Adventures on the Trail in Southern Wisconsin

Imagine stumbling upon a hidden gem where history and community spirit embrace you at every turn, a place that radiates friendliness and a welcoming vibe. That’s exactly what we discovered when we rolled into Darlington, Wisconsin. Nestled within the rolling hills of Lafayette County, this quaint town of just over 2,500 residents might seem like just another small Midwestern town at first glance. However, as we cruised along Main Street, Darlington’s unique charm and rich history began to unfold. Banners strung across the street, announcing the town’s upcoming 175th birthday celebration fluttered in the wind, while signs for “Tunes at Twilight,” a summer outdoor concert series featuring local bands, showcased the community’s pride and vibrant culture. The historic district, with its well-preserved storefronts lining both sides of the street, evoked a warm sense of nostalgia, making it clear that Darlington is far more than meets the eye.

Adding to its allure, Darlington is situated along the Cheese Country Trail, one of many scenic ATV/UTV routes that crisscross the rolling countryside of southern Wisconsin, drawing enthusiasts from near and far. These trails, many built on abandoned railroad beds, connect various towns and villages throughout the region, offering a unique way to explore the area. Adventurers can traverse the countryside by day and choose to spend nights in local hotels or campgrounds. The 47-mile-long Cheese Country Trail, in particular, makes Darlington a popular hub for ATV/UTV enthusiasts.

The City of Darlington offers a convenient campground alongside the Pecatonica River, just two blocks from Main Street with its local shops and restaurants. This location is also ideal for visitors seeking easy access to the Cheese Country Trail and is particularly popular with the off-road community on weekends. When we arrived, we found that recent rains had caused the river to overflow, flooding much of the campground. Fortunately, our reserved site was on higher ground, so we were able to set up camp without any issues. The campground was relatively peaceful in the afternoon, as most campers were out exploring the trails. However, as the sun began to set, the rumble of ATV/UTV’s started to reverberate throughout the area.

Our visit to Darlington was particularly special because Grammi’s cousin and his wife had invited us to join them on one of their UTV trips—a welcome break from their busy farm life. They often escape to the trails for a few days of adventure, and we had been eagerly anticipating joining them this summer. This would be our first UTV adventure, and the excitement was palpable. We were thrilled to ride alongside Grammi’s cousin, knowing his experience and familiarity with the trails would make the experience even more unforgettable.

Arriving a few days early to acquaint ourselves with the area, we had some extra time to explore the region on our own before the big ride. On Sunday, we decided to take a trip south to Galena, Illinois. Known for its well-preserved 19th-century buildings and vibrant business district, Galena is a popular weekend destination. However, it seemed we weren’t the only ones with that idea—the town was bustling with visitors, and it took us three laps around the downtown area before we found a parking spot, albeit an attended lot for twenty bucks.

Galena is a treasure trove of history and culture, and we spent hours weaving in and out of the numerous shops and galleries that line the streets. Despite the crowds, the town’s charm was undeniable, with each shop offering unique and interesting finds. For lunch, we struggled to decide which of the many dining options to try. We eventually opted for a bowl of seafood chowder at Embe Eatery and Lounge, which was every bit as delicious as we’d hoped.

After lunch, we made our way up the hill to the Galena-U.S. Grant History Museum, a captivating place that delves into the rich history of Galena while honoring its most famous resident, Ulysses S. Grant, the 18th President of the United States. The museum is filled with intriguing artifacts and exhibits that offer a glimpse into the past, including treasures like the “Peace in Union” painting, the “General Grant on the Battlefield” painting, and the flag from the Vicksburg Siege. It’s a must-visit for history buffs and anyone interested in the legacy of this historic town.

Galena-U.S. Grant History Museum sits one block off of Main Street on Bench Street.

After returning to Darlington that evening, we were excited to attend the “Tunes at Twilight” show. Unfortunately, we discovered only after arriving at the original outdoor venue that the event had been moved indoors due to the threat of inclement weather. By the time we found the new location, the band was already on its final set. We could hear the music spilling out onto the street and listened from a distance for a few minutes before driving back to our camper. Although missing the show was a bit of a letdown, it didn’t dampen our spirits.

Monday morning arrived with an eerie quiet. As I sipped my coffee, the only sound was the clip-clop of horse hooves as an Amish buggy trotted through town, eventually vanishing over the hill. With the weekend crowd gone, there was only one other camper in the campground. Grammi and I enjoyed a relaxed morning before strolling down Darlington’s Main Street to explore the shops and to see what was open for lunch. That evening, we took a bike ride around the park and found the Cheese Country Trail that runs through town. On Tuesday, we drove through the countryside, admiring the Amish farms in the area.

Grammi’s cousin and his wife finally arrived on Tuesday. We met them for dinner at the Cork Down Saloon, just a short drive from Darlington. It’s one of their favorite watering holes, known for its lively atmosphere and good food. While there, we also met their friends and enjoyed some drinks and a delicious meal as we planned our next three days of trail adventures.

