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This Enchanting Road Trip Will Take You To 12 Of Minnesota’s Most Charming Towns


Forget the Mall of America—Minnesota’s real treasures are hiding in plain sight!

Let’s embark on a whirlwind tour of twelve towns that’ll make you wonder why you ever wasted time in a megamall.

1. Lanesboro

Lanesboro: Where the bikes outnumber the cars and the scenery rivals a Bob Ross painting. Happy little trees everywhere!Lanesboro: Where the bikes outnumber the cars and the scenery rivals a Bob Ross painting. Happy little trees everywhere!
Lanesboro: Where the bikes outnumber the cars and the scenery rivals a Bob Ross painting. Happy little trees everywhere! Photo Credit: Wikipedia

Nestled in the heart of Minnesota’s Bluff Country, Lanesboro is like stepping into a Norman Rockwell painting—if Norman Rockwell had a thing for bike trails and bed & breakfasts.

This quaint town, with its lovingly preserved 19th-century storefronts, is a haven for those who think “rush hour” means more than three people at the local coffee shop.

The Root River State Trail runs right through town, offering 42 miles of scenic biking.

And by “scenic,” I mean you’ll be so distracted by the views that you might forget to pedal.

Brick beauties line the street, looking like they've stepped right out of a historical romance novel. Mr. Darcy, is that you?Brick beauties line the street, looking like they've stepped right out of a historical romance novel. Mr. Darcy, is that you?
Brick beauties line the street, looking like they’ve stepped right out of a historical romance novel. Mr. Darcy, is that you? Photo Credit: John Roever

Don’t worry, though—the trail is mostly flat, perfect for those of us whose idea of exercise is reaching for the TV remote.

For a taste of local culture (and I mean that literally), stop by the Lanesboro Local Marketplace.

It’s a cornucopia of regional goodies that’ll make you want to move here just for the farmers’ market.

And if you’re feeling particularly adventurous, try the lutefisk.

It’s a Scandinavian delicacy that’s… well, let’s just say it’s an acquired taste.

Think of it as Minnesota’s version of a culinary extreme sport.

2. Park Rapids

Park Rapids: Where Main Street is wider than your grandma's stories and twice as charming. Norman Rockwell would've had a field day here!Park Rapids: Where Main Street is wider than your grandma's stories and twice as charming. Norman Rockwell would've had a field day here!
Park Rapids: Where Main Street is wider than your grandma’s stories and twice as charming. Norman Rockwell would’ve had a field day here! Photo Credit: Jasperdo

If you’ve ever wondered where all those “10,000 lakes” in Minnesota are hiding, Park Rapids is a good place to start looking.

This charming town is the gateway to Itasca State Park, home to the headwaters of the Mississippi River.

Yes, that Mississippi River.

It starts here as a humble stream you could practically hop over.

Talk about humble beginnings!

Trading Post treasures await! It's like your attic and a time machine had a baby, right on Main Street.Trading Post treasures await! It's like your attic and a time machine had a baby, right on Main Street.
Trading Post treasures await! It’s like your attic and a time machine had a baby, right on Main Street. Photo Credit: Wikipedia

Main Street in Park Rapids is wider than a football field, which is great news for those of us who struggle with parallel parking.

Legend has it that the street was designed this wide so horse-drawn wagons could make U-turns.

These days, it’s mostly used for leisurely strolls and the occasional impromptu game of street hockey.

For a true taste of Minnesota nice (and some pretty nice taste), head to Necce’s Ristorante.

It’s an Italian joint in the heart of lake country, proving that good pasta knows no geographical bounds.

Just don’t ask for lutefisk on your spaghetti—that’s a fusion cuisine bridge too far.

