Four “Must Do” Galena Activities

I’m embarrassed to admit that it took me almost 35 years of living in Illinois to truly explore one of its travel gems, Galena. Not only is it a scenic and short drive from Chicagoland, it also is a gorgeous place to unplug, unwind, and enjoy the beauty of the Midwest. One of the absolute BEST parts about visiting Galena? You will have a blast either with or without kids. Here are my picks for four “must do” Galena activities:

Get to know grapes

Yes, I’m serious…you CAN take your kids to a winery. Your dog is welcome too, as long as you stay away from the vines and keep Fido on a leash. Or if they are at home being well cared for while you get some time away, explore vineyards through their informative tasting rooms and tours. I highly recommend enjoying some local artisan cheese in addition to the delicious wine in the courtyard or on the expansive porch of Galena Cellars. You can also visit their downtown location if you are looking for wine themed gifts and trinkets to browse while sipping on some of the best reds and whites in the area.

Eat your heart out

One of my favorite things about traveling is trying out the local cuisine. No trip to Galena is complete without a stop at Fried Green Tomatoes, where you will find the best service and tastiest dishes in the area. The De Soto House Hotel, Illinois’ Oldest Operating Hotel, is a great place for a bite or drink while shopping on Main Street, or for an upscale meal at either Generals’ or the Courtyard Restaurants. I would skip Vinny Vanucchi’s and instead head to Cannova’s for delicious Italian meals.

Take a ride

Learn all about Galena’s history, including its close ties to US President Ulysses S. Grant, aboard one of Galena’s Trolley Tours. It is a great way to take in the area and let someone else do the driving along the long and winding roads. There are tours specifically geared towards history buffs and those who are looking for a bit of spooky fun. Depending on weather conditions, you can also take a hot air balloon ride over majestic Jo Daviess County. You can also rent bicycles, kayacks, paddle boards and other types of sporting equipment (even snow shoes and cross country skis if you are brave enough to handle the cold) to explore the area.

Play all day

There are a variety of different fun activities for visitors of all ages. Eagle Ridge Resort and Spa is a perfect spot for those who love the links, as well as those who would prefer to spend the day at the spa. If you are looking for something more fast paced, head over to Chestnut Mountain Resort any time of year. During the winter the slopes can be a heart pounding challenge, and they provide thrills even in the summertime when alpine slides are set up. The resort is also home to “The Soar Eagle” zip line and a min-golf course. Finally, if you want to bring the fun home with you, a trip to Galena isn’t complete without a visit to its popular toy shop, Poopsies, that has the perfect gift for everyone on your list.

Looking for other local getaways? Check out my tips for travel destinations and tips for busy Chicagoland families like mine!

Bon Voyage!


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  1. robin rue says

    Galena sounds like a fun place to visit. I have never been to Chicago or anywhere in Illinois for that matter. Hope to get there someday.

  2. candy says

    I have been to Galena many times and love to go at different times of the year. Halloween and 4th of July are my two favorite times to visit. Love taking the tours, wandering around the unique shops. Hubby loves golf course.

  3. Paula Bendfeldt says

    The next time I’m in Chicago, we have to go visit there, Galena looks beautiful. Isn’t funny, no matter how long we have lived in a place, there is always someplace new to explore. Thank you for sharing with us.

    • Amanda says

      Chicago and Galena are on opposite sides of the state, but both are wonderful for a variety of different reasons. I love slowing down and relaxing in Galena while Chicago is work time for me!

  4. Jeanette says

    How did I not know this was in Chicago area? I obviously need to do a lot more exploring out there! This would be fun to do with the whole family.

  5. Katie Kinsley says

    I would love to get to know all the grapes and the wines at galena. The trolley would be a great way to get around and see the vineyard. There is something just like this in Door County, Wi.

  6. Jill Robbins says

    Everything looks like so much fun! I’ve never heard of Galena. I used to live in the Belleville area, which is waaaay far away from Chicago. I love Illinois and hope to visit soon.

  7. Censie Sawyer says

    Well it looks like we need to take a trip. This looks like a perfect place to have some fun with the family. And your pictures are amazing. The Trolley is something my kids would love!

  8. Eloise says

    I must take a drive there to check this place out! I love the photos, seems like a great getaway to have some fun! thanks for this new adventure ; )

  9. Sandy N Vyjay says

    I have not been to Galena yet. These are some super fun activities we can do with friends and family at Galena. I will keep this in mind when I visit Galena.

  10. Catvills says

    Galena looks like a fun destination. It does look like there are lots of activities to enjoy in different places in Illinois. I hope to get there someday!

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