10 Fun Things To Do In Galena IL, USA

Last Updated on August 6, 2022

Galena is a small town that sits along Highway 20 in Illinois, USA.  It’s just under 3 hours from Chicago, making it perfect for a weekend getaway from the busy city! Galena has been named as one of the best small towns in America several different times. Here are 10 fun things to do in Galena IL!

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Things To Do In Galena IL

Where To Stay In Galena Illinois

You can find several different accommodation options for Galena Illinois on Booking.com. You can check different rates using the link below. There are several different chain hotels in Galena but if you are looking for something more unique, there’s: Chestnut Mountain Resort hotel, Cloran Mansion Bed & Breakfast, Irish Cottage Inn & Suites and Stoney Creek Inn to name a few!

In the early 1800’s Galena was a booming lead mining town with a population of almost 14,000.  Today it’s home to just over 3000.  Galena was once home to the former President, Ulysses S Grant, you can even take a tour of his old home!  Downtown features the ‘Helluva Half Mile’ shopping street, full of independent small businesses.  

I really like this area, it reminds me a lot of the high streets back home in the UK where you can pinball across the street and window shop without having to constantly get back in your car to visit different shops!  It also lays on the Galena River, where there are walking trails and places to relax!

Self Guided Downtown Galena Walking Tour

Galena’s Downtown is very walkable and photogenic!  There’s a small parking lot along the mainstreet with a crazy old fashioned (?) ticket machine.  I’ve never seen anything like it!  You fold up your dollar bills and then poke them through the slot which matches the number of the space you are parked in, with a little tool that’s attached to the machine! I’m not sure exactly how they can tell who’s paid, but hey I thought it was novel!

These photos could be followed as a circular walking route of Galena! Starting and finishing at the flood gates of the East end of Main Street.

Old Fashioned Billboard Advertisements

Something I love taking photos of now I’m living in America are all the worn out looking billboard advertisements, they really add to the character and history of the towns!

Galena Trolley Tours

The main guided trolley tour takes an hour and run year round.  There’s a stop right on Main Street so you can’t miss it if you want to take a tour of the Historic District!  Otherwise they are still fun to photograph!  The Galena Trolley Tours have been running since 1988, so have been in business for 30 years!

Old Fashioned Shop Front Signs

As mentioned above, Galena’s ‘Helluva Half Mile’ is jam packed with local small businesses and they all have these cool our fashioned signs!

Inside the Stores!

I LOVED wandering around the old fashioned pick n mix sweet shops in Galena!  When the sweets are displayed like this you can’t help but want to eat EVERYTHING in sight!  The Great American Popcorn Company had ‘Kitchen Sink’ flavoured popcorn, it looked disgustingly yummy (and I’m sure it doesn’t really come from the remnants stuck in a plug hole…). There are so many little independent businesses offering unique gifts and treats!

Helluva Half Mile North East end of Main Street

Galena IL Helluva Half Mile

This is one of my favourite photos from Galena!  I love the way the building looks and in the afternoons the sun always seems to be in the right place, just lighting up Main Street in the perfect way!

If you’re looking for somewhere to eat in Galena, I recommend the Log Cabin if you are feeling fancy or Gobbie’s Sports Pub and Eatery for something more casual (try the beer nuggets!).

At this end of Main Street you’ll also find the Dowling House, the oldest house in Galena and the oldest stone structure in Illinois.  The Dowling House was build in 1826.

The Galena River & Grant Park

Again, just look at the way the sun lights up the bridge!  This bridge crosses the Galena River near Main Street into Grant Park. In Grant Park, you’ll find a Little Free Library if you have any old paperback books that you feel like exchanging for something new!

Galena Train Station

The Galena Train Station building is a proposed station for a Dubuque, IA – Chicago, IL Amtrak Route (which NEEDS to happen), however the construction of this route has been put on hold, so for now, the station is unused.

