A ride back in time in beautiful Galena Country, Illinois

by Brett Rothmeyer

This article is brought to you in partnership with Galena Country Tourism. Follow the link to learn more about our sponsored content policy.

Photos and video: Michael Dillon | Words: Brett Rothmeyer

When it comes to cycling destinations, the midwest of the United States is not often at the forefront of a cyclist’s mind. Still, a few small towns connected in a region known as the “Driftless Area” are starting to sway where riders choose to spend their time on the bike.

Unlike most of the midwest, the Driftless Area never experienced glaciating during the last ice age, which spared the region the geological act of “drifting” from glaciers. Instead, the land of the Driftless was shaped by small rivers on their way to feed the Mississippi, leaving the undulating terrain that remains today. 

Just off of Illinois State Route 20 sits the small town of Galena, appropriately named for the mineral that was extracted from the earth around it and nestled on the banks of the river sharing the same name. Located in the furthest-northwest county of Illinois, Galena’s 19th-century buildings seem to be preserved in a time long since passed.

Walking through the steel flood gates on Main Street, it takes little imagination to visualize the ghosts of the past on a rainy Tuesday evening. Even after several devastating floods, the architecture of Galena remains a living exhibit of the town’s mining and railway boom of the 1820s.

Our visit to Galena began with a quick dinner with our guide James Hillis at the Embe Eatery & Lounge. Hillis’ enthusiasm for the region began while looking for new routes and quiet roads while living in Chicago. Having felt like he had experienced as much as he could on two wheels in the Chicago Metro area, Hillis would escape the city as early as 4:30 am and head for Galena. “Fueled on gas station coffee,” Hillis explained that the prospect of new and interesting routes far outweighed the sacrifice of sleep on the weekend.

After visiting Galena regularly to ride, Hillis eventually called the small town home, and lives just a few miles from Main Street. With James’s extensive knowledge of regional history and what would appear to be a built-in atlas of the area’s farm roads, we were looking forward to our time with him, despite the weather forecast for the days ahead. 

The first morning greeted us with rain and grey skies but also the addition of Ellen Noble to our group. Noble is a multiple-time US champion in the discipline of cyclocross and no stranger to adverse weather conditions. After dashing a few last-minute mechanical scares, we were off to Big Bill’s for a bonus cup and a breakfast sandwich to fuel the day’s endeavors. 

Just a short drive out of town is Apple River Canyon State Park. A secluded little park along the banks of the Apple River, it hosts a network of wooded hiking trails and a serene setting for a picnic or a lazy day of reading by the river. For our purposes, the park was a perfect launching point directly to an incredible route.

As you can imagine, starting a ride in a canyon means going up. While Ellen and I felt the tightness of a day of travel, James cheerfully spun up the climb giving us a quick rundown of where we were headed and what to expect. 

The rain became light and steady, creating an almost calming effect. The wet dirt under our tires crackled amongst the chirping of birds, and the farm pastures took on an oceanic disposition. It’s easy to see why James fell in love with riding here; mile after mile, the roads undulate in peace, only interrupted by a deer startled by the roadside or a horse braying at a distant barn. The air temperature was agreeable enough that even the rain had enchanting properties to it; however much the crunching of our drivetrains disagreed.

The silhouettes of abandoned farm properties were only further enhanced by the fog rolling through the wet valleys and James’ recanting of famous crime scenes and supposed spirits let adrift in the area. Alas, the day was not without a victim – James’ crank arm virtually cracked in half, leaving Ellen and myself to fend off the rest of the route, weather, and any revenant beings that happened to be out there.  

During our first 24 hours in town, heavy with rain and sandwiches, we headed for Bread & Vine for salads and back to the hotel for an early night’s sleep. There was the promise of an early morning void of precipitation and a second helping of perfect “Driftless” terrain on tap.

Awake with the dawn, we shuttled east on Route 20 to the even smaller town of Elizabeth for the day’s starting point. As promised, the roads and sky were dry for the time being, and within an instant of leaving the community park’s lot, we were back on perfect country lanes by way of West Street.

Day two of riding was filled with an abundance of cattle farms and roads that held the same names that were displayed on the mailboxes. James explained how many of the family farms in the area were established by settlers pushing west and have remained generational amongst the namesakes. 

While most of the area’s natural ecosystem has been altered for agriculture, there is a handful of preserved midwestern oak savanna in the region. The twisted native oaks shading the tall grass allow passers-by the ability to visualize what this land once was.

The abundance of wildlife and natural resources allowed the tribes of the Mesquakie, Ho-Chunk, Sauk, and Menominee to thrive in the area prior to the arrival of Europeans. It was these same tribes that found a use for the mineral galena and were the first to begin to mine it before the boom and federalization of the land. 

The rain eventually found its way back to us, but at a much lighter rate than the soaking of the day before. There were several examples of pristine Americana along the way, a few pick-ups from the 1950s in various states of decomposition, barns housing archaic farm equipment (the barns’ wooden slats having shrunk over time, revealing the secrets of their confines), and the occasional old-timer in a pick-up with his dog in tow.

The farm relics weren’t the only highlights of the day; two steady climbs on both South Grass Road and Gamble Hill Road certainly primed us for lunch back in Elizabeth.

Over sandwiches and one gargantuan pickle at Lola’s Deli, we recalled our favorite parts of the last two days and planned for our third and longest day of riding. The weather apps were all calling for the sun the next day but we had our suspicions. 

