The Mississippi River Town That Survived Economic Collapse to Become a Charming Tourist Haven

Galena, Illinois

Galena is what would happen if you froze a charming river town in its 1850s prime, then added great restaurants and modern B&Bs.

Main Street’s lined with red brick buildings that once hosted Lincoln, while new wine tasting rooms and art galleries keep things from feeling like a museum. Here are some of our favorite things to do in Galena, Illinois.

Hike with friendly goats

At Hoof It Goat Treks, you can walk 1.25 miles through land that’s been in the same family for four generations. The hike takes 45-60 minutes and is open to all ages. There are 29 friendly goats who follow you through the woods and prairies.

If you want something extra special, try their wine tours or evening bonfires with live music at their farm on Devils Ladder Road. The goats love the attention and will happily let you feed them treats along the way.

Hunt for Galena’s ghosts

Ghost hunters love Galena because its valley shape keeps spiritual energy from escaping. The first ghost sighting was recorded back in 1845 when folks reported seeing the spirit of a War of 1812 veteran.

You can join tours from three different ghost tour companies all year long. People often see strange things at Turner Hall, DeSoto House Hotel, and Galena Cellars Winery. Both visitors and staff have spotted ghosts and experienced weird events they can’t explain in these old buildings.

Go on a spirits-tasting tour

Matt and Mike Blaum started their distillery in 2013, and now over 125,000 people visit each year. They use a special copper still to make bourbon, rye whiskey, vodka, gin, and Hellfyre (a spicy vodka with three kinds of peppers).

You can take daily tours that end with taste tests. The brothers control everything from grinding grain from Jo Daviess County to bottling at their location on US Highway 20. Their handcrafted spirits have won awards and attracted visitors from across the country.

Explore the Galena’s historic Main Street

You’ll find over 125 unique shops in old buildings that haven’t changed much since the 1850s. The historic district covers 581 acres and is on the National Register of Historic Places.

You can shop at art galleries, antique stores, and specialty food shops in buildings that look just like they did during the town’s boom years.

Don’t miss local favorites like Galena River Goods, Galena Book and Paper, and the Galena Spoon Company, where you can watch craftspeople making wooden kitchen tools right in their downtown workshop.

Try sleeping in a former county jail

The old Jo Daviess County Jail has been turned into the fancy Jail Hill Inn. You can still see original features like two-foot-thick walls, cement floors, brick arches, and prisoner carvings in Suite 301.

This four-story brick building from the 1800s now has six luxury suites with steam showers, whirlpool tubs, and sound systems. If you stay in Suite 202, which was once where the sheriff’s family lived, you’ll enjoy 9-foot-tall windows with great views of downtown and the Galena River.

Try goat yoga

At Galena Goat Yoga, you can do downward dog while actual baby goats play around you. The Montgomery family started this fun activity in 2018 on their renovated farm. Classes run for 60 minutes and are good for all skill levels.

They keep classes small with no more than 25 people so everyone gets personal attention. The playful baby goats like to jump on your back during poses, making everyone laugh.

After class, you can take photos with the goats at their farm just 10 minutes from downtown.

Stroll on an ancient mound

At Casper Bluff Land and Water Reserve, you can walk on a rare Thunderbird-shaped mound that spans 112 feet. Native peoples built this sacred site about 1,000 years ago during the Late Woodland period.

The 325-acre conservation area has 51 ancient burial mounds alongside restored prairie land. From the limestone bluffs, you can see amazing views of the Mississippi River.

During migration seasons, you might spot some of the 140 bird species that visit here. The site opened to visitors in 2008 after archaeologists studied it thoroughly.

Explore an abandoned rail tunnel

The Winston Tunnel, built in 1888, runs 2,493 feet through unstable shale rock. It took 350 workers nine months to build and cost $600,000 (about $18 million in today’s money). The tunnel was nothing but trouble, needing constant repairs and a huge fan powered by a 310-horsepower diesel motor to provide air.

The Chicago Great Western Railway gave up and abandoned it in 1971. Now the western entrance is part of a 230-acre state natural area. Many locals believe the tunnel is haunted, especially since at least one worker died during construction.

The oldest hotel in Illinois has welcomed guests since 1855

DeSoto House Hotel opened in 1855 and hasn’t stopped operating since, making it the oldest hotel in Illinois. This impressive five-story brick building cost $85,000 to build (about $2.7 million today).

Now it features 55 rooms with Victorian-style decor and has hosted famous people like Abraham Lincoln and Stephen Douglas. When it first opened, it had 225 rooms, but after a fire in 1880 and renovations in the 1980s, the hotel was reconfigured.

Now it also houses restaurants and shops alongside guest rooms in downtown Galena.