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This Jazz Age Road Trip In Wisconsin Will Take You To 10 Historic Homes Inspired By The Great Gatsby


What if you could explore the timeless elegance of the Jazz Age without leaving Wisconsin?

This carefully curated road trip showcases ten historic homes that perfectly embody the charm and allure of the 1920s.

1. Villa Terrace Decorative Arts Museum (Milwaukee)

Gardens cascading like a green waterfall – it's Wisconsin's answer to the Hanging Gardens of Babylon, minus the ancient mystery.Gardens cascading like a green waterfall – it's Wisconsin's answer to the Hanging Gardens of Babylon, minus the ancient mystery.
Gardens cascading like a green waterfall – it’s Wisconsin’s answer to the Hanging Gardens of Babylon, minus the ancient mystery. Photo Credit: Jon Chandler

Our first stop is the Villa Terrace Decorative Arts Museum in Milwaukee, a stunning example of Mediterranean-style architecture that will have you wondering if you’ve accidentally teleported to the Italian Riviera.

This elegant mansion, perched atop a bluff overlooking Lake Michigan, boasts a breathtaking Renaissance garden that would make even the most seasoned landscape architect weep with joy.

As you ascend the grand staircase, you’ll feel like you’re climbing the social ladder of the 1920s elite.

2a. villa terrace decorative arts museum (milwaukee)2a. villa terrace decorative arts museum (milwaukee)
Lake Michigan or the Mediterranean? This Italian dream makes you wonder if you’ve stumbled into Clooney’s Lake Como villa. Photo Credit: Nate

The villa’s interior is a treasure trove of decorative arts, featuring intricate ironwork, ornate furnishings, and enough marble to make a Roman emperor feel right at home.

Don’t miss the opportunity to strike a pose on the terrace, channeling your inner silent film star as you gaze out over the lake.

Just remember, old sport, no jumping into the fountain – we’re here to admire the art, not recreate scenes from “The Great Gatsby.”

2. Pabst Mansion (Milwaukee)

Gilded Age glamour meets beer baron bling! This sandcastle-on-steroids proves hops can build more than just hangovers.Gilded Age glamour meets beer baron bling! This sandcastle-on-steroids proves hops can build more than just hangovers.
Gilded Age glamour meets beer baron bling! This sandcastle-on-steroids proves hops can build more than just hangovers. Photo Credit: Amanda McGrady

Next up on our Jazz Age journey is the Pabst Mansion, a testament to the fact that beer barons knew how to live large.

This Gilded Age gem might predate the Roaring Twenties, but it’s got enough opulence to make any flapper swoon.

As you approach the mansion, you’ll be greeted by a façade that screams “I’ve got more money than I know what to do with” – in the most tasteful way possible, of course.

Step inside, and you’ll find yourself surrounded by more gold leaf than Fort Knox.

The Pabst family clearly believed that if something was worth doing, it was worth overdoing.

Step into Milwaukee's crown jewel, where every inch screams 'I've got 99 problems, but a beer ain't one!Step into Milwaukee's crown jewel, where every inch screams 'I've got 99 problems, but a beer ain't one!
Step into Milwaukee’s crown jewel, where every inch screams ‘I’ve got 99 problems, but a beer ain’t one! Photo Credit: Nan W

From the ornate ceilings to the intricately carved woodwork, every inch of this mansion is a testament to the excesses of the era.

As you wander through the rooms, imagine the lavish parties that could have been held here during Prohibition.

Who knows?

You might even stumble upon a secret speakeasy hidden behind a bookcase.

3. Ten Chimneys (Genesee Depot)

Broadway's summer retreat in rural Wisconsin – where the corn's as high as an elephant's eye, and the drama's even higher!Broadway's summer retreat in rural Wisconsin – where the corn's as high as an elephant's eye, and the drama's even higher!
Broadway’s summer retreat in rural Wisconsin – where the corn’s as high as an elephant’s eye, and the drama’s even higher! Photo credit: Kevin Nunn

Our next stop takes us to the charming village of Genesee Depot, where we’ll visit Ten Chimneys, the summer home of Broadway legends Alfred Lunt and Lynn Fontanne.

This estate is like a theatrical production come to life, with each room more dramatically decorated than the last.

It’s as if the Jazz Age and Broadway had a love child, and that child grew up to be a house.

As you tour the property, you’ll discover why it’s called Ten Chimneys – spoiler alert, there are indeed ten chimneys.

