2025 Diesel Truck Challenge Registrations Now Open!
2025 Diesel Truck Challenge Registrations Now Open!
When you come to Richland Center this October for the Diesel Truck Challenge, don’t miss the chance to experience all that Richland County has to offer. Nestled in the heart of Wisconsin’s Driftless Region, the area is full of rolling hills, scenic drives, and small-town charm. From outdoor adventure to unique shopping and dining, Richland County is the perfect place to make a full weekend out of your trip.
Make the most of your Diesel Truck Challenge weekend by stopping at Wild Hills Winery! Just minutes from Richland Center, this Driftless-area gem offers handcrafted wines and ciders, scenic vineyard views, and plenty of charm. Gather with friends for a tasting, stroll through the vines, and stick around for live music on Friday night—the perfect way to kick off your weekend in Richland County.
Round out your Diesel Truck Challenge weekend with a stop at Oakwood Fruit Farm, a family orchard that’s been growing in the Driftless hills for over five generations. Just east of Richland Center, Oakwood is a fall favorite, offering crisp apples, fresh cider, a bakery filled with local treats, and their legendary Apple Cider Donuts—a must-try! Stroll through the orchard, shop the retail market for seasonal goods, and take home a true taste of Southwest Wisconsin.
Looking for family fun during your Diesel Truck Challenge weekend? Chicken Ridge Farms is the perfect stop! Open September 20 through October 26, this seasonal favorite offers activities for kids of all ages, from an expanded corn maze and bean pit to the mega tractor tire sand pit and ultra slide. Families can also enjoy U-pick or pre-picked pumpkins, decorative gourds, and fall décor to take home. And don’t miss their pulled-pork sandwich—locals say it’s worth the trip all on its own. With plenty of space to play, explore, and make memories, Chicken Ridge Farms is a must-visit fall destination in Southwest Wisconsin.
Add a little Driftless flavor to your Diesel Truck Challenge weekend with a stop at English Prairie Distilling in Muscoda. This family-owned craft distillery was built on a passion for whisky, community, and creating a gathering place for locals and visitors alike. Using locally sourced ingredients and traditional methods, they craft some of the finest spirits in Southwest Wisconsin. During event weekend, you can expect more than just a drink stop—enjoy handcrafted cocktails and mocktails, plus live music in a welcoming atmosphere. Whether you’re a spirit enthusiast or just looking for a fun evening out, English Prairie Distilling is a must-visit.
No trip to Southwest Wisconsin is complete without a taste of its award-winning cheese, and the Original Carr Valley Cheese Factory is the perfect stop. Located just outside Richland County in Cazenovia, this nationally recognized artisan cheesemaker crafts a wide variety of cow, goat, and sheep milk cheeses that have gained fans across the country. Visitors can peek into the production facility from the retail area, watch a short video about the cheesemaking process, and, of course, sample their delicious creations. As Carr Valley’s very first factory, it’s a must-visit for foodies and cheese lovers looking to experience a true Wisconsin tradition.
Step back in time with a visit to Frank’s Hill, a sacred site overlooking the Wisconsin River Valley. This remarkable property, entrusted to the Three Eagles Foundation, features effigy mounds shaped like birds and animals, as well as a rare grouping of small conical “calendar mounds” believed to be over 1,000 years old. Built by the effigy mound civilization between 700–1200 A.D., these earthworks are a powerful reminder of Wisconsin’s ancient past. Visitors are welcome to walk the grounds, reflect, and take in the sweeping views of the Driftless landscape—but please be respectful and avoid walking on the mounds themselves. Considered sacred ground, Frank’s Hill offers a meaningful, educational, and awe-inspiring stop during your time in Richland County.
For outdoor enthusiasts, Miner Hill Trails Park—also known as Tower Hill—is a must-visit in Richland Center. Spanning 50 acres, the park features six scenic trails ranging from 1/5 to 4/5 of a mile, winding through wooded paths, open meadows, and past an old quarry site. Along the way, hikers will discover five overlooks, each offering railed views of the valley and panoramic sights of the city and surrounding countryside. Picnic areas and resting spots make it easy to take a break and soak in the Driftless beauty. Whether you start at Strickland Park with its playground and parking or connect via Tower Drive Trail, Miner Hill is a peaceful escape with something for all ages to enjoy.
Just north of Ithaca on State Highway 58, you’ll find one of the Driftless region’s most unique natural landmarks—Elephant Trunk Rock. Formed by centuries of erosion in the area’s Karst sandstone topography, this striking rock formation resembles the trunk of an elephant and makes for a fun photo stop. Located between Divine Lane and Jaquish Hollow Road, it’s an easy detour when visiting nearby attractions like Carr Valley Cheese or Oakwood Fruit Farm. Simple, scenic, and uniquely Driftless, Elephant Trunk Rock is a quirky must-see along your Richland County journey.
Discover one of Richland County’s most unique natural landmarks at Pier County Park in Rockbridge. Donated by the Pier family, this 10-acre park is home to a striking half-mile sandstone “finger” rising nearly 60 feet above the valley floor, topped with pines and lush greenery. At its base, the West Branch of the Pine River merges with the Main Branch, creating a dramatic Natural Bridge that visitors can explore by walking through a man-made tunnel carved into the rock. Stairs also lead to the top, where panoramic views of the Driftless landscape await. In addition to its natural beauty, the park features two historical markers—one highlighting the unique rock formation and another commemorating the Blackhawk Wars. With six campsites, picnic shelters, grills, play equipment, and riverside scenery, Pier County Park is both a geological wonder and a relaxing spot for camping or day trips.
Rising abruptly from the Driftless landscape, Steamboat Rock is one of Richland County’s most iconic natural formations. Located just north of Richland Center near the intersection of Steamboat Hollow Lane and County Road SR, this sandstone bluff stands tall and apart, resembling the bow of a steamboat cutting through the valley. Especially striking in the fall when surrounded by colorful foliage, Steamboat Rock is a quick and memorable stop for visitors exploring the area. Whether you’re passing through on your way to other attractions or simply looking for a scenic photo opportunity, this natural landmark is a Driftless favorite.
For even more ideas on things to see and do during your visit, be sure to check out the Greater Richland Area Tourism website, created by the Greater Richland Area Chamber of Commerce. It’s a one-stop resource for local attractions, dining, lodging, and events, helping you make the most of your time in the Driftless region. Whether you’re planning your Diesel Truck Challenge weekend or looking to explore beyond, the site is filled with inspiration to guide your adventure.
Click here to see a full event schedule and/or pre-register to participate.
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