Horseshoe Mound Scenic ViewImage: Horseshoe Mound Preserve

Follow roads less traveled through the captivating Driftless Area. Enjoy the nuances and showstoppers during a leisurely drive where natural and man-made worlds meet. What you’ll encounter—mile after mile—is geologically and aesthetically special.

Welcome to the Driftless Area—20,000 square miles in four Midwestern states that Ice Age glaciers bypassed many thousands of years ago. The slow slithering of ice (at least one mile thick) bulldozed much of the Upper Midwest, changing the landscape forever. But not here. See the unspoiled beauty by cruising for the joy of it or with a specific destination in mind. Consider the following trio of options.

17 miles between Galena and East Dubuque

Highway 20, a 3,365-mile, east-west thoroughfare, links Boston, Massachusetts, with Newport, Oregon. The small but lovely stretch heading northwest from Galena is a mix of woodsy thickets, gently rolling hills and farmland. Play 18 at Galena Golf Club, which has been open since 1927 and was redesigned in 2003. Check out bounty and display plots at Murphy’s Gardens, where the farmers-market vibe grows with the ripening of crops.

Hungry? You’ll have to exit Highway 20, but Mulgrew's Tavern's world-famous foot-long chili dog is worth the extra miles. Or climb a bluff top for Sunday brunch, a steak dinner or cocktails at Timmerman’s Supper Club, known for expansive Mississippi River views. 

Stretch your legs with a game of foot golf—played with a soccer ball—at Lacoma Golf Club, where there are 45 holes for the traditional game as well. Thumser’s 19th Hole, a short jog up Highway 35, both entertains the family (with a mini-golf course) and fills them (with burgers, broasted chicken and pizza).

16 miles, between Galena and Hanover

Look for an entrance sign to Horseshoe Mound Preserve and drive a long gravel road uphill. Mowed paths lead hikers through the 40-acre property, and on a clear day, you’ll enjoy views of three states. The panoramic vistas alone are worth the visit, but then there are interpretive displays, a monarch-friendly butterfly habitat, a fairy door at the base of a tree to entice the kids, and a “council ring,” where chunky slabs align with solstice sunsets.

A little farther south, the eight-mile, crushed-rock Galena River Trail connects to a hiking-biking trail for overnight guests at LeFevre Inn & Resort, full of countryside charm. Find Goldmoor Inn for a gourmet dinner for two. Enjoy a stroll along the trackbed of a retired railroad route at Winston Tunnel State Natural Area. Although the 1888 Winston Tunnel closed long ago, it is still a fascinating site in breathtaking surroundings.

Nearby, Chestnut Mountain Resort offers more adventurous outdoor activities - mountain biking, ziplines, skiing, and more to engage all ages. Venture from Blackjack Road for a few quick side trips, including Iris and Jack Witkowsky State Wildlife Area (ideal for hunters) and Blanding Landing (for fishing, birding, picnics, camping and silent sports-canoeing to hiking).

27 miles, between Galena and Warren

Turn the clock back to the mid-1800s and imagine what it was like to see this part of Illinois from a horse-drawn carriage en route to Chicago. Cross the Galena River and notice the cattail marshes, hilltops, ravines and farmland. Stop for a wine tasting and patio view at Galena Cellars Vineyard & Winery.

Get acquainted with Scales Mound: The entire village—a historic district in the National Register of Historic Places—sits at the highest point in the state at 1,235 feet and is said to be "At the Top of Illinois." Sprinkled throughout the drive are colorful quilt squares painted on the sides of barns. The private Oak Hill Farm, 170 acres and around since 1875, retains down-to-earth charm while hosting elegant weddings. Wedding celebrants enjoy the property’s one-room schoolhouse, charming chapel, renovated bar and outdoor spaces, including woodlands, a pond and the Apple River.

The river might appear peaceful, but Apple River Canyon State Park tells a bigger story. Until 1892, the site of the frontier town of Millville was flooded, destroying it. Today, the area is known for trout fishing, nature trails, and dozens of campsites.

Nearby, Warren hosts the oldest county fair in Illinois in late July and the popular Warren Pumpkin Festival in September, which includes pony rides and tractor pulls.

There's no end to the beauty of Galena Country. If you have more time to explore, consider these additional scenic drives:

14 miles, between Scales Mound and Elizabeth

Notice the contrasts, like weathered farms and shiny solar panels. Shop two floors of antiques and local goods at A Bushel & A Peck. Book a guided trail ride at Shenandoah Riding Center, which is a short drive from the main road. Tour a reconstructed fort at Apple River Fort State Historic Site. Time your visit for one of the fort’s special events to experience living history demonstrations.

10 miles, between Galena and Council Hill

Find laid-back Council Hill Station—the only business that remains from an 1854 European community—for acoustic music, a large beer selection, historic buildings and ruins frozen in time. Also nearby and delightfully rural: the 1894 Little White Church on the Hill. Expect a pretty mix of modest farms, rural estates and neatly tilled cropland between this area and Galena.

9 miles, between Galena’s southern outskirts and Rodden Road

This roadway dips, twists and veers through canopies of shade, then multicolor splashes from gardens. Lush farmland shows so many shades of green. The most romantic surprise: Inn at Irish Hollow, providing luxurious overnights in a suite or cottage on 500 acres with pristine pastures, woods and glacial streams.

Ready to embark on your outdoor adventure through Galena Country's picturesque landscape? Galena and its surrounding countryside offer something for everyone! So grab your official visitor's guidebook your stay, and get ready to explore the natural beauty of Galena Country. Your adventure begins now!