A theatrical fever dream in the countryside. Expect floral patterns galore and maybe a dramatically posed actor behind every curtain.A theatrical fever dream in the countryside. Expect floral patterns galore and maybe a dramatically posed actor behind every curtain.
A theatrical fever dream in the countryside. Expect floral patterns galore and maybe a dramatically posed actor behind every curtain. Photo credit: peter the lesser

But the real magic lies in the eclectic mix of styles and the personal touches left by the Lunts.

From the whimsical murals to the stage-inspired design elements, this place is a feast for the eyes and the imagination.

Just resist the urge to break into a spontaneous musical number – unless, of course, you’re prepared to receive a standing ovation from your fellow tourists.

4. Hearthstone Historic House Museum (Appleton)

Edison's bright idea comes to life! This Victorian beauty was doing electricity before it was cool – talk about being ahead of the curve.Edison's bright idea comes to life! This Victorian beauty was doing electricity before it was cool – talk about being ahead of the curve.
Edison’s bright idea comes to life! This Victorian beauty was doing electricity before it was cool – talk about being ahead of the curve. Photo credit: Rob Hoehn

Illuminating our journey is the Hearthstone Historic House Museum in Appleton, the first home in the world to be lit by a centrally located hydroelectric station using the Edison system.

Talk about being ahead of the curve!

This Victorian mansion might have predated the Jazz Age, but it was certainly lighting the way for the innovations to come.

As you explore the house, you’ll be struck by the blend of Victorian elegance and cutting-edge (for the time) technology.

It’s like stepping into a steampunk novel, minus the airships and clockwork robots.

Queen Anne meets mad scientist chic. Those original light fixtures are steampunk chandeliers straight out of a sci-fi novel.Queen Anne meets mad scientist chic. Those original light fixtures are steampunk chandeliers straight out of a sci-fi novel.
Queen Anne meets mad scientist chic. Those original light fixtures are steampunk chandeliers straight out of a sci-fi novel. Photo credit: Kim Racchini

The original light fixtures are still in place, serving as a reminder of how far we’ve come from the days of candlelight and gas lamps.

Just imagine the look on guests’ faces when they first saw electric lights flickering to life – it must have been like witnessing magic.

And let’s be honest, in the age of smartphones and Wi-Fi, we could all use a reminder of how awe-inspiring a simple light bulb can be.

5. Black Point Estate and Gardens (Lake Geneva)

Chicago beer baron's 'modest' summer cottage. With 20 rooms and lake views, it's the Midwest's answer to Newport mansions.Chicago beer baron's 'modest' summer cottage. With 20 rooms and lake views, it's the Midwest's answer to Newport mansions.
Chicago beer baron’s ‘modest’ summer cottage. With 20 rooms and lake views, it’s the Midwest’s answer to Newport mansions. Photo credit: Aaron Carlson

Our Jazz Age journey takes a luxurious turn as we arrive at Black Point Estate and Gardens in Lake Geneva.

This summer “cottage” (and I use that term loosely) of Chicago beer baron Conrad Seipp is the epitome of Gilded Age extravagance with a dash of Roaring Twenties flair.

Perched on the shores of Geneva Lake, this mansion is so grand it makes other mansions feel like they should be living in tiny houses.

As you approach by boat, you’ll be struck by the sheer size of the place.

It’s as if someone took a normal house and hit the “supersized” button.

Time-capsule of 1888 design with a view that'll make you forget you're not in the Hamptons. Handlebar mustaches optional, but encouraged.Time-capsule of 1888 design with a view that'll make you forget you're not in the Hamptons. Handlebar mustaches optional, but encouraged.
Time-capsule of 1888 design with a view that’ll make you forget you’re not in the Hamptons. Handlebar mustaches optional, but encouraged. Photo credit: Najuan Mack

The Queen Anne-style architecture is a feast for the eyes, with more gables, turrets, and wraparound porches than you can shake a champagne flute at.

Inside, the 20 rooms are decked out in period furnishings that will make you want to don a flapper dress or a dapper suit and start Charleston-ing across the hardwood floors.

Just remember, if you hear someone calling for Gatsby, it’s probably just your imagination… or is it?

