20 Stops on Historic Route 20

Get your kicks on … Route 20? You bet. From its start in New York to its terminus in Oregon, this rambling road takes travelers on a true cross-slice of American history and culture.

Get your kicks on … Route 20? You bet.

Route 66 is lodged in the nation’s consciousness after a decades-old TV show and catchy hit song immortalized the highway. But rumbling, rustic U.S. Route 20 actually is the nation’s longest road. Stretching 3,365 miles from Boston to Newport, Ore., it rivals Route 66 in conjuring the romance of the open road.

The 145 miles of this road that cross our region from suburban Chicago to Dubuque are particularly scenic and emblematic of America, packed with places worth seeing.

“Route 66 is associated with the great American road trip. Route 20 is seen as a local highway,” says Bryan Farr, founder of the Massachusetts-based Historic U.S. Route 20 Association. His group exists to change that misconception, most prominently through historic roadside signage, to get travelers as excited about Route 20 as Route 66.

Around Galena, the highway closely follows the path of a pioneer road once plied by lumbering ox carts carrying lead from the local mines to the port of Chicago. Route 20 in northern Illinois reveals America, what formed it and what emerged from the strivings of pioneers and the generations that followed.

“Route 20 offers a view of our westward expansion. You can see the country unfold – its culture, architecture and history,” says Farr.

This is by no means flyover country. This is stopover territory. Route 20 is a retreat to an idiosyncratic back road, a respite from the monotony of the interstate and a panorama of people and places often taken for granted but essential to American identity. “Some of what you can see is forgotten culture,” says Farr. “But this is what made us. This was important.”

A road that runs through our backyard is a portal to everywhere. This fun and eye-opening trip transports a traveler far beyond the region’s surface-level familiarity.

Elgin History Museum
The Elgin National Watch Co. was once the nation’s leading watch manufacturer. From 1867 to 1965, it produced more than 60 million watches and buttressed the robust manufacturing base in the city of Elgin.

The company’s history and work are memorialized at the local history museum, where one of seven permanent exhibits includes displays of pocket watches, wristwatches and timing devices made for aircraft and ships in World War II. More exotic watches include a salesman’s watch with a crystal backing for a salesman to use in demonstrations, a doctor’s watch with a large-sweep second hand to take a pulse, and painted dial watches, all the rage in the late 1800s.

Also here are original watchmaking tools from the factory and a wall mural of the clock that once graced the factory’s immense tower. But the collection’s crown jewel is the 13th watch produced on the famed assembly line.

Big Thunder Memorial, Belvidere
Heading west from the suburbs, drivers will find a rough, reddish granite boulder near the Boone County Courthouse, located a few blocks off Business Rt. 20. This boulder was placed here in 1924 by the local Daughters of the American Revolution. Big Thunder, a Potawatomi chief, died before settlers came in droves in the 1830s. Following an ancient custom, his tribe buried him above ground, clothing him in his best ceremonial garb and sitting him upright inside a 6-foot-high stockade. They left him with pipes, tobacco and food for his afterlife journey. Souvenir hunters passing through on stagecoach pilfered the items and at some point even filched his skull and bones.

Sock Monkey Statues at Midway Village Museum, Rockford
Not sure what a sock monkey is? Visit Rockford and you’ll become an expert on them in the amount of time it takes to put on a pair of stockings. Sock monkeys date from 1932 during the Great Depression, when the only toy many families could afford was, well, a stuffed old sock. That year the Nelson Knitting Co. in Rockford launched the Red Heel Sock. Crafters found the colored heel was perfect for a monkey’s goofy gaping mouth, and thus the world was gifted with the kitschy monkey-like stuffed toy.

Midway Village Museum, located a mile or so north of Business Rt. 20 in east Rockford, has the patent for the signature sock and a perfectly silly 7-foot simian named Nelson, the world’s largest sock monkey. More than a dozen fiberglass sock monkey statues can be found at the museum and around town. They may appear poised to engage in monkey business, but they also dress appropriately. A monkey at Rockford University wears the school’s purple color while the Rockford Speedway monkey wields a checkered flag, and the little ape at the airport lugs a suitcase. Continue west on Rt. 20 and you may also spy the remnants of the factory where it all began.

