Fun Things To Do In Galena, Illinois USA

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!

Things To Do In Galena IL

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

Galena IL Advertisement Billboard

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

Galena IL 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

Galena IL Small Business Helluva Half Mile

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!

Galena IL Helluva Half Mile

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…)

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!

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

Galena River IL

Again, just look at the way the sun lights up the bridge!  This bridge crosses the Galena River near Main Street into Grant Park.

Grant Park

Galena IL Grant Park

Galena Train Station

Galena IL 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

Galena IL

This little old cottage is now 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

Galena IL Chestnut Mountain Resort

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

West Street Sculpture Park Galena

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!

Visiting Galena IL

I really need to stop and take a picture of The Irish Cottage Boutique Hotel along HWY20.  It’s an Ireland themed hotel, spa and pub but from the outside, the building is designed to look like lots of little shop fronts!  I drive by it all the time on the way to Chicago!

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!

My Galena Bucket List

Original Goat Yoga

Eagle Ridge Resort & Spa

You can find more about visiting Galena at

Follow Visit Galena on Instagram @visitgalenaorg

Follow me (Between England and Iowa!) on Instagram @englandandiowa

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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Things to do in Galena IL
Things to do in Galena Illinois USA
Things to do in Galena Illinois USA

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