6. Fairlawn Mansion (Superior)

Lumber baron's flex turned children's home. It's like Annie, if Miss Hannigan's orphanage was actually a castle!Lumber baron's flex turned children's home. It's like Annie, if Miss Hannigan's orphanage was actually a castle!
Lumber baron’s flex turned children’s home. It’s like Annie, if Miss Hannigan’s orphanage was actually a castle! Photo credit: Nick Bahr

Our next stop takes us to the shores of Lake Superior, where the Fairlawn Mansion stands as a testament to the fact that lumber barons knew how to live it up just as much as their beer-brewing counterparts.

This Queen Anne Victorian might have been built before the Jazz Age, but it’s got enough pizzazz to fit right in with our Roaring Twenties theme.

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As you approach the mansion, you’ll be struck by its imposing tower – perfect for keeping an eye out for Prohibition agents or rival lumber barons.

Victorian fever dream in Superior, Wisconsin. So much gingerbread trim, you'll wonder if it's edible. (Spoiler: it's not).Victorian fever dream in Superior, Wisconsin. So much gingerbread trim, you'll wonder if it's edible. (Spoiler: it's not).
Victorian fever dream in Superior, Wisconsin. So much gingerbread trim, you’ll wonder if it’s edible. (Spoiler: it’s not). Photo credit: Jeffrey Koenen

The exterior is a delightful mishmash of architectural styles, as if the designer couldn’t decide on just one and said, “Eh, let’s use them all!”

Inside, you’ll find yourself surrounded by opulent furnishings and enough wood to make you feel like you’ve stepped into a very fancy forest.

The mansion later served as an orphanage, so feel free to channel your inner Annie as you explore – just don’t expect Miss Hannigan to come bursting through the door.

7. Taliesin (Spring Green)

Frank Lloyd Wright's architectural mixtape. Part house, part sculpture, all genius – with a dash of 'how do I furnish this?Frank Lloyd Wright's architectural mixtape. Part house, part sculpture, all genius – with a dash of 'how do I furnish this?
Frank Lloyd Wright’s architectural mixtape. Part house, part sculpture, all genius – with a dash of ‘how do I furnish this? Photo credit: Elizabeth Shniper

Hold onto your cloche hats, folks, because our next stop is Taliesin, the home and studio of architectural maverick Frank Lloyd Wright.

Now, I know what you’re thinking – “Frank Lloyd Wright? Wasn’t he more mid-century modern than Jazz Age?”

Well, my dear Watson, you’d be right, but Taliesin’s story spans decades, including the Roaring Twenties, making it a perfect pit stop on our Jazz Age journey.

As you approach this architectural wonderland, you’ll notice that it seems to grow organically from the hillside, like some sort of geometric mushroom.

Organic architecture at its finest. It's like Mother Nature and geometry had a love child, and Wright was the proud papa.Organic architecture at its finest. It's like Mother Nature and geometry had a love child, and Wright was the proud papa.
Organic architecture at its finest. It’s like Mother Nature and geometry had a love child, and Wright was the proud papa. Photo credit: Brendan Gotch

Wright’s philosophy of organic architecture is on full display here, with the building seamlessly blending into its surroundings.

It’s as if Mother Nature decided to try her hand at architecture after a few too many gin rickeys.

Inside, you’ll find yourself in a world where right angles fear to tread and windows are more abundant than a speakeasy’s liquor supply.

Just remember, if you hear someone muttering about the “destruction of the box,” it’s probably just the ghost of Frank Lloyd Wright, still tinkering with his masterpiece.

8. Villa Louis (Prairie du Chien)

8a. villa louis (prairie du chien)8a. villa louis (prairie du chien)
Mississippi River mansion that screams ‘We’ve made it!’ in multiple architectural languages. It’s the polyglot of prairie houses. Photo credit: Dan Diener

Our Jazz Age jaunt now takes us to Villa Louis in Prairie du Chien, a mansion that’s seen more renovations than a Hollywood starlet.

Built in the 1840s and remodeled in the 1870s, this Victorian-era beauty might predate the Roaring Twenties, but it’s got enough style to hang with the Jazz Age crowd.

As you approach the mansion, you’ll be struck by its stately presence – it’s the kind of place that makes you want to straighten your tie or adjust your pearls, even if you’re wearing neither.

Step into a Victorian time capsule where the kitchen gadgets look like steampunk inventions. Your Instant Pot could never.Step into a Victorian time capsule where the kitchen gadgets look like steampunk inventions. Your Instant Pot could never.
Step into a Victorian time capsule where the kitchen gadgets look like steampunk inventions. Your Instant Pot could never. Photo credit: Cori Ring

Inside, you’ll find yourself surrounded by a treasure trove of original furnishings and decorative arts that would make any antique dealer swoon.

