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.

7 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 just 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

Which 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.

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

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 love visiting places that have 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 on their outdoor space.

Another popular stop is Galena Cellars Vineyard & Winery. We drove out to their vineyard, but I didn’t feel like they’re 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. This is one place we didn’t have a chance to visit but plan to for next time. They distill and produce different spirits, you can do a distillery tour or just enjoy their cocktail bar.

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. When we were there we saw several people fishing, so that’s another option if that’s something you enjoy.

7. Drive to the overlooks

For some cool 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 can 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 book 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.

If you’d rather go with a hotel, check out some of Galena’s best options on 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 in order to allow for 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 meatloaf and it was delicious. I would skip the lasagna. 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 their own 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. We wanted to try Big Bill’s Sandwich Shop & Coffee Bar for their breakfast sandwiches, but we were too late for their breakfast menu (typical us). So next time we’ll try Big Bill’s and report back. 

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 kind of 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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  • Reply Krista September 12, 2020 at 5:45 pm

    This looks like such a cute town to visit! I would love to stop by here on a road trip for a few hours.

    • Reply Lily September 13, 2020 at 12:38 pm

      Hope you do! It’s a charmer.

  • Reply The Fearless Foreigner September 12, 2020 at 4:09 pm

    I went to Galena, IL last summer. It is a really quaint town. Your post brought back a lot of fond memories. I didn’t know about Thunder Bay Falls though. I will have to add that on my list for the next time I visit.

    • Reply The Fearless Foreigner September 12, 2020 at 7:26 pm

      Also I should have asked this first time, but are the stores and museums open now? I know you mentioned an accommodation recommendation and the extra dining, but was just wondering what other indoor places were like now?

      • Reply Lily September 13, 2020 at 12:38 pm

        Yes, most everything seems to be open now including stores, museums etc. They also have indoor dining (limited) if that’s an option you’d like.

  • Reply jackiebrowngately September 12, 2020 at 12:57 pm

    These are some great ideas! I would welcome any one of them but must admit, the wine tour tops my list.

    • Reply Lily September 12, 2020 at 1:38 pm

      Hahaha same!! Photos and wine all day please!

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