Galena, Illinois. Photo via Shutterstock.

Best Things to Do in Galena, Illinois

BY Megan Bannister | July 29, 2021

Welcome to Fifty Grande’s Best of the U.S. Bucket List series. This is your one-stop travel guide to the best, most unique and quintessential experiences of a city, state or event. Want to know how to “do” Galena, Illinois? We’ve got you covered. Curated by experts, vetted by in-the-know locals, this is all you need to have the best trip ever. If we’ve written a Bucket List, we recommend you go. If it’s on this list, it’s the best the city has to offer right now. Consider this your one-stop answer to “What are the best things to do in Galena?”

This story appears in Fifty Grande Magazine #3, the Road Trip issue.

Let me paint you a picture of the perfect fall weekend away. It’s a gorgeous Midwestern day in northwest Illinois. You first think, “Wait, why am I in northwest Illinois?” Then you notice the sun is warming the bluffs of the Mississippi River and the leaves are just starting to change to vibrant reds and oranges. Wandering up and down Main Street in Galena, with all of its shops, restaurants and historic sites, you’re enjoying its classic charm. It’s like something out of a Hollywood lot for a movie set in quaint small-town America. With its perch along Historic Route 20 and 80% of its downtown buildings on the National Register of Historic Places, you know there’s plenty to do. But even a savvy traveler like yourself can benefit from a little guidance to help you find the best of the best. Here are the best things to do in Galena, Illinois.

Opt Outside

See the area’s picturesque views and vibrant fall colors by hiking outdoor spaces like the Horseshoe Mound Preserve and Apple River Canyon State Park, which have scenic overlooks and miles of trails. Galena also has a number of resorts, like Eagle Ridge Resort & Spa and Chestnut Mountain Resort, with ways to enjoy the outdoors including golf courses, ziplining, alpine slides and more. 

 

Horseshoe Mound Preserve
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Beautiful panoramic view looking down to the historic city of Galena in Illinois from the top of Horseshoe Mound with long green grass meadow in the foreground and pink and blue sky beyond at sunrise. Photo by Shutterstock.

Horseshoe Mound Preserve

1679 North Blackjack Road, Galena, IL, USA
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Apple River Canyon State Park
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Apple River Canyon State Park, Apple River, Illinois. Photo by Shutterstock.

Apple River Canyon State Park

Apple River Canyon State Park, 8763 East Canyon Road, Apple River, IL, USA
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See a Piece of Presidential History

If early U.S. history is your cup of tea, you can discover Galena’s presidential claim to fame by visiting the home of our 18th president, Ulysses S. Grant. In August of 1865, Galena welcomed its Civil War hero General Ulysses S. Grant home with a parade and beautifully furnished Italianate-style home. While he was elected president in 1868 and only visited Galena occasionally after that, you can still experience the home as it was in the 1860s today.

 

Ulysses S. Grant Home State Historic Site
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Ulysses S. Grant Home State Historic Site

Ulysses S. Grant Home State Historic Site

500 Bouthillier St, Galena, IL, USA
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Eat at a Classic Supper Club

There’s a reason that supper clubs have been a quintessential part of Midwest dining culture since the 1930s. From hearty portions to homey atmosphere, you won’t want to leave Galena without experiencing this piece of culinary culture. You’ll feel like you should have a cigar in hand when you step into the Log Cabin Steakhouse’s dark wooded interiors to enjoy classic dishes and strong cocktails like an Old Fashioned along Galena’s Main Street. Or you can opt to drive outside of town to Timmerman’s Supper Club, which overlooks the Mississippi River from its blufftop dining room with panoramic windows.  

 

Log Cabin Steakhouse in Galena, Illinois
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Log Cabin Steakhouse in Galena, Illinois

Log Cabin Steakhouse

201 N Main St, Galena, IL, USA
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Timmerman’s Supper Club in Galena, Illinois.
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Timmerman’s Supper Club in Galena, Illinois.

