5 Galena Day Trips from Chicago Worth the Money

1.Downtown Galena Food and Drink Tour

★★★★★★★★★★5.0 · 52 reviews · 2 hours 30 minutes (approx.) · from $86Our pick

Walk historic downtown Galena with a guide such as Devin, stopping at five food and drink venues for up to nine tastings. Try an empanada, specialty soda, cheese-shop fare, and, depending on the tour time, Mediterranean dishes or local beer. The 2.5-hour outing costs $86 per person, and restaurant staff gratuities are included.

“Devin was a very knowledgeable tour guide. He knew the people at each restaurant and our tastings were ready quickly. He was very personable, we enjoyed our time with him on the tour.”

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2.Groovy Galena Scavenger Hunt

★★★★★★★★★★3.0 · 15 reviews · 2 hours (approx.)

Start at Galena Roasters and follow a digital scavenger hunt through Galena, with a live remote host sending clues and reacting to your photos and videos. Expect a mix of indoor and outdoor checkpoints, local history, a mural challenge, and stops such as Galena Cellars Vineyard and the Galena and U.S. Grant History Museum. Bring a charged, data-ready phone.

“So much laughter, so much fun! We had a great time and recommend this for any group! Learned about Galena, and had fun while doing it.”

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3.Zipline Adventure- Long Hollow Canopy Tours

★★★★★★★★★★4.7 · 8 reviews · 2h 30m · from $109

At Long Hollow Canopy Tours near Galena, two English-speaking guides lead a small group of up to eight on a 150-minute course with six increasingly long ziplines, a wooded UTV ride, a 140-foot skybridge, and a 40-foot descent by rappel or optional free fall. You need closed-toe shoes and must meet the weight and health requirements.

“Our family totally enjoyed our experience at the zip line. 3 of us were totally inexperienced. The team did a great job of training and encouraging us. When we needed help, they were right there to assist and did everything possible to make the experience fun and memorable.”

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4.Zipline Adventure in Galena, Illinois

★★★★★★★★★★5.0 · 5 reviews · 2 hours 30 minutes (approx.) · from $103

Long Hollow Canopy Tours’ 2 to 2.5-hour outing pairs an off-road UTV ride with six ziplines, a 40-foot rappel and a 140-foot suspended sky bridge. The final zipline runs 1,250 feet. Guides teach Ground School, then coach you through the course. At the last platform, choose a free-fall jump or a rappel.

“Absolutely fabulous! Great experience and terrific instructors. They need to get a raise, a very big one.”

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5.Aerial Adventure Park- Long Hollow Canopy Tours

★★★★★★★★★★4.7 · 4 reviews · 2 hours · from $69Best value

Spend two hours at Long Hollow Canopy Tours in Galena, with 30 minutes for harness fitting and Ground School before 90 minutes on a treetop course. Choose from 40 challenges, explore two treehouses and finish on side-by-side 400-foot ziplines. Guides Aiden and Caden have been praised for their clear, friendly help, though the obstacles can be a serious workout.

“Super well organized and the staff is lovely and so fun! We felt safe and picked up the safety harness system with ease. Aiden and Caden were our tour guides and they were great. My only critique is that I did not fully understand what I was signing up for. This is a difficult two hours with lots of challenging elements. The easy course is not that easy and the difficult elements are REALLY tough. Get ready for a two-hour workout!”

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