West on I-90 to Route 20 for a great fall getaway

By Maureen Callahan

Thinking of heading out for a weekend this fall? Most Chicagoans leaf-peep in Michigan or Wisconsin. This year, take I-90 west to Route 20 west for some fun fall destinations.

Rockford

Head of the Rock Regatta
Photo courtesy of GoRockford

Originally named Midway, due to its situation halfway between Chicago and Galena, it became Rockford due to the Rock River’s rocky ford, which bubbled near the first settlement. Art lovers, take a detour to the Rockford Art Museum, which holds the most significant collection of Chicago art anywhere inside – or outside – the city.

The Rockmen Guardians by artist Terese Agnew
Photo courtesy of GoRockford

Each fall, the second week of October sees the Midwest’s best collegiate rowing teams face off at Head of the Rock Regatta. Many of these crews use the race as practice for the Head of the Charles Regatta – the country’s oldest collegiate sporting event in Boston – the following weekend. Cheer on these highly skilled athletes as they race against the clock in this unique sport.

While you’re there, snap a photo with the Rockmen Guardians, found along the Rock River recreation path. You can’t miss these unusual 12-foot sculptures, made of granite boulders.

Galena, IL

Galena’s historic shopping district
Photo courtesy of Galena County Tourism

Before you get to town, stop at Chestnut Mountain for 2,000 feet of fun on the resort’s Alpine slide! Control your own pace as you ride downhill through 2,000 feet of scenic twists and turns with views of the Mississippi River.

Galena – a gem of a historic setting on the state’s eastern border – seems like something out of a movie. It has, in fact, made several silver screen appearances.

There’s something for every taste here. History hackers won’t want to miss the home of Ulysses S. Grant, given to the Civil War General upon his return home from the war. The nearby Belvedere Mansion, also open to tourists, is just a short walk down the street. If you need one more historic site, check out the Dowling House. The limestone structure was the town’s original trading post.

Get outside on a trolley tour, a boat tour on the Galena River, or get a bird’s eye view from a hot air balloon. Find the perfect memento in one of the many art galleries, antique shops, and eclectic boutiques.

Dubuque, IA

Dubuque’s Fenlon Place ascends to amazing lookout points.
Photo courtesy of Travel Dubuque

Welcome to the place where Iowa began. It’s full of scenic overlooks on the Mississippi River that come alive under fall colors. Impressive turn-of-the-20th-century mansions – many of which have become guest houses – dot rugged limestone bluffs. To get a better view, take the world’s shortest and steepest funicular railway, the Fenelon Place elevator, 189 feet up a sharp incline to an all-encompassing view of the river. Be sure to leave time to shop for antiques, spices, and other curiosities in Dubuque’s adorable downtown area.

Another half hour past Dubuque is Dyersville – filming location for the 80s baseball flick Field of Dreams. You can visit the movie set, play a few innings on the field, and have a pint in the onsite Dugout Pub.

Before long, you’ll be asking yourself, “Is this Heaven?”
No, it’s Iowa!