Road Trips Through Illinois' Small Towns

A road trip through small towns and along river roads is the best way to see not only beautiful scenery, but the heart and soul of Illinois.

by Jamie Bartosch in Regional Getaways, Road Trips
September 20, 2018

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Route 66 may be the state’s most famous road, but it’s by no means the only drive worth taking. Whether you’re in a two-seater convertible with the top down or in a minivan full of kids, see Illinois from the car window—especially when the fall colors light up the foliage with bright colors—get in the slow lane, make frequent stops and enjoy the scenic cruise.

Sheridan Road, from Evanston to Lake Forest

It’s fun to gawk at the gorgeous, multi-million-dollar estates—including several privately-owned Frank Lloyd Wright-designed homes—along Sheridan Road. The twisty road winds through Illinois’ wealthiest suburbs (an area known as the North Shore) and along Lake Michigan. It’s a roughly 30-mile stretch from Evanston to near the Wisconsin border. Pass leafy ravines, the stately campuses of Northwestern University and Lake Forest College, and the architecturally stunning Baha’i Temple that towers over the road in Wilmette.

Old movie fans might recognize some of the scenery from the many movies filmed in this area, including Risky Business, Ferris Bueller’s Day Off, and Home Alone. Stop for a picnic and concert at Ravinia, the legendary outdoor music venue, or stroll through colorful flowers and plants at Chicago Botanic Garden. Spend the night at Lake Forest’s historic and newly renovated Tudor mansion, Deer Path Inn, famous for its English breakfast.

Illinois' Southern Hills

Oak, maple and ash trees show off beautiful ruby and yellow colors along State-127 from Murphysboro to Jonesboro in southern Illinois. The road covers less than 25 miles, but it can take all day to explore if you stop at local wineries and fruit orchards near Shawnee National Forest. Halfway through the drive, in Alto Pass, pull into Root Beer Saloon, a kitschy, taxidermy-filled cafe that serves Cajun food and a variety of drinks in frosty mugs, including microbrew root beer from a keg.

Great River Road, from Hartford to Grafton

Start this scenic drive at the Lewis and Clark State Historic Site in Hartford, and then, just like the explorers did, follow the Illinois and Mississippi rivers as they converge with the Missouri, just north of St. Louis. Busy bird sanctuaries, tall limestone bluffs, old river towns, scenic overlooks, wildlife refuges, Pere Marquette State Park and a river museum dot this 33-mile route. To really feel like an explorer, paddle down a small stretch of the Mississippi in a replica trader canoe from the Alton Marina.

Northwest Illinois Loop

One of Illinois’ prettiest drives is in and around Galena. Bald eagles soar overhead as you cruise along a loop of relaxing, rolling hills from Galena to Freeport, Oregon and Savanna. The route goes past 19^th century buildings, the world’s largest mallard duck hatchery in Hanover, and the thick groves in White Pines Forest. Pull over at Mississippi Palisades State Park, where there are Instagram-worthy river views, plus outdoor recreation like hiking and fishing. In Oregon, Lowden State Park is home to the 48-foot-tall Eternal Indian statue (aka The Black Hawk), perched on a bluff overlooking the Rock River. An ice cream stop at the old-fashioned Union Dairy in Freeport will put you next to the town square where the second Lincoln-Douglas debate was held.

Lincoln Highway

Thirty-five giant, interpretive murals are painted on walls along this 179-mile drive, which runs along U.S. 30, and Illinois 31 and 38. Each mural tells a fascinating but true story about the town and the road, like when the new trolley line came to New Lenox, or when the trendy “auto camping” ground opened in Joliet in the 1920s. Pretty gazebos line the way, too.

This is the only home Wright designed specifically for a person with a disability

Illinois' Frank Lloyd Wright Trail

Thirteen of the famous architect’s Prairie-style buildings are located along this self-guided drive that stretches from Springfield to Rockford. There’s some city driving involved as some of the stops are in Chicago. But even if you don’t want to venture into city traffic, there are plenty of other stops, including Bradley House in Kankakee, where visitors admire Frank Lloyd Wright-inspired murals downtown.

Illinois River Road, from Havana to Ottawa

This one-way route starts in Havana and heads north along the river to Chautauqua National Wildlife Refuge. There, more than 250,000 waterfowl, including bald eagles, feed and rest during their annual spring and fall migrations. An easy trail leads to observation platforms along the lake. Head north along the river to Peoria, where you can connect with Grand View Drive, a 2-mile stretch which President Theodore Roosevelt called “the world’s most beautiful drive.” It threads through neighborhoods to a tree-lined road that peaks at an enclave of mansions along a bluff-top park, with views of the river.

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Road Trips Through Illinois' Small Towns

Sheridan Road, from Evanston to Lake Forest

Illinois' Southern Hills

Great River Road, from Hartford to Grafton

Northwest Illinois Loop

Lincoln Highway

Illinois' Frank Lloyd Wright Trail

Read more about Illinois' Frank Lloyd Wright Trail