There’s something about a fall road trip that brings out the best of Wisconsin. If you’ve experienced one, we bet you remember it. Acres and acres of brilliantly colored forests, seasonal farmers’ markets and roadside stands around almost every corner — fall in Wisconsin is unforgettable. Perhaps it’s the fall festivals like La Crosse’s Oktoberfest, Prairie du Chien's Oktoberfest or the Warrens Cranberry Fest. Or maybe it’s the fascinating, one-of-a-kind attractions and charming, history-filled villages that dot our scenic byways and rustic roads.
Whatever the reason, fall color touring in Wisconsin is an experience that can’t be duplicated in any other state. So, fill your car with the family or friends — here are two of the state’s best auto and motorcycle driving tour itineraries for the fall season, tracing two of the state’s signature rivers – the Wisconsin River and the winding Mississippi, along the Great River Road.
Wisconsin Scenic Byway: State Highway 60
The first corridor to be designated a Wisconsin Scenic Byway, Highway 60 takes us 100 miles along the Lower Wisconsin River from Lodi to Prairie du Chien in the heart of southwest Wisconsin’s pastoral Driftless Area. Be sure to visit the Lower Wisconsin River Road Scenic Byway website for additional information. Our 2-day itinerary covers our favorite stops along this drive under the fall-colored leaves.
Day One: Prairie du Sac, Spring Green
Beginning 40 minutes northwest of Madison near Prairie du Sac, this scenic fall route starts with a tour and tasting at the Wollersheim Winery. Founded in 1972 by the Wollersheim family, the winery continues to expand and grow their operations. They’ve won numerous awards for wines such as the top-selling Prairie Fumé as well as seasonal fall wine favorites. Attend a tour and you’ll taste Prairie Fumé and other wines. We recommend sitting down with a glass together — you’ll have lots to talk about with everything ahead on your journey. And don’t worry, it’s not day drinking—it’s day tasting.
Head 40 miles west, and we find ourselves in the artsy enclave of Spring Green, the next stop on our journey. Here, we find the sprawling estate of America’s most famous architect, Frank Lloyd Wright. Wright’s Taliesin, a national historic landmark, is often called his “self-portrait.” The site of several fires (including one during which his mistress and several others were murdered), Taliesin was continuously rebuilt and expanded by Wright well into his final years. Tours of Taliesin and several other estate buildings are available throughout the fall, but be sure to book your tour online well before your visit.
Just down the road from Taliesin is the equally fascinating attraction known as House on the Rock – a must see during any scenic tour in fall. Built by the eccentric Alex Jordan, the Japanese-style home is both an architectural attraction and a museum complex of strange, unrelated collections. The house’s 218-foot suspended “Infinity Room” is even more spectacular in the fall with the trees of the Wyoming Valley ablaze in fall color, 165 feet below the room’s glass floor. The view is a family-favorite — and makes for a great family selfie — while the variety of exhibits means there’s something for everyone. House on the Rock offers several self-guided tours through displays of antique weapons, dolls and dollhouses, a million-piece miniature circus, the world’s largest indoor carousel and more. You’re sure to be talking about this stop for years to come.
Located between House on the Rock and Taliesin is the House on the Rock Resort. Another stunningly designed building, Frank Lloyd Wright’s influence is seen throughout, particularly in the two-room suites that offer panoramic views of the countryside in full fall color. While at the resort, take advantage of the Grandview Restaurant known for its American regional cuisine. If there’s extra time, check out the Resort’s top-notch spa or golf course.
Day Two: Boscobel, Wauzeka & Prairie du Chien
Boboscel, the next stop on our fall drive, is just 40 miles west of Spring Green. The Boscobel Heritage Depot Museum, a reconstructed railroad depot, combines railroad-related artifacts with historic facades of buildings that once lined Boscobel’s main street. Experience together what life was like during the turn of the 20th century before heading to our next stop in Boscobel.
Like many of the towns along the picturesque, sandbar-filled Wisconsin River, Boscobel is home to a canoe and kayak outfitter. Located in a refurbished 1840’s feed mill, Wisconsin River Outings is one of the best in the region and arranges river excursions lasting from several hours to several days. In addition to guided outings throughout the fall season, their friendly team rents canoes and kayaks for visitors to use sans guide and they’re happy to share local knowledge on everything from river currents to sandbar locations. Whether you’re there to paddle or just check out the building’s history, you’ll be glad you stopped here, your friends or family will be glad you stopped here.
For the end of this 2-day fall color journey, we’re going all the way to the end of the road. State Highway 60 ends just north of where the Wisconsin and Mississippi Rivers meet, at Prairie du Chien. A town recognized as the state’s second-oldest community, Prairie du Chien’s origins go back to the nineteenth century fur trade. If the group is down for camping: we recommend camping at Wyalusing State Park. One of Wisconsin's oldest parks, Wyalusing features spectacular river vistas, as well as Native American burial mounds, a canoe trail, bird watching, fishing and boating. The setting is unforgettably picturesque in the fall and the perfect way to end your trip, with s’mores, stars and quality time together.
National Scenic Byway: Great River Road
Wisconsin Highway 35, paralleling the Mississippi River from Kieler to Prescott for 250 miles, is part of the Great River Road National Scenic Byway, voted one of America’s “10 Most Scenic Drives” by the Society of American Travel Writers. In Wisconsin, the route is marked by steep, forested valleys and coulees, as well as soaring limestone bluffs with stunning views. Add fall color to the mix, and you have a road trip you, your friends and your family will never forget. We’ve curated this 3-day itinerary so you’ll get the most out of our Great River Road.
