This three-day escape along the Mississippi’s Great River Road to Southeast Minnesota’s Bluff Country invites you to slow down and savor a rare landscape of river-carved valleys, limestone bluffs, and storybook towns. Unlike much of the state, this “Driftless Region” was untouched by flattening glaciers; instead, glacial melt carved an enchanting mosaic of layers and textures.Designed for those who crave nature, the itinerary blends gentle outdoor adventures like hiking, tubing, fishing, and biking with cozy cafés, local brews, and small-town charm. It celebrates mindful moments over miles logged, immersing travelers in the region’s spellbinding serenity.
Itinerary / 3 Days
PLAN YOUR TRIP
Sweeping views of the Mississippi River are a short hike away in Winona’s surrounding bluffs.
Courtesy of Explore Minnesota/Susie Loechler
Day 1Hike to Mississippi Views in Winona
Set out early to trace the Mississippi River south on a two-hour, 120-mile drive along the Great River Road, a National Scenic Byway that follows the iconic waterway from its Minnesota headwaters to the Gulf of Mexico. As the skyline slips away, the scenery opens like a pop-up book: the river widens, limestone bluffs rise from its banks, and timeless towns unfold along the way.
Your first stop is the historic and charming college town of Winona, where red brick facades line its storied streets. Break for coffee and breakfast at Blue Heron Coffeehouse, then hike the short trail up Sugar Loaf Bluff, the town’s craggy sentinel overlooking the panorama.
Continue 20 minutes south to Great River Bluffs State Park, immersing yourself deeper in the region’s dramatic outdoors. Combine the Kings Bluff and Great River Bluffs Trails into a four-mile lollipop-loop hike for sweeping Mississippi vistas, where oak-hickory woods nurture more than 100 species of birds.
Return to town for a front-row seat to the Mississippi over lunch at the Boat House—try the fish and chips with walleye, Minnesota’s state fish, or one of the chalkboard specials. On your way out, grab a sweet treat for the road from the century-old Bloedow Bakery, beloved for its freshly-fried, fluffy donuts, especially the maple Long John.
Shift inland 45 minutes (40 miles) to Lanesboro, where the intimate Root River greets you like an old friend. Regarded as the “Bed & Breakfast Capital of Minnesota,” the town is home to numerous Victorian-style bed-and-breakfasts. Green Gables Inn is known for its riverside garden grounds, and the Scandinavian Inn features a generous breakfast spread.
Top off your first day with dinner at Junipers, helmed by former Minneapolis fine-dining chef Tyler Shipton. Enjoy dishes like smash burgers and creamy mushroom bisque on the restaurant’s riverfront deck.
Your first stop is the historic and charming college town of Winona, where red brick facades line its storied streets. Break for coffee and breakfast at Blue Heron Coffeehouse, then hike the short trail up Sugar Loaf Bluff, the town’s craggy sentinel overlooking the panorama.
Continue 20 minutes south to Great River Bluffs State Park, immersing yourself deeper in the region’s dramatic outdoors. Combine the Kings Bluff and Great River Bluffs Trails into a four-mile lollipop-loop hike for sweeping Mississippi vistas, where oak-hickory woods nurture more than 100 species of birds.
Return to town for a front-row seat to the Mississippi over lunch at the Boat House—try the fish and chips with walleye, Minnesota’s state fish, or one of the chalkboard specials. On your way out, grab a sweet treat for the road from the century-old Bloedow Bakery, beloved for its freshly-fried, fluffy donuts, especially the maple Long John.
Shift inland 45 minutes (40 miles) to Lanesboro, where the intimate Root River greets you like an old friend. Regarded as the “Bed & Breakfast Capital of Minnesota,” the town is home to numerous Victorian-style bed-and-breakfasts. Green Gables Inn is known for its riverside garden grounds, and the Scandinavian Inn features a generous breakfast spread.