Timmerman’s Supper Club

7777 Timmerman Drive, East Dubuque, IL, USA
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Hoof It

Plan an outdoor adventure with these unlikely tour guides. Hoof It Goat Treks offers hour-long, 1.25-mile hikes through their wooded property with goat (as well as human) guides. You’ll get to experience Galena’s great outdoors while interacting with the goats along the way. Hoof It also hosts live music events throughout the summer and fall as well as a spooky Halloween glow walk through the woods followed by a bonfire and plenty of time for goat snuggles. 

 

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Two goats look at the camera. Photo via Shutterstock.

Hoof It Goat Treks

616 South Devils Ladder Road, Galena, IL, USA
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Pack a Picnic

With artisanal shops of all kinds, Galena is the perfect place to enjoy a fall picnic, so come hungry. Stop by Galena River Wine & Cheese to stock up on all the essentials for a charcuterie board, including cheese, crackers, meats and a picnic-sized cooler if you didn’t bring your own from home. For more involved picnic packing, the shelves at Galena Canning Co. are full of dips and sauces and salsas to make even the most basic sandwich shine. 

 

Galena River Wine & Cheese in Galena, Illinois.
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Galena River Wine & Cheese in Galena, Illinois.

Galena River Wine & Cheese

420 S Main St, Galena, IL, USA
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Galena Canning Co. in Galena, Illinois.
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Galena Canning Co. in Galena, Illinois.

Galena Canning Co.

106 & 107 S. Main St., Galena, IL, USA
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The Spooky Side of the City

If you aren’t afraid of no ghosts, you can embrace the spookiest season with a look at some of Galena’s paranormal places. Amelia’s Galena Ghost Tours offers bus rides around the city to experience some of the area’s spookiest spots through storytelling and the use of ghost hunting technology like EMF detectors. The Haunted Galena Tour Co. also offers a 90-minute walking tour of the city’s haunted locales. Or if you’re looking to combine your tricks with treats, the company also offers a Spirits and Spirits happy hour tour that includes alcoholic beverages as you learn about local lore. 

 

A ghost tour. Photo via Shutterstock.
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A ghost tour. Photo via Shutterstock.

Amelia’s Galena Ghost Tours

129 S Main St, Galena, IL, USA
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A ghost tour. Photo by Shutterstock.
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A ghost tour. Photo by Shutterstock.

The Haunted Galena Tour Co.

304 S Main St, Galena, IL, USA
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Sip Local

After all that walking, you’ll deserve a drink, and any visit to Galena is worth toasting to thanks to the community’s local producers. In addition to a number of local wineries, Galena is also home to a brewery as well as a well-known craft distillery. Located in the heart of downtown, the Galena Brewing Co. serves up beer flights and tasty menu options like a giant soft pretzel. Just outside of town along Historic Highway 20, Blaum Bros. Distilling Co. distills whiskey, bourbon, gin, vodka and more. In addition to a spacious tasting room, Blaum Bros. also offers distillery tours every day of the week.

 

The Galena Brewing Co. in Galena, Illinois.
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The Galena Brewing Co. in Galena, Illinois.

The Galena Brewing Co.

227 N Main St, Galena, IL, USA
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Blaum Bros. Distilling Co. in Galena, Illinois.
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Blaum Bros. Distilling Co. in Galena, Illinois.

Blaum Bros. Distilling Co.

9380 U.S. Highway 20 W., Galena, IL, USA
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Find a Festival

Don’t let its historic aesthetic fool you — Galena knows a party. There are tons of festivals and outdoor celebrations in this small town, especially during the fall. Embrace autumn with Galena’s annual Halloween Parade & Festival that draws thousands to downtown. In addition to a street party, the celebration includes a two-hour parade along Main Street with decorated floats, marching bands and the occasional pyrotechnics. The community hosts an annual Oktoberfest as well as Mallardfest, which includes wine for nearby wineries, a fish fry and more.

 

Downtown Galena, Illinois.
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Downtown of Galena, Illinois.

Downtown Galena

Downtown Galena, Galena, IL, USA
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