yoga last minute, but this was on our itinerary to do during our trip! It seems like a one in a lifetime experience, but low-key I am kind of freaked out by goats!
Where to eat/drink
I will say, Galena is not that much of a foodie town, it is definitely more of a wine town, but we had some good food while we were there!
Galena Brewing Company
This was our first spot once we got into town. We enjoyed Oktoberfest beers and some cheese curds (since we were so close to the Wisconsin border). They had a nice array of beer and the menu looked good as well.
Durty Gurts Burger Joynt
This place is known for their burgers and they did not disappoint. They also have boozy milkshakes and an extensive drink menu. I loved the ambiance of this casual spot! Would be perfect for lunch or dinner.
Otto’s Place
There weren’t many breakfast/brunch places but after two days of trying to get a reservation, we were able to get a table! It is such a cute little place on the railroad tracks. The food was yummy too! The mimosas were big and the biscuits were hot, fluffy, and buttery. Mine kind of place!
Cannova’s Pizzeria
I really wanted to have dinner at this Italian joint, but it was only open for curbside pickup. It worked out because we were able to pick some up for dinner. We ordered a few pizzas and they were super yummy. I would love to come back and try their homemade pastas!
Other notable restaurants
Since we were there limited time, and due to the occupancy restrictions, we didn’t get to try all the restaurants on my list! Here a few:
Galena is the perfect little getaway if you want a change of scenery for a weekend! The downtown transports you back in time, you are definitely going to find some goodies in the shops, and you will be able to fill up on all the wine your heart desires. Whether it is a girl’s trip, couples getaway, or a family weekend, consider Galena!
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