3. Stillwater

Stillwater's Main Street: A colorful tapestry of shops that'll make you wonder if you've stumbled into a Wes Anderson film set.Stillwater's Main Street: A colorful tapestry of shops that'll make you wonder if you've stumbled into a Wes Anderson film set.
Stillwater’s Main Street: A colorful tapestry of shops that’ll make you wonder if you’ve stumbled into a Wes Anderson film set. Photo credit: Justine Canlas

Perched on the banks of the St. Croix River, Stillwater is to charming river towns what Swiss cheese is to holes—it’s got it in spades.

Known as the “Birthplace of Minnesota,” Stillwater has more history than your grandpa has stories about “the good old days.”

The town is famous for its antique shops, which is great news for anyone who’s ever thought, “You know what my house needs? More stuff from other people’s attics.”

But seriously, these shops are treasure troves of the weird and wonderful.

Where else can you find a vintage butter churn next to a lava lamp?

The St. Croix River lazily meanders by, as if it too is window shopping along Stillwater's picturesque waterfront.The St. Croix River lazily meanders by, as if it too is window shopping along Stillwater's picturesque waterfront.
The St. Croix River lazily meanders by, as if it too is window shopping along Stillwater’s picturesque waterfront. Photo credit: Eiwor Forsberg

For a truly unique experience, take a ride on the Stillwater Lift Bridge.

It’s like a seesaw for cars, except you don’t need to find a buddy of equal weight to make it work.

And if you’re feeling particularly brave (or just really like heights), you can walk across it.

Just don’t look down—unless you want to see some really big fish.

4. Red Wing

Red Wing: Where the buildings are as sturdy as their famous boots. This town's got sole, and it shows!Red Wing: Where the buildings are as sturdy as their famous boots. This town's got sole, and it shows!
Red Wing: Where the buildings are as sturdy as their famous boots. This town’s got sole, and it shows! Photo credit: Visitors Center

Red Wing is proof that a town can be famous for both its scenery and its footwear.

Home to the iconic Red Wing Shoes, this Mississippi River town has been keeping feet happy and blister-free since 1905.

They even have the world’s largest boot on display—it’s a size 638½ D.

That’s not a typo, folks.

It’s big enough to house a small family or serve as an emergency shelter during a Minnesota winter.

The mighty Mississippi meets small-town charm. It's like Mark Twain's daydreams came to life, minus the whitewashing.The mighty Mississippi meets small-town charm. It's like Mark Twain's daydreams came to life, minus the whitewashing.
The mighty Mississippi meets small-town charm. It’s like Mark Twain’s daydreams came to life, minus the whitewashing. Photo credit: Visitors Center

But Red Wing isn’t just about oversized footwear.

The town is nestled among the bluffs of the Mississippi, offering views that’ll make your Instagram followers green with envy.

Hike up to Barn Bluff for a panorama that’ll have you questioning why you ever thought flat land was interesting.

For a taste of local flavor, swing by the Red Wing Brewery.

They’ve resurrected pre-prohibition beer recipes, so you can drink like it’s 1919.

Just remember, what happens in Red Wing, stays in Red Wing—unless you post it on social media, in which case it stays on the internet forever.

5. Grand Marais

Grand Marais: Where Lake Superior laps at your feet and the air smells of adventure (and maybe a little fish).Grand Marais: Where Lake Superior laps at your feet and the air smells of adventure (and maybe a little fish).
Grand Marais: Where Lake Superior laps at your feet and the air smells of adventure (and maybe a little fish). Photo credit: Chad Rawson

Tucked away on the North Shore of Lake Superior, Grand Marais is the kind of town that makes you want to quit your job, buy a kayak, and spend the rest of your days paddling into the sunset.

It’s been voted “America’s Coolest Small Town,” which is quite an achievement considering Minnesota’s reputation for, well, coolness.

The town is an artist’s paradise, with more galleries per capita than coffee shops in Seattle.

And that’s saying something.

Whether you’re into painting, pottery, or interpretive dance inspired by the flight patterns of seagulls, Grand Marais has got you covered.