You can either follow the river, cross back over the US20 bridge and you’ll be back at the flood gates, or continue away from Main St and head up towards the former President Ulysses S Grant’s house.  The house is open between Wednesday and Sunday for 25 minute tours.  There is a suggested donation of $5 for an adult.

The Old Cottage in the shadow of Ulysses S Grant’s House

This little old cottage is located just as you enter Galena (from Chicago direction, heading westbound towards Iowa).  There is a huge car park and steps leading up the hill towards Ulysses S Grant’s house (former US president).

Places to Visit Outside of Galena’s Downtown District

Chestnut Mountain Resort

🗺8700 W Chestnut Mountain Rd, Galena, IL 61036, United States

Chestnut Mountain is located 9 miles away from Downtown (but it is still part of the Galena area!)  In the winter it’s a ski resort, but in the summer it’s home to Segway tours, a zipline and an alpine toboggan slide that over looks the Mississippi River.  Pretty cool place for a ski resort if you ask me!

West Street Sculpture Park

🗺620 S W St, Galena, IL 61036, United States

The West Street Sculpture Park seems to be a bit of a hidden gem in Galena!  Despite living just 40 minutes from Galena and visiting several times, it took me a little while it discover that it existed! It was only when I was browsing Google Maps one day that I spotted it!

The Sculpture Park is free to visit and was created by John Martinson as a way to showcase his artwork.  You can pick up a map and wander around and view the sculptures at your leisure.  When I visited, there were 32 on display but I’d imagine that this may increase with more creations!

Blaum Bros Distilling Co.

🗺9380 US Hwy 20 W, Galena, IL 61036, United States

Blaum Bros is a working distillery that produces bourbon, vodka and gin. For $10 visitors can have a guided tour of the distillery (including tasting!). Tours run: Monday to Thursday at 3pm, Friday to Sunday at 1pm and 3pm (with an additional 11am tour on Saturdays). There’s also a cocktail bar which is open every day from 10am, which is very cozy and has table top games!

‘Eagle Ridge Resort & Spa’ and The Galena Territory

🗺444 Eagle Ridge Dr, Galena, IL 61036, United States

Unfortunately I never had the opportunity to visit Eagle Ridge Resort & Spa but I’ve heard lots of positive things about it! It sits on Lake Galena and has a golf course, indoor pool, spa and restaurant. Within the Galena Territory area you’ll find a Nordic Centre (for winter activities), a horse riding centre, hot air balloon rides and zip lining at Long Hollow Canopy Tours. They also hold several events throughout the year.

Galena Goat Yoga

🗺7306 US-20, Galena, IL 61036, United States

Another place that was on my bucket list was Galena Goat Yoga! I’ve done goat yoga a couple of times before and it’s always a fun experience! Classes last for 1hr 30 and include a 45 minute goat yoga session and an additional 45 minutes to play with the goats for $39.

Things To Do Near Galena IL


While you’re in the area, Dubuque is 15 minutes past Galena, just the other side of the Illinois/Iowa border.  It’s worth checking out while nearby, you may find this post useful for things to do in Dubuque if you decide to visit! It lies along the banks of the Mississippi River and has many places to eat and fun attractions such as the Fenelon Place Elevator and the National Mississippi River Museum Aquarium. During the winter Sundown Mountain Resort is open for skiing, or during the summer, the Mines of Spain is a great area for hiking.

Highway 20

Galena sits on Highway 20, the longest highway in the USA. Here are a couple of guides you may find useful if you are travelling either east or west bound along the route!.

(Galena IL to Waterloo IA) America’s Longest Highway: Awesome Events & Roadside Attractions Along Highway 20 in East Iowa!

(Chicago IL to Galena IL) Chicago To Galena Road Trip: Must See Stops in Illinois USA

I hope this post has inspired you and given you some ideas of things to do in Galena IL! Any questions, let me know!

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5 thoughts on “10 Fun Things To Do In Galena IL, USA

      1. I love Galena. I had to book a carpet cleaning in La Grange for my daughter, so she came to visit me and we took her son on a trolley ride. It was so fun! Thanks for including that!

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