Memories of the Rockford Peaches
Peachy keen is an apt description of the resurgent status of Rockford’s women’s baseball team, thanks to a new Amazon Prime series. The Rockford Peaches, of course, were part of a World War II-era women’s professional baseball league that was immortalized in the 1992 film “A League of Their Own” with its all-star cast of Tom Hanks, Geena Davis, Madonna and Rosie O’Donnell. The Peaches’ actual home field, Beyer Stadium, was torn down in the 1990s but has been somewhat reconstructed. You can play catch on the historic field or watch the occasional baseball game.

A special Peaches fan trail in Rockford includes a colorful mural at Seventh Street and Sixth Avenue, the “Girls of Summer” exhibit at Midway Village Museum and a Peach Wheat beer at the Prairie Street Brewing Co. downtown.

Yep, there’s no crying in the state’s fifth-largest city with the enduring popularity of the Peaches.

Little Cubs Field, Freeport
This charming oddity lends credence to the theory that the Chicago Cubs draw legions of fans especially because of the quaint charms of their ballpark. This Wrigley Field replica, lovingly built by volunteers in 2008 at one-third the size of the original, reproduces 35 features of the iconic ballpark including the ivy, bricks, scoreboard and even a Harry Carry statue. Rather than 355 feet, it’s an even 100 feet down the lines – what would be a friendly distance to Cubs batters but even friendlier to Cardinals or Braves hitters facing Cubs pitchers.

Jane Addams Home & Grave, Cedarville
Americans cherish the humble origins of their presidents and civic heroes. The ultimate small-town girl, Jane Addams was the daughter of Quakers and founded Hull House in Chicago to improve the lot of immigrants. She also worked for reforms in labor laws and in 1931 was awarded the Nobel Peace Prize. The Cedarville Area Historical Society, housed in a former school built in 1889, displays Addams memorabilia including the bed where she was born in 1860.

Nearby is her childhood home, a Greek Revival-style brick structure. Local historian Jim Bade, 89, lives a quarter-mile away on the same street and can attest to the abiding interest in the reformer. “People drive by and shout, ‘Where’s the Addams home?’” he says. A film crew working on a public television documentary about Addams recently was in town, and Bade helped them connect with a local friend, 100-year-old Paul Fry, who served as a pall bearer for Addams’ funeral in 1935.

Stagecoach Trail Road, Lena
Hop off Rt. 20 in Lena and retrace the plodding journey of pioneers by stagecoach from Chicago to Galena. This gently curved, hilly road, dating back to the 1830s, offers pastoral scenery and small-town charms over its 40 miles. Blink and you miss Nora, once a bustling railroad town and now home to 112 souls. Warren hosts a popular pumpkin festival in September. Apple River Canyon State Park features remarkable limestone bluffs and stunning fall colors.

Charles Mound, near Scales Mound
The Illinois topography rises and falls majestically as drivers near Galena, and the state’s highest point is a mere 1,235 feet over sea level. But you can see three states from this hill, which is located on private property. It’s not exactly the view from the Sears or Hancock towers, but for Illinois it can hardly be topped.

Apple River Fort, Elizabeth
In 1832, aggrieved about the loss of his tribe’s land, Sauk leader Black Hawk and 200 of his braves attacked the Apple River Fort for nearly an hour. The fort was successfully defended amid two surprising developments. First, there was only one death. Also, the men had been on a journey, so a woman named Elizabeth led the fort’s defense. She became the namesake for the nearby settlement. The fort was torn down for lumber in 1847, but after its foundation and artifacts were rediscovered, it was reconstructed in 1996.

Long Hollow Scenic Overlook, near Elizabeth
The drive toward Galena, especially in the fall, is delightful. You pass small, tidy farms, grazing cows and thickly wooded areas. And you roll up and down hills. “It’s so unexpected. From New York on you’re on a flat road, and then you’re suddenly cutting through limestone and sandstone. The vistas are beautiful,” says Farr. One of the best places to stop and see the foliage is this postcard-worthy lookout.

Eagle Ridge Resort & Spa, Galena
No place better exemplifies the good life in Galena than this high-end resort, a gigantic welcome mat on Rt. 20. The complex is part of the sprawling Galena Territory, a 6,800-acre recreational, residential and resort community. About 100,000 folks annually come as guests to the resort, mostly for the luxurious spa, the beautiful grounds and the four golf courses. They stay at the well-appointed Inn or one of the 250 homes or townhomes. Remodeled, vastly expanded and debuting this fall, the Stonedrift Spa offers a wide variety of special services including sound healing, forest bathing and a Vichy shower.

