Things to Do in Minnesota's Bluff Country

Okay, first things first: yes, this is the town Winona Ryder is named for. No, she did not grow up there (her mother went into labor while visiting family there, hence her name). Celebrity connections aside, Winona, a college town positioned on the banks of the Mississippi River near the Wisconsin border, has big, artsy bona fides.

The town is home to the Great River Shakespeare Festival, the state's largest professional celebration of the Bard, which performs at the Historic Masonic Center, a recently renovated theater seating an intimate 250 patrons.

There’s also unmissable visual art: the Minnesota Marine Art Museum, a striking, riverfront cedar-shingled building surrounded by peninsulas of goldenrod and deep purple irises, is the sort of museum that belies the size of the town it’s in (think the Palm Springs Art Museum or Ordrupgaard in Denmark). With six beautiful galleries, the water-focused museum has recently hosted exhibitions featuring artists like Erik Jon Olson, Mustafah Abdulaziz, and Kristian Brevik. 

Peckish? The museum’s café serves Minnesota classics like walleye and wild rice, and its scenic patio is open during the summer months.

In 2027, Winona will gain a world-class music performance venue and art gallery, Masterpiece Hall. Currently under construction, Masterpiece Hall will play host to the city’s already nationally regarded Beethoven Festival (2025’s special guest was violinist/conductor Joshua Bell), while the gallery will feature works from serious heavyweights like Pablo Picasso and Henri Matisse.

Winona also has abundant natural beauty. Sugar Loaf Bluff, a rock pinnacle that stands 500 feet above Lake Winona, was created from the quarrying of the bluff’s limestone cap layer. Today, it serves as a hewn exclamation point, drawing your eye from almost anywhere in town. The perfect place for hiking year-round, Winona is also home to a renowned Ice Climbing Park (yes, ice climbing, like rock climbing on ice) and the popular Winona Ice Fest.

Then, of course, there’s Bloedow’s. The bakery’s famed donuts are “well nigh perfect,” according to Saveur magazine. Experts recommend ordering online before you show up, lest you miss out on the last maple long john, and timing your visit to a Thursday (if you can), when the filled donut special is Bavarian cream.

See more things to do in Winona.

Red Wing is synonymous with heritage wear, thanks to the presence of Red Wing Shoes, which GQ declared “legendary American-made shoes...impervious to wherever the trend cycle heads next.”

Founded in 1905, Red Wing Shoes are as in-demand and status-y as they are practical. Visit the flagship store, and you’ll be greeted by a 20-foot boot (the world’s largest), a small museum, and yes, a basement full of discounted products. It may be your only chance to buy a pair for less, so don’t hold back.

But don’t make it your only stop in Red Wing — this charming river town is chock-full of antique shops, many of which stock vintage Red Wing Stoneware and Pottery. Distinctive, wing-emblazoned crocks and jugs are their most famous products, but you can also find dinnerware and decorative pieces.

Discover the history of iconic salt glazing at the Pottery Museum of Red Wing, then head to Pottery Place Antiques to hunt for a souvenir.

A culture of craft runs deep in Red Wing. You can shop gifts from local artists and makers at the Red Wing Arts Gift Shop or the latest Smith + Trade Mercantile location, then get a custom piece at DeLeon Jewelers.

Looking for a traditional folk lever harp? You’re in luck! Stoney End has been handcrafting affordable folk instruments for nearly 40 years, including harps, dulcimers, and banjos.

Adourn carries curated home goods and refreshed vintage pieces. Fair Trade Books also has Persian rugs for sale; Heimie’s Haberdashery is a must-stop for sophisticated menswear; and a short drive down County Road 1 will bring you to Featherstone Pottery, where brothers Tom and Jeff Larkin craft heirloom-quality ceramics on their family farm.

As if that weren’t enough small-town charm, Red Wing operates a seasonal hop-on, hop-off trolley, so you can live out your Judy Garland fantasy while you take in views of the river.

Looking to spend the night? The historic St. James Hotel (owned by Red Wing boots and a member of Historic Hotels of America) is a bucket-list stay for any visitor, with beautifully maintained rooms that will make you feel like a special guest star in an episode of “The Gilded Age.” The St. James also has its own Prohibition-style cocktail lounge, The Port, with an antique bar sourced from an actual 1860s speakeasy.

The Moondance Inn, a bed-and-breakfast set in a renovated 1874 mansion, is the platonic ideal of a romantic getaway, with two-person whirlpool tubs, fireplaces, and richly appointed four-poster beds. For more of a relaxing rural vibe, book Round Barn Farm, a five-room B&B that offers bucolic countryside views and a historic gazebo, where you can post up for hours with a good book and (complimentary) beverage.

