From Our Blog

The Best of the Best in Galena

Traveling from Chicago to Galena? Here are 11 Things to Do on the Way!

Road Trip from Chicago to Galena This FallWe love a good road trip. Are you ready to make the road trip from Chicago to Galena? We have the perfect guide for you!

Summers in Galena are filled with plenty of fun and adventure, and this summer has been no exception. There’s still plenty of time to get here and enjoy the best of Galena with us this summer, whether it’s biking down the Galena River Trail, kayaking on the river itself, shopping along Galena’s Main Street, or relaxing and enjoying the warm weather on our private patio.  But really, now is the perfect time to plan your fall getaway to the beautiful, rural town of Galena. Galena is only a one-tank road trip from Chicago, and there’s plenty to see and do as you make your way from Chicago to Galena.  Getting here is half the fun. Get started on your adventure, and book a room at our luxury Bed and Breakfast in Galena today.

11 Things to See From Chicago to Galena

Galena is the perfect romantic getaway destination for anyone living in Chicago. It takes just about 3 hours to get from Chicago to Galena. Not only is the destination worth it, but the journey is rewarding and beautiful as well.  The most common route to travel from Chicago to Galena is Highway 20, which itself actually happens to be the longest stretch of highway in America.  The first of the towns you’ll come to as you near Galena is Road Trip from Chicago to Galena This FallStockton. Here, you’ll want to take a look at their murals, and maybe even strike a pose in front of them; these murals are regulars on Instagram.

As you head out of town, stop by the Woodbine Bend Golf Course and Restaurant. They have a wonderful links-style golf course, and a delicious restaurant on-site with a great selection of craft beer; perfect for lunch before you continue on your way.

Continue on your journey from Chicago to Galena, and you’ll next find the charming town of Elizabeth, Illinois. Terrapin Orchards is a great place to stop in, especially if you want to take a small piece of Galena home with you. In the earlier summer months, they have u-pick strawberries available. But as we get closer to fall, apple season comes into view.  Some varieties begin to ripen in mid-August, but most make their debut in September and October when things at the apple orchards are in full swing.

Dittmar Farms is another wonderful, locally-owned farm that is worth the stop as you come through Elizabeth. Afterward, you can learn more about the history of the area at the Chicago Great Western Railway Depot Museum, followed by a refreshing ice cream cone at Three Sisters Sweet Shoppe. Other delightful businesses to visit in Elizabeth include E-Town Coffee shop, Common Cents Resale Shop, and Elizabeth Grand Antique Mall.

Arriving in Galena on Highway 20

Once you’re back on highway 20, take a moment to appreciate the views on either side of the road. The gently rolling hills dotted with small farms and cows and the densely wooded areas make for a truly beautiful drive, especially during the colorful fall months. The Long Hollow Scenic Overlook is a great place to stop and take in the views.

From there, continue down Highway 20, and the historic streets of Galena will soon come into view. Galena’s charming downtown is filled with historic buildings, each appearing as though they’re frozen in time. Galena was once a thriving mining and river port town. Today, it’s restored 19th-century buildings offering visitors something new; a chance to step back in time and take things moment by moment. These Road Trip from Chicago to Galena This Fallbuildings house a delightful array of art galleries, independently-owned boutiques, and delicious restaurants. At the end of Main Street tucked up on a hill, you’ll find our luxury Bed and Breakfast; the perfect place to end your road trip from Chicago.

Hopefully, you take your time over the coming days while you’re in Galena to thoroughly explore this quaint town, and appreciate its immense charms.  But if you want to continue exploring the area, all you need to do is get back on Highway 20 and head further west. It will take you straight to the mighty Mississippi River. Make a stop at Gramercy Park in East Dubuque, and enjoy the breathtaking views overlooking the river. The park is also a natural heritage landmark, home to 26 ceremonial and burial mounds. It’s a great place to watch a sunset over the river. You can also enjoy waterfront dining in East Dubuque, at Millennium Bar & Marina.

Soon enough, you’ll see why we see guests come back to Galena, and the Jail Hill Inn, time after time. There’s something special about this charming town that you really must see for yourself. Treat yourself to the perfect getaway, and road trip your way from Chicago to Galena this fall.  To get started, book a room at the #1 ranked Bed and Breakfast on TripAdvisor, Jail Hill Inn!

Scroll to Top

Give The Gift of Jail Hill Inn This Christmas

Give your loved one a very special gift of a stay at Jail Hill Inn .  We offer gift certificates in many amounts.