Colorful buildings dot the shoreline like a box of crayons spilled by a giant. Paul Bunyan, was that you?Colorful buildings dot the shoreline like a box of crayons spilled by a giant. Paul Bunyan, was that you?
Colorful buildings dot the shoreline like a box of crayons spilled by a giant. Paul Bunyan, was that you? Photo credit: Gav

For a truly “grand” experience, head to the Grand Marais Harbor.

Watch the fishing boats come in with the day’s catch, or try your hand at skipping stones.

Pro tip: the flatter the stone, the better.

If your stone looks like a potato, you might want to consider eating it instead of throwing it.

6. Winona

Winona: Where the Mississippi Valley views are so stunning, even the eagles stop to take selfies.Winona: Where the Mississippi Valley views are so stunning, even the eagles stop to take selfies.
Winona: Where the Mississippi Valley views are so stunning, even the eagles stop to take selfies. Photo credit: Karl “Zero” Olsen

Nestled between bluffs and the Mississippi River, Winona is an island city that’s as rich in culture as it is in scenery.

It’s mentioned in Bob Dylan’s “The Wall Breaker,” but don’t worry—you don’t need to be a folk music aficionado to appreciate its charms.

Winona is home to the Minnesota Marine Art Museum, which sounds like it should be full of stuffed fish but is actually a world-class collection of art inspired by water.

Related: This Stunning State Park in Minnesota is Like Stepping into an Andrew Wyeth Painting

Related: This 282-Acre Wonder at Minnesota’s Pipestone National Monument is a Labyrinth of Rock Formations to Explore

Related: Discover Itasca State Park, the Best State Park in Minnesota for an Unforgettable Day Out

It’s like someone took the Louvre, dunked it in the Mississippi, and plopped it down in Minnesota.

Who knew water could inspire so much more than just the need for a bathroom break?

Main Street Winona: More charm per square foot than a leprechaun convention. And probably better beer, too!Main Street Winona: More charm per square foot than a leprechaun convention. And probably better beer, too!
Main Street Winona: More charm per square foot than a leprechaun convention. And probably better beer, too! Photo credit: Winona State University

For a truly unique experience, visit during the Frozen River Film Festival.

It’s like Sundance, but with more parkas and hot cocoa.

And if you’re lucky, you might catch a film about the mating habits of walleye.

Now that’s entertainment you can’t get in Hollywood!

7. Northfield

Northfield: Where the buildings are older than your dad's jokes, but infinitely more appealing.Northfield: Where the buildings are older than your dad's jokes, but infinitely more appealing.
Northfield: Where the buildings are older than your dad’s jokes, but infinitely more appealing. Photo credit: Wikipedia

Northfield’s motto is “Cows, Colleges, and Contentment,” which sounds like the world’s most relaxed episode of Jeopardy.

This charming town is home to not one, but two prestigious colleges: St. Olaf and Carleton.

It’s like Cambridge, but with more cornfields and fewer British accents.

The town is famous for thwarting a bank robbery by the Jesse James gang in 1876.

Division Street: So quaint and inviting, you'll half expect to see Jimmy Stewart running down it yelling about angels and bells.Division Street: So quaint and inviting, you'll half expect to see Jimmy Stewart running down it yelling about angels and bells.
Division Street: So quaint and inviting, you’ll half expect to see Jimmy Stewart running down it yelling about angels and bells. Photo credit: Jonathan Hernandez

They celebrate this every year with the Defeat of Jesse James Days, which includes a reenactment of the failed robbery.

It’s like a Western movie come to life, except the good guys win and nobody actually gets shot.

For a taste of local culture (and some pretty great scones), head to The Hideaway Coffeehouse and Winebar.

It’s a coffee shop by day and a wine bar by night, proving that Northfield knows how to cater to both the caffeinated and the… well, differently caffeinated.