Since we don’t own a UTV, we reserved a rental from Mike’s Engine Works, a local shop that offers a variety of off-road vehicles for rent. Although ours had less power and fewer accessories than those of our riding companions, it was perfectly adequate for our needs, though I was not a fan of the Pepsi blue color. Our plan was simple: spend the next three days following Grammi’s cousin, his wife, and their friends as we explored the trails and towns of the area.

Darlington became our launchpad for those three-days exploring across diverse landscapes and charming towns. Each day, we traversed winding trails—from rugged, dirt paths to smooth, paved roads, and even narrow two-track farm trails with deep ruts and steep cattle grates. These unique obstacles increased our heart rate and heightened the adventure as we marveled at the stunning scenery.

We discovered a profound sense of freedom that comes with trail riding. There’s something exhilarating about bouncing along a dirt path, immersed in the sights and sounds of nature, with nothing but the open trail ahead. One particularly special moment was spotting a doe nursing her fawn right on the trail in front of us. We stopped so not to disturb the intimate scene and watched until they moved off into the brush. The terrain varied with each mile, from wide-open cornfields and dense woodlands to the bustling streets of small towns. We even climbed a few hills, where we were rewarded with expansive views of the rolling landscape.

Yet, our journey was about more than just the routes. One of the true joys of trail riding in this region was the chance to uncover small towns that might otherwise be missed. These stops offered a delightful break—perfect for stretching our legs, exploring local sights, and enjoying a meal or a cold drink. Each town revealed its own unique character through lovely town squares, local eateries, friendly bars, charming shops, and even intriguing museums. These experiences provided a deeper glimpse into the history and culture of southern Wisconsin, making our adventure both scenic and culturally enriching.

Grammi’s cousin provided the guidance and expertise we needed, making the experience stress-free. Riding along with them ensured we didn’t get lost or accidentally turn onto roads that aren’t ATV/UTV-approved. With all the turns and different trails we crossed, I’m not sure I could retrace our route—or even recall all the places we stopped during those three days. The pictures below, hopefully, highlights the most memorable places and moments.

Day 1

After a hearty breakfast at Glennies, located on Main Street in Darlington, we headed north on the Cheese Country Trail.

We rode along an old railroad bed, crossing bridges, highways and dusty trails.

We came across an Amish stand with maple syrup, jam and preserves. Purchases were made on the honor system by dropping the money in a slot.

We went to Lancaster and stopped at Zippy’s Brass Rail for lunch. Afterward, we toured the Grant County History Museum.

The First Capital Historic Site, located just outside Belmont, is listed on the National Register of Historic Places. Since it was along our route, we took a few minutes to explore the area and admire the historic buildings. Established as Wisconsin’s territorial capital in 1836 by the governor, its role as the capital was brief. Opposition to the location led to the capital being moved to Madison soon after.

As we ended Day 1’s adventures, Grammi got her turn at the wheel.

Day 2

On Day 2 we went south on the Cheese Country Trail prompting Grammi to say “new territory.”

We learned the history and techniques of cheese making at the National Historic Cheesemaking Center Museum in Monroe.

Staying with the cheese theme, our Day 2 lunch spot was at Baumgartner’s Cheese Store and Tavern in Monroe where we sampled the cheese curds.

We concluded our days ride at Hawk’s Mill Winery before making the drive back into the low glaring sun.

Day 3

The morning began just like the previous two with breakfast at Glennies. We bid farewell to the friends of Grammi’s cousin, as they headed back to the farm, leaving just four of us for Day 3’s adventure.

We made a quick stop at Shake Rag Alley. For a Friday morning, there wasn’t much going on. Regardless, we took a look around.

We rode the trail into Mineral Point, a historic town established in the 1830’s by Cornish immigrants. There were many well preserved buildings with plaques noting their presence on the National Register of Historic Places.

Since we were in another Cornish mining town, it was no surprise to find a restaurant serving pasty. The Red Rooster Café, located in the historic district, is a third-generation family-owned restaurant that has been serving pasty for over fifty years. My friends in the U.P. may not like to hear this, but the pasty in Mineral Point was just as good as any I’ve had in Michigan.

Before leaving Mineral Point, we toured the Gundry House built in 1868. It is maintained and operated by the Mineral Point Historical Society. We also toured the Mineral Point Railroad Museum.

Friday night fish fry is a big deal in southern Wisconsin. No matter if fish is typically on the menu or not, it is on every restaurant’s menu come Friday. Even the local pizzeria served fish on Fridays. We ate our fish dinner at Fayette Saloon.

As Saturday morning rolled around, we packed up the camper and slowly made our way out of town. Crowds were gathering for a pancake breakfast at the firehouse, and food trucks were setting up in the park. A farm tractor pulling a wagonload of people passed by, with a guide pointing out the town’s historic sites. The 175th anniversary celebration of the town’s founding would continue into the evening. While part of us regretted missing the festivities, we were also relieved to avoid the crowds.

To sum up our time in southern Wisconsin with one word, that word would be “fun”. We had a blast trail riding with Grammi’s cousin and his wife. From the dusty trails to the historic towns, it was an exciting time we shall not soon forget. We hope to do it again someday.

Until next time—happy days and safe travels.