The swan song for our few days of riding in Galena began properly from Main Street after some pastries and much-needed caffeinated beverages from Trolley Depot Coffee and Tea. We entered a bizarro world when James introduced us to a few co-workers and friends, one of whose name just happened to be Rose Ellen Noble, a mirror to our riding partner Ellen Rose Noble.

Rose Ellen and Ellen Rose discussed at length the origin of the family name, and it was determined that they were, oddly enough, not related. Meanwhile, I wondered if this whole scene wasn’t some metaverse setup. It was, however, interesting to learn how each of them arrived at living in Galena. While each of the arrival stories varied, the consensus was that the slow pace of country living suits them all just fine, as well as it did us.

Once on our bikes, and on the first section of empty dirt farm road, James was quick to note that this was his “route home from work when he rides.” A fact, but also perhaps a subtle brag as he explained the normal seven or so mile commute can easily extend into 17 and so on. There were a fair number of roads with “Hollow” and “Canyon” attached to their names, offering up some decent climbing for the day.

A few stretches of gravel pitches had been freshly dragged, much like one does to a baseball field to freshen the dirt. While perhaps this was appropriate road care for the area, it made the already power-zapping gravel track feel like a pit of molasses. Thankfully the dragged roads were not plentiful, but the climb up Headquarters Road was particularly difficult. Following some soft tire tracks up the steep grade was the only way to keep the bike from sinking into the spongy dirt and coming to a halt. 

The elusive sun finally made an appearance for the last few miles of our day, justifying the summer kit I had picked out. The final route that James treated us to was a fitting send-off as it highlighted some of the best of what Galena has to offer. The rural terrain, the horses, the cows, and some of the newer homes being built in the area were all a great glimpse of what is going on in Galena.

By the time we had found our way back to Main Street, the weekend visitors were starting to roll into town. The parking spaces were filling up along with tables in the restaurants and bars. With a summer day revealing itself to us, we took a bit of a bonus meander down the bike path from town to the Mississippi River.

Four miles along a secluded rail-to-trails path, there are remains of the old lead mines on the hillside. The trees parted to reveal the still waters of the vast Mississippi. Its stillness underplays the importance it has played in the history of the United States, both culturally and logistically.

Summer was just starting, and the bugs were already at a full hum by the river’s bank; I pestered James with a question about ship traffic and how things must have appeared in the 1800s. He was happy to amuse me with the history of the waterway and its impact on Galena. 

Riding in Galena re-sparked my love of proper road riding. Riding out of my front door and just seeing where the roads would take me was how I fell in love with cycling. The introduction of smartphones and the increased hostility of drivers around my home city have left me daydreaming of long outings on the bike not interrupted with near-death experiences, or words shouted from a window cursing my existence. Galena gifted those long outings to us.

Pedalling on the roads of Galena felt like taking a trip back in time in more ways than one. We encountered very little traffic, and the drivers of the few cars that we did encounter all nodded and waved in our direction. Whether the salutations were out of kindness or confusion about what we were up to, it was a welcomed change.  

If you find yourself in and around the midwest and you are hungry for some proper riding, I wouldn’t hesitate to swing through Galena, IL, and pick up a map. If something a little more organized is needed, the annual Ten Thousand ride generally takes place around the end of May or early June, offering up a few routes of varying lengths, the longest being over 200 miles / 320 km (gulp.)

What you need to know

Getting here

If you’re flying into the area, catch a flight to Dubuque Regional Airport, Iowa. From there, it’s a scenic 30-minute drive to Galena, along US Highway 20 and across the Mississippi River.

If you’re coming from Chicago, follow US Highway 20 west for two and a half hours. O’Hare International Airport services the Chicago area.

The climate

Galena Country offers visits something special in every season:

Spring: Cool and wet with lots of wildlife (average temperature 58 º F / 14 ºC).
Summer: Hot and humid. Be sure to hydrate and bring bug spray (83 ºF / 28 ºC).
Fall: Cool and breezy but the best fall colours (61 ºF / 16 ºC).
Winter: Chilly with snow-covered roads. Wind chill makes it feel even colder. (31 ºF / -1 ºC).

Wildlife and farmlife

You’re sure to see plenty of animals during your visit to Galena Country. Deer, wild turkey, bald eagles, foxes, bobcats, and coyotes can all be spotted in the wilderness. On the many farms you’ll ride past, you’re bound to spot horses, donkeys, goats, sheep, chickens, pigs, and of course, cattle. (The county has the most cattle of any county in Illinois with more than 50,000 cows).

Nearby bike shops

If you’re looking for a last-minute tune-up or to grab some supplies for your cycling adventure, check out the following bike shops in nearby Dubuque, Iowa:

Cycling tour guides

Looking for a guided riding tour of the Galena region? The team at Galena River Outfitters offer tours for beginner cyclists.

Food and drink

The team at Visit Galena has pulled together a bunch of helpful guides about all the great eating and drinking options in the area. Here’s everything you need to know and here are a few choice articles from within that selection:


There’s plenty to do in Galena Country besides head out on an amazing bike ride. Again, the team at Visit Galena has pulled together some info to make your visit easier and more satisfying. Check out the region’s “Things to Do” page as a great starting point, or check out the guides below:

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