8. Wabasha

Wabasha: Where the eagles soar and the Mississippi flows, it's like nature's own IMAX theater.Wabasha: Where the eagles soar and the Mississippi flows, it's like nature's own IMAX theater.
Wabasha: Where the eagles soar and the Mississippi flows, it’s like nature’s own IMAX theater. Photo credit: Wikipedia

Perched on the banks of the Mississippi, Wabasha is famous for two things: its bald eagles and being the filming location for “Grumpy Old Men.”

It’s like a retirement home for national symbols and Hollywood stars, except the eagles are real and Jack Lemmon isn’t actually ice fishing anymore.

The National Eagle Center is a must-visit.

It’s like a spa day for bird watchers, except instead of cucumber slices on your eyes, you get to see majestic bald eagles up close.

Just remember: no matter how patriotic you’re feeling, these birds are not for petting.

Main Street Wabasha: So picturesque, you'll swear you've wandered onto a movie set. Jack Lemmon and Walter Matthau not included.Main Street Wabasha: So picturesque, you'll swear you've wandered onto a movie set. Jack Lemmon and Walter Matthau not included.
Main Street Wabasha: So picturesque, you’ll swear you’ve wandered onto a movie set. Jack Lemmon and Walter Matthau not included. Photo credit: Enter

For a taste of local flavor, stop by Slippery’s Tavern, featured in “Grumpy Old Men.”

Order the walleye and pretend you’re in the movie.

Just don’t start any feuds with the locals over fishing spots or romantic interests.

That rarely ends well, even in Hollywood.

9. New Ulm

New Ulm: Where the hills are alive with the sound of… polka? It's like The Sound of Music met Oktoberfest.New Ulm: Where the hills are alive with the sound of… polka? It's like The Sound of Music met Oktoberfest.
New Ulm: Where the hills are alive with the sound of… polka? It’s like The Sound of Music met Oktoberfest. Photo credit: Wikipedia

New Ulm is so German, you half expect to see lederhosen-clad folks yodeling down the street.

This town takes its heritage seriously—they even have a 45-foot-tall glockenspiel.

It’s like a giant cuckoo clock, except instead of a bird, you get to see figurines of the town’s settlers.

It’s history meets Disneyland, minus the overpriced mouse ears.

Downtown New Ulm: More German charm than a lederhosen fashion show. Grab a pretzel and enjoy the view!Downtown New Ulm: More German charm than a lederhosen fashion show. Grab a pretzel and enjoy the view!
Downtown New Ulm: More German charm than a lederhosen fashion show. Grab a pretzel and enjoy the view! Photo credit: Minnesota River Valley National Scenic Byway

The Hermann Monument, a 102-foot-tall copper statue, stands guard over the town.

It’s like the Statue of Liberty’s distant cousin who decided the Midwest was more his speed.

Climb to the top for views that’ll make you say “Wunderbar!” even if you don’t speak a lick of German.

For a true taste of New Ulm, visit Schell’s Brewery, the second-oldest family-owned brewery in America.

Take a tour, sample some brews, and toast to the fact that you’re drinking beer in a town that takes Oktoberfest very, very seriously.

Prost!

10. Ely

Ely: Where the wilderness meets small-town charm. It's like Grizzly Adams opened a boutique hotel.Ely: Where the wilderness meets small-town charm. It's like Grizzly Adams opened a boutique hotel.
Ely: Where the wilderness meets small-town charm. It’s like Grizzly Adams opened a boutique hotel. Photo credit: Wikipedia

Ely is the gateway to the Boundary Waters Canoe Area Wilderness, which is a fancy way of saying it’s where people go when they want to pretend they’re living in the 1800s, but with Gore-Tex jackets and bear-proof food canisters.

This town is so in tune with nature, they have not one, but two wildlife centers: the International Wolf Center and the North American Bear Center.

It’s like a zoo, except the animals are in their natural habitat and you’re the one in the cage (aka your car).