Heralded by the International Dark-Sky Association, the grounds are especially conducive to stargazing. It’s only appropriate, then, that the spa now features a Biodynamic Lunar Glow Facial with ingredients that “harness the celestial energy of the cosmos.” And who couldn’t use a boost of celestial energy now and then?

U.S. Grant Home, Galena
Ulysses S. Grant triumphantly returned to his former hometown in August 1865 as a Civil War hero, and grateful Galena citizens gave him this furnished home, built five years earlier. Elected president in 1868, he only occasionally stayed here and last visited in 1880, five years before his death. Now run by the state, the home was restored in 1955 based on an illustration in an 1868 newspaper story. Much of his furniture remains. The imposing yet warm Italianate-style home features balustraded balconies looming over porches. Public tours take visitors through the home every Wednesday through Sunday.

DeSoto House Hotel
Galena is blessed with multiple charms: well-preserved, opulent architecture; vestiges of its boom time in the early 1800s; quaint shops and, most of all, the hilly streetscape with vintage storefronts.
Where to start? Start where Abraham Lincoln stood, the balcony where he delivered an important speech in 1856. The state’s oldest operating hotel, which still welcomes overnight guests and diners, later served as the presidential campaign headquarters for Grant.

Galena and U.S. Grant History Museum, Galena
If you missed the Civil War hero’s 200th birthday on April 27, 1822, an entrancing Grant hologram here will still greet you with characteristic gusto. Grant was known for regularly chomping on a cigar, and the museum duly displays his actual cigar butts as well as his boots and bow tie.

The museum’s most valued item is “Peace in Union,” the original painting by artist Thomas Nast depicting Lee’s surrender to Grant at Appomattox in 1865. The image has been a standard part of history textbooks for generations of American schoolkids, since a photo did not capture that moment.

Most of the museum, however, is devoted to Galena’s history. A current exhibit examines the history of African-Americans in Galena, many of whom were brought here by Southern slaveowners. Currently located in an 1858 Italianate mansion, the museum plans to break ground next year on a new, more accessible facility neighboring the Grant Home.

Like history itself, Grant is a curious, ever-shifting figure. Once considered a failed president because of the scandals of his associates, he now is more commonly regarded as a patriot and devotee of democracy.

“Every generation has its own take on him. He’s viewed now more positively,” says Tessa Flak, museum director.

Goldmoor Inn, Galena
Road trips need fuel. There’s hardly a better option than within the luxurious opulence of the Goldmoor, which overlooks the Mississippi and features seasonal menus and locally sourced food on its dining room menu. More than a dozen relaxing, well-appointed suites make this an appropriate place for an overnight stay.

River Boats in Dubuque
Life on the Mississippi, at least in this endearing Iowa city, is a good life. Tour boats, some reminiscent of the days of Mark Twain with their old-fashioned paddle wheels, leave or stop at the Port of Dubuque. The largest non-gaming riverboat on the Upper Mississippi is the Celebration Belle, a 770-passenger paddlewheel boat. A replica of a Victorian steamboat, the Riverboat Twilight has three decks, dining areas and sundecks. The American Lady offers a Colors of the Fall cruise.

Street Art, Dubuque
Nearly 40 new murals have come to adorn Dubuque since 2016. One of the best-known, a collage of flowers, is titled “Ada Hayden,” in honor of the Iowa botanist, educator and preservationist. A tribute to the working person, “Automate” depicts employees of the Dubuque Brewing and Malting Company. The nonprofit Voice Productions collaborated with local artists and acclaimed artists worldwide to craft the visually provocative murals.

National Mississippi River Museum and Aquarium, Dubuque
This is the most comprehensive and one of the best-ranked river museums in the nation. The Smithsonian-affiliated campus includes more than a dozen aquariums that feature river otters, octopi, turtles and creatures of not-so-deep rivers. The museum is not a mere showcase of animal life but operates on a “three-legged stool” model focusing on history, conservation and STEM.

Field of Dreams, Dyersville
It’s a slice of heaven for baseball fans who journey 25 miles west of Dubuque to the shooting location of the film “Field of Dreams.” The field is open year-round, with the farmhouse now serving as a bed-and-breakfast. Cornstalks hug the field until well into November.

Gramercy Park, East Dubuque
At journey’s end, double back to this small but mighty 10-acre city park located on a steep bluff above the Mississippi. Observe the 26 ceremonial and burial mounds from the ancient Hopewell culture, scour the sky for soaring bald eagles and catch a brilliant sunset. Here, the best of Route 20 reveals itself in the natural wonders enjoyed by the many generations who have settled this land.