Day One: Potosi, La Crosse & Onalaska
Fall travelers: start this scenic journey at the National Brewery Museum in Potosi. Located in a restored 1852 brewery, Potosi’s unique history helped it beat out famed brewing cities like Milwaukee and St. Louis to host the museum. While the beer is for those ages 21+, our beer culture—and this museum—is for everyone. Exhibits include interactive model trains, trucks and race cars in addition to displays filled with historical memorabilia, all telling the story of beer, breweries and breweriana.
The Potosi Brewing Complex is also home to an operating brewery, brewpub and beer garden. So enjoy a sip and bite while talking about all that’s to come on your adventure before heading to the next destination on our fall road trip.
Next stop: Prairie du Chien, the oldest European settlement on the Upper Mississippi River. This great river town has many frontier stories to tell. We love it so much that we snuck it into both of these fall road trip itineraries! In addition to Wyalusing State Park mentioned above, we recommend touring Villa Louis, a Wisconsin Historical Society site, where you can see the furnishings and Victorian lifestyle of the Dousman family, one of the state’s first millionaire fur traders. The kids especially will love imagining themselves living during Wisconsin’s past.
After a busy day of immersive brewery and frontier history, it’s time to relax in Onalaska, just north of La Crosse, with a stay at the Travel Green Wisconsin-certified Rainbow Ridge Farms B&B. Rainbow Ridge Farms is a charming turn-of-the-century working farm nestled in a peaceful valley that explodes with fall color, and it’s sure to make great memories for your friends and family.
Day Two: La Crosse & Trempealeau
What better way to experience the romance of the Mississippi River and the beauty of the fall color season than aboard an authentic paddlewheel river boat? The La Crosse Queen, a modern-day replica of the grand river boats that plied the Mississippi in the 19th century, offers sightseeing and dinner cruises. The Queen is one of the few authentic Mississippi River paddlewheel river boats still in operation, and it’s an experience your friends and family will remember forever. Tours board at Riverside Park in historic downtown La Crosse.
Time your road trip to experience another famous LaCrosse highlight: Oktoberfest. It’s one of the largest Oktoberfest celebrations outside of Germany. Held each year from the last weekend of September through the first weekend of October, the festival attracts nearly 150,000 people with German music, entertainment, ethnic food, arts, parades, boat rides and of course, beer. Even if you don’t make it to Oktoberfest, there’s much more to see and do, including the next stop on our fall journey.
Sixteen miles north of La Crosse, stay overnight at The Historic Trempealeau Hotel in Trempealeau. A 1871 building that was extensively restored in the mid-1980s, the hotel offers European-style rooms, Jacuzzi suites, a sun deck, beer garden and restaurant. Insider tip: order the vegetarian walnut burger. It’s become a regional legend. Made of ground walnuts mixed with Wisconsin cheeses, onions, tamari, eggs and various spices, the burgers have become so popular that they’re now in stores and other restaurants throughout the Midwest.
Day Three: Alma, Pepin & Stockholm
Follow Highway 35 north another 45 minutes to the quaint river town of Alma. What makes it so special: the entire town is now listed on the National Register of Historic Places because so many of the community’s historic buildings have been beautifully restored. Sandwiched between the Mississippi River and the 500-foot limestone bluffs behind the town, Alma is seven miles long, but just two blocks wide. Be on the lookout for swans, and be sure to point them out to your fellow travellers — Alma draws national attention from birdwatchers every fall during the Alma Tundra Swan Watch. Throughout late October and early November, birders gather at the Rieck’s Lake Park Wildlife Observation Platform where the majestic swans make one of their only stops during their annual migration from northern Canada to the Chesapeake Bay area.
Fifteen miles north of Alma, Pepin is the birthplace of Laura Ingalls Wilder, the famed author of the “Little House” books. The village honors the writer’s life and work with the Wilder Museum and a replica of her log cabin. Whether you’ve read the books, watched the show or not, we know the friends or family will enjoy immersing themselves together in this iconic American treasure.
Pepin is a regional draw for sailors, water skiers and other boating enthusiasts, many of whom dock at Dan’s Pepin Marina on this two-mile-wide stretch of the Mississippi. Transient boaters and locals alike swear by The Pickle Factory restaurant. Located next to the marina and overlooking the lake, it’s the ideal place to enjoy homemade onion rings and BBQ pork ribs while taking in the ephemeral fall colors. You’ll have lots to talk about over your meal: all of the memories you’ve made along this journey.
Downtown Stockholm - Stockholm
We’re ending our fall road trip with a town you won’t want to miss. Seven miles north on Highway 35, you’ll find the artsy village of Stockholm. Although its population is less than 100 people, Stockholm boasts an impressive Main Street of original art galleries and culinary attractions that rival large cities. Don’t miss the made-from-scratch Wisconsin Cherry Pie at the Stockholm Pie Company or learn how to cook (and find) wild morel mushrooms at the Palate Gourmet and Kitchen Store. The town is also home to a number of eclectic artists and artisans, whose works are featured in the Antique Future, The Purple Turtle Artisan Collective and Northern Oak Amish Furniture.
Last but not least, on any fall trip, it’s important to stay up-to-date on leaf color conditions so you make the most out of your journey. Our Fall Color Report will keep you in the know about peak color in real time wherever you go in Wisconsin. And for even more fabulous fall rides, check out the best fall drives in southern Wisconsin.