Top off your first day with dinner at Junipers, helmed by former Minneapolis fine-dining chef Tyler Shipton. Enjoy dishes like smash burgers and creamy mushroom bisque on the restaurant’s riverfront deck.
Historic brick storefronts set the stage for small-town life in Bluff Country’s downtown Lanesboro.
Courtesy of Explore Minnesota/Ryan Taylor
Day 2Tube, Kayak, or Canoe the Root River in Lanesboro
Today is all about the simple joy of being near the Root River—paddling on it and pedaling alongside it. Ease into your unhurried day with breakfast at your B&B or a local favorite like Paddle On Coffee & Maker Emporium.
Then, turn your attention to the water. The rivers here carved deep valleys in the landscape over millennia, untouched by the glaciers that flattened the rest of the state.
Rent tubes, kayaks, or canoes for a laid-back float or paddle with Root River Outfitters to explore these waterways, surrounded in some place by limestone bluffs up to 400 feet high. As you drift with the gentle current of the spring-fed Root River, look for eagles and deer as the dappled light dances across the water, casting a quiet spell. Regular shuttles between put-in and take-out spots let you go at your own pace with minimal wait.
Back on land, refuel with lunch at Pedal Pushers, which serves hearty, healthful dishes that showcase the best of local farms. Afterward, rent a bike from the charming Little River General Store and set out on the Root River Trail.
This paved, railbed-turned-recreational pathway meanders 42 miles, linking once-isolated towns and drawing new life to them. Your destination is the tiny hamlet of Whalan, population 63, just 4.6 miles away.
Wind through tunnels of hickory and oak, catching glimpses of open farmland and tree-topped bluffs between breaks in the canopy. Cross historic truss bridges with wooden railings, perfect for a pause to peer out at the river below. With each gentle turn, the soft whir of your wheels and the steady rhythm of the trail carry forward the morning’s magic.
In Whalan, reward yourself with a sought-after slice from Aroma Pie Shoppe, open seasonally Memorial Day through Labor Day. Run by a former roller derby skater who bakes upwards of 100 pies a day on weekends, the rotating selection spans seasonal flavors like the tangy strawberry-rhubarb and staples include favorites such as the silky banana cream and Midwestern sour cream raisin.
Then, turn your wheels back to Lanesboro for a late afternoon stroll of its arts-infused streets. Creativity weaves throughout daily life here—so much so that the entire town was declared an “arts campus.” Seek out its public art installations for smile-worthy surprises, including a restored 1950s phone booth that features recorded stories from locals.
End the day at Root River 102, where riverside views and a welcoming atmosphere make it the perfect spot to reflect on a day spent moving at the river’s pace.
Then, turn your attention to the water. The rivers here carved deep valleys in the landscape over millennia, untouched by the glaciers that flattened the rest of the state.
Rent tubes, kayaks, or canoes for a laid-back float or paddle with Root River Outfitters to explore these waterways, surrounded in some place by limestone bluffs up to 400 feet high. As you drift with the gentle current of the spring-fed Root River, look for eagles and deer as the dappled light dances across the water, casting a quiet spell. Regular shuttles between put-in and take-out spots let you go at your own pace with minimal wait.
Back on land, refuel with lunch at Pedal Pushers, which serves hearty, healthful dishes that showcase the best of local farms. Afterward, rent a bike from the charming Little River General Store and set out on the Root River Trail.
This paved, railbed-turned-recreational pathway meanders 42 miles, linking once-isolated towns and drawing new life to them. Your destination is the tiny hamlet of Whalan, population 63, just 4.6 miles away.
Wind through tunnels of hickory and oak, catching glimpses of open farmland and tree-topped bluffs between breaks in the canopy. Cross historic truss bridges with wooden railings, perfect for a pause to peer out at the river below. With each gentle turn, the soft whir of your wheels and the steady rhythm of the trail carry forward the morning’s magic.