Looking for an easy add-on to a trip to Minneapolis? Both Red Wing and Winona are stops on Amtrak’s Borealis line and feature walkable, shoppable downtowns, making them perfect weekend getaways or day trips from the cities. 

Tickets start around $10 (depending on date and time). It takes under an hour to get to Red Wing, and about 90 minutes to reach Winona. But the ride is an adventure in itself, with views of the Mississippi River that charm in every season, from the confetti rush of fall color to the snow-covered magic of winter.

Every year, over a million people travel to the Mayo Clinic from every corner of the globe. There’s no mystery as to why: Mayo is commonly considered (and ranked) the best hospital in the entire world. 

Many famous patients have walked through the art-filled foyer over the years, but the hospital isn’t an exclusive celebrity enclave. It’s a destination medical center on the cutting edge of research and technology, employing 7,300 physicians and scientists and 66,000 healthcare workers and staff. 

That also makes it the economic hub of Rochester, the largest city in Bluff Country.

Rochester is located on the Zumbro River, a tributary of the Mississippi, and has a vibrant, cosmopolitan feel that belies its relatively small geographic footprint. Visitors can take a trolley tour through the historic Pill Hill District, a collection of 130 historic homes on a limestone bluff, including the Dr. William J. Mayo House.

Culture-seekers will want to plan a visit to legendary bronze sculptor Charles E. Gagnon’s former home, which is now an open studio and sculpture garden, while outdoorsy types should pencil time to see Quarry Hill Nature Center, a 329-acre park that features a limestone fossil quarry, miles of biking and hiking trails, and a restored oak savanna.

In winter, downtown Rochester transforms for Social-ICE, an all-out celebration of winter that lights up the streets with a dizzying array of ice bars. You can, of course, do your drinking indoors at breweries like Forager and Little Thistle, or make a reservation at one of the city’s outstanding restaurants. 

We love Marrow, an understated bistro in a historic building that serves boundary-pushing dishes like grilled eel with braised daikon and celery root chowder, and barbecued carrots served with a swoosh of black lime labneh and festooned with pistachio dukkah. Another local favorite is ThaiPop, a plant-filled escape where you can tuck into a perfectly balanced khao soi curry or try Minnesota’s state fish (walleye) in a signature three-flavor sauce topped with crispy garlic and served alongside a steaming bowl of jasmine rice.

Plan a visit to the Mayo Clinic and find out where to stay, what to eat, and all our favorite things to do.

The Root River Trail is a 42-mile paved bike route that takes you straight through the heart of Bluff Country. Constructed on a former railroad line, the trail is mostly flat (the big hills stay above your head) and passes through some of Bluff Country’s cutest small towns, including Harmony, Preston, and Whalan. 

Not to mention Aroma Pie Shop, a seasonal Whalan staple for fresh-baked, from-scratch pies that draws hordes of hungry bikers each spring through fall. Our favorite is the blueberry-rhubarb, which swaps rich, slightly tannic blueberries for rhubarb’s usual bedfellow.

Also on the Root River Trail is Lanesboro, the Bed and Breakfast Capital of Minnesota, where you can toss a pebble and hit a B&B so eye-poppingly charming you’ll think you’ve teleported to Stars Hollow. Oakenwald Terrace, the Scandinavian Inn, Berwood Hill, and Scanlan House are just a handful of the historic Lanesboro properties that have been converted into quaint, boutique accommodations. 

While you’re there, catch a show at Commonweal Theatre, grab a meal at the cheekily named Pedal Pushers Café, put back a few brews at Sylvan (located in a former wood-stacked granary), and cap off your visit with a sweet treat from Another Time Ice Cream Parlour.

After you’ve rested sufficiently, bike on down to La Crescent, home of the USA Cycling Gravel National Championships. There, you can toast to your journey at River View Winery while gazing at the mighty Mississippi. 

Cheers to you!

Check out a complete rundown of Minnesota's best B&Bs.

Bluff Country is home to not one, but two breath-stealing caves. Mystery Cave, located in Forestville/Mystery Cave State Park, is the longest cave in Minnesota. With 13 miles of naturally formed passages, it has multiple seasonal tour options, including a scenic tour that takes you to an underground turquoise lake and a rugged tour lit only by lanterns.

Want to cosplay as a mid-century spelunker? Mystery Cave also offers a four-hour wild caving tour that includes, we quote, “climbing, crawling, stooping and sliding.” 