The gateway to the Boundary Waters, where adventure lurks around every corner. Bigfoot sightings not guaranteed, but highly encouraged.The gateway to the Boundary Waters, where adventure lurks around every corner. Bigfoot sightings not guaranteed, but highly encouraged.
The gateway to the Boundary Waters, where adventure lurks around every corner. Bigfoot sightings not guaranteed, but highly encouraged. Photo credit: MPR News

For a true taste of the north woods, stop by the Ely Steak House.

Order the Bucky Burger, a local legend that’s big enough to feed a small wolf pack.

Just don’t try to howl with your mouth full—that’s considered poor form, even in Ely.

11. Taylors Falls

Taylors Falls: Where the St. Croix River carved out a masterpiece. Mother Nature's own sculpture garden!Taylors Falls: Where the St. Croix River carved out a masterpiece. Mother Nature's own sculpture garden!
Taylors Falls: Where the St. Croix River carved out a masterpiece. Mother Nature’s own sculpture garden! Photo credit: Explore Minnesota

Taylors Falls is proof that sometimes, Mother Nature likes to show off.

The town is home to Interstate State Park, where the St. Croix River carved out a gorge that’s like the Grand Canyon’s smaller, greener cousin.

It’s the kind of place that makes geologists weep with joy and the rest of us scramble for our cameras.

Take a scenic boat tour of the St. Croix River.

It’s like a history lesson and a nature documentary rolled into one, minus the stuffy classroom and David Attenborough’s voice-over.

The river view's so good, you'll forget you're not in a Bob Ross painting. Just don't try to add any happy little trees.The river view's so good, you'll forget you're not in a Bob Ross painting. Just don't try to add any happy little trees.
The river view’s so good, you’ll forget you’re not in a Bob Ross painting. Just don’t try to add any happy little trees. Photo credit: Minnesota Prairie Roots

Keep an eye out for rock formations with names like “The Old Man of the Dalles.”

It’s like cloud-watching, but with less chance of neck strain.

For a taste of local flavor, stop by the Drive-In Restaurant.

It’s a blast from the past, serving up burgers and malts since 1956.

Order a Pineapple Boat—it’s a hollowed-out pineapple filled with soft serve.

Nothing says “I’m on vacation” like eating ice cream out of a tropical fruit.

12. Pipestone

Pipestone: Where the prairie meets history. It's like stepping into a living, breathing museum, minus the "Do Not Touch" signs.Pipestone: Where the prairie meets history. It's like stepping into a living, breathing museum, minus the "Do Not Touch" signs.
Pipestone: Where the prairie meets history. It’s like stepping into a living, breathing museum, minus the “Do Not Touch” signs. Photo credit: Traveling with Tom

Pipestone is named after the red stone quarried here for centuries by Native Americans to make sacred pipes.

It’s like a geologist’s candy store, except you can’t eat the rocks (please don’t try).

Visit Pipestone National Monument to see Native American craftsmen demonstrating traditional pipe-making techniques.

It’s like watching history come alive, minus the uncomfortable period costumes and cheesy reenactments.

Main Street Pipestone: More character than a Dickens novel, with a dash of Wild West thrown in for good measure.Main Street Pipestone: More character than a Dickens novel, with a dash of Wild West thrown in for good measure.
Main Street Pipestone: More character than a Dickens novel, with a dash of Wild West thrown in for good measure. Photo credit: Wikimedia Commons

For a quirky photo op, check out the “Ghost of the Calumet Inn.”

It’s a life-sized metal sculpture of a ghost that appears to be walking through a wall.

It’s either a clever piece of art or proof that even spirits need a good night’s sleep at a cozy inn.

There you have it, folks—twelve towns that prove Minnesota is more than just lakes and “you betcha”s.

From German glockenspiels to ghostly inns, these charming spots are waiting to steal your heart faster than you can say “uff da.”

Plot your path to adventure!

This map is your key to smooth travels and exciting discoveries.

enchanting minnesota road trip mapenchanting minnesota road trip map

So gas up the car, pack your sense of adventure (and maybe some mosquito repellent), and hit the road.

Minnesota nice isn’t just a saying—it’s a destination!





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