In Whalan, reward yourself with a sought-after slice from Aroma Pie Shoppe, open seasonally Memorial Day through Labor Day. Run by a former roller derby skater who bakes upwards of 100 pies a day on weekends, the rotating selection spans seasonal flavors like the tangy strawberry-rhubarb and staples include favorites such as the silky banana cream and Midwestern sour cream raisin.
Then, turn your wheels back to Lanesboro for a late afternoon stroll of its arts-infused streets. Creativity weaves throughout daily life here—so much so that the entire town was declared an “arts campus.” Seek out its public art installations for smile-worthy surprises, including a restored 1950s phone booth that features recorded stories from locals.
End the day at Root River 102, where riverside views and a welcoming atmosphere make it the perfect spot to reflect on a day spent moving at the river’s pace.
Go fly-fishing in the spring-fed waters of the Root River near Spring Valley, MN.
Courtesy of Explore Minnesota/Ryan Taylor
Day 3Fly Fish or Tour the Mystery Cave in Forestville
Wake up to your final B&B breakfast spread or try Lanesboro Pastry Shoppe before a detour-filled route back to the Twin Cities of Minneapolis-St. Paul. Your first stop, 35 minutes (26 miles) away, is Forestville / Mystery Cave State Park, where the region’s karst terrain of spring-fed streams, sinkholes, and hidden caves reveals new layers of wonder in the landscape.
After a day spent floating on and biking along the Root River and its branches, today invites you to step into its calm flow or explore the enchanting world carved by its underground disappearing springs.
For fly fishing, hire a guide from a local outfitter like Lanesboro’s Root River Rod Co. and follow them to one of the park’s crystal-clear creeks teeming with wild brown trout. Wade through its cool currents, meditating on each cast as the stream’s babbling draws you further into the present moment.
For a subterranean adventure, descend into the depths of Mystery Cave. It’s Minnesota’s longest cave with 13 miles of maze-like passages and one of the few fully accessible caves in the U.S. The cool 48-degree air immediately envelops you as you slip into this otherworldly realm where nature’s artistry surprises around every turn—dripping stalactites hang like chandeliers, undulating walls shimmer, jewel-toned pools mesmerize, and trickling streams whisper secrets of centuries past.
Reemerge onto the open road, passing through rolling bluffs, farmland, and winding waterways on your way to Squash Blossom Farm, one hour (45 miles) away. This local “pizza farm” harvests ingredients steps from its wood-fired ovens, making each pizza a celebration of fresh, farm-to-table flavors. With live music, open-air seating, and verdant farmstead views, it’s the perfect place to linger, savor the season’s bounty, and toast to your escape—a final piece in your mosaic of experiences in Southeast Minnesota.
After a day spent floating on and biking along the Root River and its branches, today invites you to step into its calm flow or explore the enchanting world carved by its underground disappearing springs.
For fly fishing, hire a guide from a local outfitter like Lanesboro’s Root River Rod Co. and follow them to one of the park’s crystal-clear creeks teeming with wild brown trout. Wade through its cool currents, meditating on each cast as the stream’s babbling draws you further into the present moment.
For a subterranean adventure, descend into the depths of Mystery Cave. It’s Minnesota’s longest cave with 13 miles of maze-like passages and one of the few fully accessible caves in the U.S. The cool 48-degree air immediately envelops you as you slip into this otherworldly realm where nature’s artistry surprises around every turn—dripping stalactites hang like chandeliers, undulating walls shimmer, jewel-toned pools mesmerize, and trickling streams whisper secrets of centuries past.
Reemerge onto the open road, passing through rolling bluffs, farmland, and winding waterways on your way to Squash Blossom Farm, one hour (45 miles) away. This local “pizza farm” harvests ingredients steps from its wood-fired ovens, making each pizza a celebration of fresh, farm-to-table flavors. With live music, open-air seating, and verdant farmstead views, it’s the perfect place to linger, savor the season’s bounty, and toast to your escape—a final piece in your mosaic of experiences in Southeast Minnesota.