Here are the best Things to Do in Galena, Il

Start your day with a sumptuous 3-course gourmet breakfast at Jail Hill Inn, the most luxurious Galena Bed and Breakfast. From there, head to downtown Galena’s Historic Main Street just 1 block away. As you head south on Main Street, take in the scope of Galena’s extraordinary range of shops, historic architecture, and friendly small-town charm. Exploring Galena’s Main Street is one of our favorite things to do in Galena, IL, as it is filled with over 100 different shops and boutiques.  

Some of our guests’ favorite stores to visit include The Towne Rebel, The Galena Canning Company, Galena Candle and Bath, Vignettes, Simply Elegant, Elle & Becks, Isabella’s, Poopsies, River Bend Gallery, and Images of Nature Gallery.

At some point, while browsing shops, you’ll be ready for a small bite to eat. Stop in for a light lunch and great coffee at Big Bill’s Café. After lunch, take a trolley tour. This one-hour tour is a great way to learn all about the historic significance of Galena, as well as see many of the most important sites in town. When you’re done, grab a cocktail or glass of wine at Galena River Wine & Cheese, Jamie’s Wine Studio, or the Green Street Tavern.

Be sure to also enjoy Jail Hill’s Wine and Appetizer trays, which are delivered to your room to be enjoyed at your convenience every afternoon. It’s the perfect way to unwind after a day of shopping and sightseeing. Cap off your evening with a delicious dinner at one of our favorite local Galena restaurants, Fried Green Tomatoes.

When you’re ready to leave the Inn for the day, head down the street and cross the Meeker Street Footbridge. It will take you directly to the Galena River Trail, where you can enjoy an easy, beautiful day hiking or biking.

It’s a great way to work off your breakfast and is one of our favorite things to do in Galena, Illinois! The Galena River Trail follows the meandering Galena River and extends for over 10 miles from downtown. Along the way, the trail passes Galena’s historic Grant Park, the Train Depot, and plenty of beautiful wooded areas, farmlands, and bluffs. For an interesting side trip from the Galena River Trail, walk up Bouthillier Street and tour president U.S. Grant’s home, which is now owned by the State of Illinois.

After a day of hiking and exploring, come back to the Inn to relax on our third-floor back deck or main-level patio. You can even schedule an in-room massage by one of our approved massage therapists; the perfect antidote to those tired muscles!  

After you’ve enjoyed a little bit of downtime, head to the Blaum Brother’s Distillery for their 3 pm distillery tour. Here, you’ll learn about their craft bourbon, vodka, gin, and whiskey, each made with ingredients sourced from this region. After the tour, come back to the Inn to enjoy our daily wine and appetizer trays, before heading out for a romantic dinner at Fritz & Frites, our innkeepers favorite restaurant in Galena. 

Fuel up for your day with Jail Hill Inn’s incredible 3-course breakfast; you’re going to need it! Next, head to our local outfitter in Downtown Galena. Here, you have the choice between renting bicycles, canoes or kayaks, and even stand-up paddleboards.

From there, you’re free to spend the morning enjoying a leisurely bike ride or paddle. If you’re here during the winter, this is the perfect day to check out Chestnut Mountain Resort. You can rent skis or snowboards, and enjoy picturesque views of the Mississippi River the entire time you’re hitting the slopes. If it’s your first time skiing, they also offer ski lessons from their highly trained instructors.

After your adventurous morning, grab a late lunch downtown at Durty Gurts. From there, work your way back to the Inn, stopping along the way at our Old Blacksmith Shop. It is an authentic 1897 blacksmith shop, complete with working forges and filled with tools and equipment over its 100-year history. Tours are available if you’re interested.

Once you’re back at the Inn, enjoy our daily wine and cheese appetizer trays, and relax for the remainder of the evening, stepping out only for dinner at Log Cabin Steakhouse.

Though there are more than enough things to do in Galena, IL, there’s a fantastic assortment of activities in the countryside, too. After filling up at our Galena Bed and Breakfast, hop in your car and head out to explore some of the small towns in the surrounding countryside.  Ten miles east of Galena is Elizabeth, IL. Elizabeth is a great town for the antique lover, and is home to two popular antique stores: Common Cents and the Elizabeth Grand Antique Store. Visit historic sites in Elizabeth, The Blackhawk Fort is home to excellent exhibits worth checking out.

Grab a late lunch and a fantastic cup of coffee at E-Town Cafe in Elizabeth before heading north for more adventure.

Your next stop will be in Schapville, IL. Here, check out “A Bushel and a Peck” country store, which houses a great collection of antique, vintage, reclaimed, and re-purposed home furnishing and decor. From there, continue on to the quaint town of Scales Mound, IL. Ninety percent of the town is on the National Register of Historic Places.

If you need a nature break, enjoy some great hiking northeast of here near the Wisconsin border, at the Apple River Canyon State Park. This area is captivating, with its limestone bluffs, deep ravines, springs, streams, and wildlife.

You’ve seen so much during your time in Galena. Come back to the Inn one final time, and enjoy relaxing with your customized afternoon wine and appetizer tray. This is a great night to grab some takeout or order in at the Inn! Cannovas Pizza and Procentos Pizzeria are both great options.