7 Fun Things To Do in Galena, Illinois: The Perfect Chicago Road Trip

With its rolling hills and incredible charm, Galena is a unique town located in Northwest Illinois. It’s filled with 19th-century architecture, antique shops, wineries, and everything else necessary for a relaxing, fun getaway.

And yes, rolling hills exist in Illinois! I had no idea! Did you know that almost 90% of what is now Illinois was affected by glaciers several times throughout history, and that’s why it’s so flat?

The part that wasn’t affected is where Galena sits. This is why that area is beautifully unique. Honestly, at times the drive reminded me of Tuscany.

Fun Things To Do in Galena

I know this year has been nuts, and traveling has been especially difficult for many. However, getting away, even just for a few days, can work wonders for your state of mind. So this is why I’m sharing 7 fun things to do in Galena, Illinois, regardless of your travel style.

Being only 3 hours away from Chicago, Galena is the perfect weekend road trip. I’ve lived in Chicago my whole life, and I can’t believe this was my first time visiting.

I just never realized how charming it was or how much it had to offer. Needless to say, Galena is a nice escape if you’re from a big city. I’m sure the town will impress you and have you planning a trip back.

1. Experience Galena’s historic district

This is always my favorite thing to do anywhere I visit, so of course, I’m listing it first. Grab your camera and head onto Main Street to capture the town from all angles. Since Galena is hilly, you’ll be climbing a few steps during your trip. But this always makes for great photos since you’ll be able to see the town from different altitudes.

There’s plenty to see on Main Street (which is flat), but if you want to venture out, start climbing the steps to see other parts of town. You can visit the home of Ulysses S. Grant, walk over to the Belvedere Mansion, or check out my new favorite park in the world- Grant Park.

2. Find Peace at Galena Grant Park

This brings me to number 2; Grant Park is impressive! I love that it sits across the river from Main Street and allows you to see a lot of Galena’s charm from a park bench.

I have this weird obsession with trees, and Grant Park is filled with beautiful mature trees that provide plenty of shade for hot summer days or plenty of colors on crisp fall days. UPDATE: We went back to Galena in the fall, and the colors were magical! It’s hard to time it right, but I stalked everyone on Instagram to get an idea of when it was peaking.

Summer photo:

Fall photo:

We were only in Galena for two days during our summer trip, but J and I would buy coffee and walk over to the park to sit on a bench and take in the view each morning.

Those were some of the most peaceful mornings I’ve had all year. I felt like I could sit there for hours.

I don’t usually care for hanging out in parks, but this one was perfect, and I wanted to put it in my pocket and bring it back home.

3. Visit Galena’s Wineries and Vineyards

Since I started liking wine more (I blame Germany’s Riesling), I have loved visiting places with vineyards that offer wine tastings. As you can imagine, there aren’t many in Illinois, but Galena is a good spot for it.

You’ll find a handful of wine bars on Main Street, but the town also offers two vineyards that you’ll need to drive to and two more that are in nearby towns. You’ll also find a distillery and breweries.

My favorite one was Fergedaboudit Vineyard & Winery (where all these vineyard photos are from). Due to the pandemic, they’re not offering wine tastings, but you can buy flights of different wines to enjoy in their outdoor space.

Another popular stop is Galena Cellars Vineyard & Winery. We drove out to their vineyard, but I didn’t feel like they were doing a good job managing the process during this time. I would visit their wine bar on Main Street instead. If you have time, check out Massbach Ridge Winery or Rocky Waters Vineyard and Winery in the nearby towns.

If you don’t like wine, you can check out Blaum Bros Distilling. They distill and produce different spirits; you can do a distillery tour or enjoy their cocktail bar. This is one place we didn’t have a chance to visit but plan to for next time.

4. Kayak down the Galena river

If you prefer a little more adventure, you can rent kayaks and make your way down the Galena River. You can also rent bikes, tandem bikes, or book tours here. If you drive out to Chestnut Mountain Resort (about 20 minutes away), you can zipline, go down a huge alpine slide, or ski if you’re visiting during winter. Plenty of options for the active folks!

5. Take a historic trolley tour

The trolley tours look fun, and I’ve heard great things about them. We didn’t get a chance to do one this time around, but it’s on our list. It’s a good way to get a feel for Galena and learn more about its history, all from the comfort of a trolley.