The Dousman family, who called this place home, clearly had a flair for the dramatic when it came to interior design.

As you wander through the rooms, imagine the soirées that could have been held here during the Prohibition era – just don’t go looking for any hidden liquor stashes.

The staff frowns upon that sort of thing.

9. Hixon House (La Crosse)

Italianate showstopper in La Crosse. It's the architectural equivalent of wearing a tuxedo to a backyard barbecue – and pulling it off!Italianate showstopper in La Crosse. It's the architectural equivalent of wearing a tuxedo to a backyard barbecue – and pulling it off!
Italianate showstopper in La Crosse. It’s the architectural equivalent of wearing a tuxedo to a backyard barbecue – and pulling it off! Photo credit: Daniel Walters

Next on our whirlwind tour of Wisconsin’s Jazz Age-adjacent marvels is the Hixon House in La Crosse.

Now, I know what you’re thinking – “Another Victorian mansion? Didn’t the Jazz Age have its own architectural style?”

Well, dear reader, the Roaring Twenties were all about reinvention, so consider this stop a before-and-after snapshot of American luxury.

As you approach this Italianate-style beauty, you’ll notice it’s got more angles than a geometry textbook and more decorative brackets than a librarian’s wildest dreams.

Victorian hoarder's paradise with a mirror so fancy, it probably judges you. Marie Kondo would have a field day here.Victorian hoarder's paradise with a mirror so fancy, it probably judges you. Marie Kondo would have a field day here.
Victorian hoarder’s paradise with a mirror so fancy, it probably judges you. Marie Kondo would have a field day here. Photo credit: Don Davidson

Inside, you’ll find yourself transported to a world where “more is more” was the design philosophy du jour.

The Hixon family clearly never met a pattern they didn’t like – from the wallpaper to the carpets, it’s a veritable symphony of visual stimulation.

Just be careful not to stare at any one surface for too long, or you might find yourself hypnotized by the swirling designs.

And whatever you do, resist the urge to touch the vintage velvet – no matter how tempting it may be.

10. Rahr-West Art Museum (Manitowoc)

Queen Anne mansion meets modern art gallery. It's like your cool grandma who rocks out to Bowie and has a secret tattoo."Queen Anne mansion meets modern art gallery. It's like your cool grandma who rocks out to Bowie and has a secret tattoo."
Queen Anne mansion meets modern art gallery. It’s like your cool grandma who rocks out to Bowie and has a secret tattoo.” Photo credit: Sharon Spoelstra

Our final stop on this Jazz Age journey is the Rahr-West Art Museum in Manitowoc, housed in a mansion that’s seen more transformations than a Transformer.

Built in 1893, this Queen Anne-style home has worn many hats over the years – from family residence to art museum – much like a flapper changing her hairstyle with the seasons.

As you approach the mansion, you’ll be struck by its eclectic charm.

It’s as if someone took a Victorian dollhouse and said, “You know what this needs? A turret!”

Where Picasso hangs out in Victorian parlors. The ultimate 'old meets new' – think 'Downton Abbey' hosting a Warhol exhibition.Where Picasso hangs out in Victorian parlors. The ultimate 'old meets new' – think 'Downton Abbey' hosting a Warhol exhibition.
Where Picasso hangs out in Victorian parlors. The ultimate ‘old meets new’ – think ‘Downton Abbey’ hosting a Warhol exhibition. Photo credit: Asbel Cedillo

Inside, you’ll find a delightful mash-up of historic architecture and modern art exhibitions.

It’s like stepping into a time machine that can’t quite decide which era it wants to land in.

As you wander through the galleries, keep an eye out for any ghostly flappers or dapper gents – they might just be art enthusiasts from the Roaring Twenties who got a bit too enthusiastic about time travel.

Well, old sports, our Jazz Age journey through Wisconsin has come to an end.

Time to trade in that Rolls-Royce for a sensible sedan and return to the present day.

Adventure is calling!

Use this map to steer your road trip in the right direction—and maybe discover a surprise or two along the way.

wisconsin historic homes trip mapwisconsin historic homes trip map

But fear not – the spirit of the Roaring Twenties lives on in these magnificent mansions, ready to transport you back in time whenever you need a dose of glamour and gin (figuratively speaking, of course).





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