Just a three-hour drive from the bustle of Chicago is quaint little town, nestled between corn fields, with a down-to-earth vibe. Galena, voted as one of the top 10 small towns in the United States, offers respite from the big city with its winding country roads, independent downtown shops, and picturesque homes along the river. It’s a charming place, where the pace of life seems slower and the air seems crisper; fresher.

Galena Illinois along River

We (the Passion Passport team) traveled to Galena in mid-September as part of partnership with Enjoy Illinois. Though our time there was limited, we managed to get a wonderful taste of much of what the town has to offer, from food to vespa rides to historical architecture. It proved that no matter how much time you have – be it a day, a weekend, or a whole week – Galena is a wonderful destination for a getaway in Illinois.

Here are some of our recommendations. Let us know some of your local favorites by leaving a message in the comments section below!

To Eat:

Wander along Main Street for a plethora of dining options, from sandwich shops to Mexican eateries to upscale steakhouses.

For barbeque lovers, try Chef Ivo’s place; the restaurant has been a town staple for over 20 years. Their sauces are bottled and sold in some of the local shops as well, so you can be sure to take the flavors home with you.

For dinner, try Log Cabin Steakhouse; it’s Galena’s oldest restaurant dating back to 1937 and offers typical steakhouse fare with a Greek twist. The bar area makes you feel like you’ve traveled back in time to an era of righteousness and indulgence; think dark wood, soft music and fancy cocktails.

For breakfast or brunch, try Otto’s place. The restaurant is across the river that runs parallel to Main Street, at a comfortable distance away from the more crowded streets of downtown. To get there, you’ll have to wander through a pleasant residential area; exploring the neighborhood adds to the experience.

Galena Illinois Passion Passport Team

To Do:


From bike rides to kayaking to wine tastings to historical walking tours; Galena offers a wide range of activities.

Fever River Outfitters is a great place to start should you want to plan an outdoor adventure. They offer paddleboard, kayak, canoe, and bike rentals; in the winter, snowshoes and cross-country skis are available.

Our Passion Passport team opted for scooter rentals and went on a 45-minute drive down country roads and through expansive corn fields to the Galena Cellars Winery. This vespa adventure quickly became a highlight of our time in Galena; it was exhilarating to ride amidst the beautiful scenery, past small white chapels and grazing horses and sprawling farmland. When we arrived at the winery, we were treated to a sampling of local wines. We found a table in the sunshine outside, grabbed some cheese, meats and other spreads, and indulged in an afternoon feast. The folks from Fever River Outfitters picked us up at the day’s end, so we didn’t have to worry about driving our scooters back after the tasting.

Galena Illinois Passion Passport Team

For those who are not up for outdoor adventures, there is still plenty to do in the town. Hop on the Tri-State Trolley for a ride through Galena’s historic neighborhoods and check out some of the architecture dating back to the 1800s. Walk up to Quality Hill, taking the same steps President Ulysses Grant did over two centuries ago. You can climb the Old Firehouse Steps (over 200 of them) or the Green Street Steps (149). At the top, you’ll be rewarded with a beautiful panoramic view of the city.

Looking for an even more relaxed trip? Stroll up and down Main Street and stop in many of the small, independent shops that line the drag. When it’s time to rest your feet, visit one of the local coffee shops (we loved Rendezvous Coffee and Tea’s tranquil vibe).


What are some of your favorite spots in Galena? Any other great recommendations for a weekend getaway in Illinois or the Midwest? Do share in the comments section below; your suggestion could be our next destination!