6. Visit Thunder Bay Falls

Add Thunder Bay Falls to your itinerary when driving to the overlooks (more below) or visiting the wineries. It’s only 11 minutes outside of Galena and a great photo spot. We saw several people fishing when we were there, so that’s another option if that’s something you enjoy.

7. Drive to the overlooks

For some excellent views of hilly Galena, drive over to the following overlooks:

Long Hollow Scenic Overlook– Located along the Great River Road on U.S. Hwy. 20. You can pull over to get some photos.

Horseshoe Mound – Spend a few minutes to hours there relaxing. You can even bring your own picnic! Tables are available.

If you don’t feel like driving, you can get beautiful views of the town from different angles. Some of my favorites were from the main pedestrian bridge crossing over to Grant Park, and of course, the views from the park are also gorgeous.

If you make your way up to Ulysses S. Grant’s home, you’ll get lovely views of the town from a higher point.

Where to stay in Galena 

With the pandemic happening, I was looking for a place that was transparent about their cleaning and safety protocols and where I could minimize the exposure to other people.

Greenbriar Country Inn and Suites ticked all those boxes, plus they had great reviews and were affordable. They even go the extra step of leaving rooms unoccupied for 48-hours between guests.

Greenbriar is a bed & breakfast, but they only serve breakfast on weekends (that’s how they keep pricing low on weekdays). I didn’t mind this since I like trying places around town for breakfast.

I believe they have “standard” rooms and “suites” in 2 different buildings. Some of the rooms have private entrances, and that way, you can completely avoid running into anyone else indoors. Those private entrance rooms are #6, #7, #9, #10, and #11.

You can book your stay with Greenbriar by contacting them directly on their website. You can also reserve specific rooms through Airbnb.

We stayed in room #9 linked here, but with a quick search, you can find all the rooms they’re hosting. Our room was spotless, came with free parking and a fireplace! They show up as “superhost” on Airbnb, which is always a good thing.

UPDATE: During our second trip to Galena in the fall, we stayed at this fantastic bed & breakfast called Aldrich Guest House. We only had one night there, but the hosts were the friendliest. The house was beautiful and full of history, and it included breakfast and a delicious happy hour (the first fancy cocktail is free).

I loved our stay there so much! They were also taking all the covid precautions and had plenty of space to spread the guests out. I felt safe and would stay there again.

If you’d rather go with a hotel, check out some of Galena’s best options on Booking.com.

Booking.com

Where to eat in Galena

I’m not sure how it’ll be going into winter, but currently, Galena has closed parts of Main Street to traffic to allow more outdoor dining. It’s much better spaced than it appears in this photo.

Fried Green Tomatoes– I was surprised by how much I liked this place. They give you freshly baked bread to start, and it’s so fluffy and good. I ordered the meatloaf, and it was delicious, and honestly, the main dish that I keep going back to every time I visit. Both of our entrees came with a salad and a homemade dressing that was also really good. It’s a great choice for dinner. 

Little Tokyo– If you’re in the mood for sushi, this is a good spot. I would skip the hibachi dishes. They do have an outdoor patio so ignore the fact that Yelp says they don’t. 

Otto’s Place– We went to Otto’s for breakfast, and it wasn’t anything special. It wasn’t bad, but not a place I’d recommend. After several trips back to Galena, we can confidently say a good breakfast restaurant is necessary. 

Trolley Depot Coffee & Tea Company– I’m so happy we had Trolley Depot! Visiting cafes is such a special part of our travels, and when a town doesn’t have anything good, we’re disappointed. Trolley Depot is still pretty new to Galena but a great addition. Based on reviews it is the best cafe in town. We agree the coffee was excellent, and it kept us going back. They also have coconut and oat milk alternatives.  

If you’re driving in from Chicago during spring or summer, try to stop at Three Sisters Sweet Shoppe for ice cream in Elizabeth, Illinois. It’s the cutest little shop, and they have good reviews. We tried visiting, but they were only open on weekends. I just checked their website and saw that they’re now closed for the season. They’ll reopen next spring!  

There ya have it. Galena is so small yet exudes charm and has so much to offer. I’m planning a quick trip back for the fall foliage! If you’ve been to Galena, let me know what your favorite thing to do is in the comments below.

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