Exploring the Heart of Mississippi River Country

EXPLORING THE HEART OF MISSISSIPPI RIVER COUNTRY: A SCENIC ROAD TRIP THROUGH MINNESOTA, WISCONSIN & ILLINOIS
By Melody Pittman

After wrapping up the always-exciting IPW travel writers conference in Chicago, I embarked on a 4-day adventure that was nothing short of unforgettable. Along with eight international journalists, I explored Mississippi River Country through parts of Minnesota, Wisconsin, and Illinois—states I rarely visit, making this the perfect chance to see a new side of the Midwest.

ON BIG BLEND RADIO: Travel writer Melody Pittman shares highlights from her scenic and delicious road trip through the heart of Mississippi River Country, covering memorable stops in Minnesota, Wisconsin, and Illinois. Watch here in the YouTube player or download the episode on Podbean.

If you love scenic views, small towns with big personalities, and world-class attractions mixed with rural charm, keep reading—this journey might inspire your next road trip!

Day 1: Big City Vibes & Natural Wonders in Minneapolis, Minnesota
Our adventure began in Minneapolis, where the Minnesota River meets the mighty Mississippi. First up: the Mall of America (in Bloomington), a destination in itself. With 420+ stores, an indoor Nickelodeon Universe theme park, a bounty of restaurants, and no sales tax on clothes or shoes, it’s easy to spend a whole day exploring. The AC Hotel Bloomington, where we overnighted, is steps away from the mall.

After a bit of shopping and sightseeing, we enjoyed a guided driving tour of the city.

Two standout stops:
* Minnehaha Falls – A breathtaking 53-foot urban waterfall.
* Spoonbridge & Cherry – A must-snap photo-opp at the Minneapolis Sculpture Garden.

That evening, we dined at Borough, my favorite restaurant of the entire trip. The food was phenomenal (Squash Tartine 10/10), the ambiance stylish, and the flavors memorable. We capped the night off with a free, family-friendly water ski show by the Twin City River Rats—an impressive and uniquely Minnesotan way to end the day. (Tip: bring a lawn chair or blanket.)

Day 2: Mississippi River Magic in Red Wing, Wabasha & Winona
The next morning, we ventured into Minnesota’s Bluff Country, where the Mississippi River carves a dramatic path through hills and valleys.

Red Wing was our first stop, home to the Pottery Museum of Red Wing, Hanisch Bakery, and a trolley tour that offered a historic glimpse of the city.

In Wabasha, we visited the incredible National Eagle Center, where we learned about eagle conservation and saw a few majestic birds up close. Lunch bowls were from HERB + ARROW, a delightful local spot with fresh choices.

A scenic photo stop at Hok-Si-La Park gave us panoramic river views before we arrived in Winona. There, we explored the Minnesota Marine Art Museum, a world-class treasure that far exceeded expectations with works from Van Gogh, Monet, and beyond. Dinner at Signatures Restaurant was a real treat, and we overnighted at AmericInn Winona.

Pro tip: Don’t leave Winona without grabbing a sweet treat from the legendary Bloedow Bakery. Their famous Long Johns have been satisfying locals for 100+ years!

Day 3: Wisconsin’s Driftless Region & Capitol Charm
Crossing into Wisconsin, we spent the day in the Driftless Region, a unique geological area that escaped glaciation, resulting in stunning rolling hills and winding roads.

Our first stop: Taliesin in Spring Green, the UNESCO-recognized estate of iconic American architect Frank Lloyd Wright. We enjoyed delicious sandwiches at the Riverview Terrace Café, followed by a fascinating guided tour of Wright’s eclectic home and studio. Whether you’re a fan of architecture or love beautiful places, Taliesin is a must-see.

We then traveled to Madison, Wisconsin’s capital city, where we checked into the Best Western Premier Park Hotel, across from the historic Wisconsin State Capitol Building—and what a view! The granite dome is one of the largest in the world and positively gleams in the sun and moonlight.

In Madison, we also:

* Had ice cream at Daily Scoop, part of the University of Wisconsin–Madison’s riverfront Memorial Union Terrace

* Sampled cheeses at Fromagination, a boutique cheese shop that takes tastings seriously

* Enjoyed a delectable dinner at Graze, led by James Beard Award-winning chef Tory Miller

Day 4: Illinois Highlights — Galena, Moline, DeKalb & Rosemont
Our final day began in Galena, Illinois, a town that feels frozen in time. Its well-preserved 19th-century architecture, Ulysses S. Grant’s home, and a fun trolley tour gave us the story of this historically significant gem.

Next, we headed to Moline for a scenic ride aboard the Channel Cat Water Taxi, an affordable and peaceful way to explore the Quad Cities from the water. (Another great option is the Celebration Belle riverboat, offering themed cruises.)

Lunch at Johnny’s Italian Steakhouse was a throwback to Rat Pack-era glam with hearty, satisfying dishes. I feasted on a Monte Cristo.

Further along in DeKalb, we enjoyed a whiskey tasting at Whiskey Acres, Illinois’ first estate distillery and one of only two certified on-farm craft whiskey distilleries in the country.

Our final destination was Rosemont, just minutes from O’Hare International Airport and downtown Chicago. We stayed at the DoubleTree by Hilton Hotel Rosemont/Chicago O’Hare, a short distance to the Parkway Bank Park Entertainment District. This lively area is packed with restaurants, bars, and live music.

We dined at Crust Brewing Company, which had a killer menu and lively vibe—perfect for celebrating the end of our trip. Being the gambler that I am, I Ubered to Rivers Casino Des Plaines for a little slot play before bedtime.

If you have extra time in Rosemont, check out the Fashion Outlets of Chicago, with 130 designer and name-brand stores in a sleek, indoor setting.

Final Thoughts: Why You Should Explore Mississippi River Country
This whirlwind trip through Mississippi River Country was a perfect mix of city attractions, small-town charm, historic landmarks, and jaw-dropping scenery. Every stop introduced us to something new, from architectural wonders and delightful bakeries to river cruises and rolling farmland.

I loved watching the landscape change as we traveled—from bustling downtowns and lush river bluffs to hills and charming main streets. The people were welcoming, the food impressive, and the experiences diverse and enriching.

If you’re looking for a unique Midwest Road Trip, this Minnesota, Wisconsin, and Illinois route offers everything you could want—and a few surprises you wouldn’t expect.

Follow the Mississippi River and let it lead you to some of the Midwest’s most memorable moments.

For more about the Minnesota portion of this road trip, check out Melody’s article on what not to miss:
https://www.whereverimayroamblog.com/places-in-minnesota-you-cant-miss-mississippi-river-country-adventure/

Melody Pittman is the creative mind behind Wherever I May Roam Blog, an MSN-syndicated platform showcasing road trips, multi-generational travel, foodie adventures, cruising, and casino experiences. A seasoned influencer/freelancer, her work has appeared in Travel Awaits, Go RVing, Matador Network, The Local Palate, and Business Insider. She co-authored “100 Things to Do in West Virginia Before You Die,” showcasing her love for her home state. Melody’s passion for travel began in her teens and continues today as she uncovers hidden gems in small towns and local attractions. A National Park enthusiast and animal lover, she finds solace in road trips, off-the-radar destinations, and sunsets.  Melody co-hosts Southern Travelers Explore (#STE), a travel conference that unites travel writers and CVBs from across the U.S. She’s also a proud grandmother (“GB”) who loves multi-gen family vacations and embraces her role as part of the 50+ crowd thriving on social media. After a decade in Florida and a year of full-time RVing, she calls Mesquite, NV, home. Keep up with Melody’s adventures: https://www.whereverimayroamblog.com/

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