Okay, then! Be sure to grab your boots and leave your claustrophobic friend at home!

In Harmony, you'll find Niagara Cave, named a USA Today 10 Best, and perhaps the only place in the nation where you can find a subterranean wedding chapel. Guided tours offered May–October will take you through dramatic, stream-sculpted passageways, an underground waterfall, and fossils dating back 450 million years.

See more caves in Minnesota.

Ever heard of a little thing called water skiing? Did you know it was invented in Lake City, a town located on the shores of Lake Pepin, which is also the widest portion of the Mississippi River? The city is rightfully proud of this legacy, and each summer the town hosts Water Ski Days, a festival that honors one of the most unabashedly chaotic and plain-old-fun elements of lake life.

If you’ve never been water skiing, Lake City is the perfect place to try it — or you can just get out on the water for a regular old boat ride. Charter a sailboat! Rent a kayak! Enjoy the feeling of absolute freedom inherent to floating along the most historically significant body of water in American history!

Lake City is also close to Frontenac State Park, one of the best places in the country to catch a view of a bald eagle and see fall colors.

See all our favorite things to do in Lake City.

Outdoor Life magazine named the multi-state driftless region, which includes Minnesota’s Bluff Country, as “The Best Kept Secret in the Trout World,” going on to say that “it’s an ideal landscape for supporting trout, and with that comes a long and strong trout fishing heritage.”

In fact, there are over 700 miles of trout-fishing streams in Bluff Country, and anglers can catch brook, brown, and rainbow trout. Trout fishing culture is so strong here that in 2012, the Minnesota Trout Association unveiled a self-guided nine-hole trout fishing course along the Root River in Preston.

And if you’re wondering what’s for dinner, it’s trout. And if you wait until breakfast, we’re having trout.

Find out more about fishing in Minnesota.

There’s a very good reason the National Eagle Center is in Wabasha, Minnesota. It’s located on a geographic anomaly at the confluence of the Chippewa and Mississippi rivers, where ice rarely forms, making it the perfect fishing ground for migrating bald eagles. 

Believe it or not, this iconic bird wasn’t the country’s official avian mascot until recently — and much of the efforts were thanks to the National Eagle Center and their close partners from the Prairie Island Indian Community.

Four non-releasable eagle ambassadors (and one red-tailed hawk!) call the National Eagle Center home. Visitors can hang out with the center’s eagles face-to-face, as well as see them soar from a riverfront amphitheater. Educational exhibitions include a replica eagle nest and a motion-capture flight simulation that turns you into the eagle!

Depending on the time of year you visit, you can also book a special experience, including field trips to observe nesting season, a guided river cruise, and a special two-and-a-half-hour habitat tour focused on bald eagles or the elusive golden eagle, depending on the season.

Looking for somewhere to stay? The Anderson House Hotel is the oldest historic hotel in the state, operational since 1856. The rooms feature hand-carved bed frames and patterned wallpaper, and a game room on the main floor has foosball, ping-pong, and a variety of board games — just in case you need to hype up your crew after a day of big birdwatching.

For couples, we love Turning Waters Bed and Breakfast, and don’t forget to pop over to the B&B’s garage, which has been converted into Hoppy Girl Brewing.

The most distinctive feature of Bluff Country is, of course, the titular bluffs. From Sugar Loaf in Winona to Sorin’s Bluff in Red Wing, this region is full of dramatic peaks set above the Mississippi River Valley, which means the views are abundant.

We love hiking Memorial Park, Frontenac, He Mni Can-Barn Bluff, Great River Bluffs State Park, and, of course, Sugar Loaf, where the brave among us can find some of the state’s most iconic rock climbing.

There is nothing better than seeing a panoramic view at any time of year, but Bluff Country is especially becoming in fall, when the sugar maples, basswoods, and red oaks are lit in crimson, umber, and goldenrod.

See our favorite places to go hiking in Bluff Country.

Many parents have ideas about limiting screen time and letting their children play only with handmade wooden toys. But where does one actually get handmade wooden toys? 

Good news, parents: LARK has you covered. They’ve been making beautifully handcrafted toys for over 30 years, from pullable penguins to puzzles. There’s even a happy paddler for aspiring Boundary Waters adventurers.

But that’s not all. LARK Toys has an extensive, hand-picked selection of toys and games from other makers, a bookstore, a toy museum, a café, and even a carousel with hand-carved animals ready for riding.

At LARK Toys, we're all forever young.