Trips & Routes

Small Towns

Trips & Routes
Small Towns

Why Travelers Are Falling for This Small Historic Town in Wisconsin

Sturgeon Bay is a small historic town in Wisconsin. With shipbuilding roots and plenty of local culture, it's a perfect jumping off point for Door County.

by Cait Kontalis
on Mar 31
A lighthouse and pier in Wisconsin
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The Coastal Wisconsin Town Locals Hope Stays Off Tourists’ Radar

by Trent Jonas
on Mar 10
The Ashland Breakwater Lighthouse sits on a long stone pier surrounded by the blue waters of Chequamegon Bay, WI.
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This Wisconsin Lakeside Town Feels Like the Northeast in the Fall and It’s Stunning

by Cait Kontalis
on Nov 7
A dock extending out into a lake with trees surrounding the lakefront in Wisconsin.
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Discover the Wisconsin Small Town That Looks Like a Hallmark Movie Set

by Amanda Finn
on Oct 30
A close up of the ivory stone exterior of Taliesin with a small pool in the foreground.
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The Small Town in Wisconsin With ‘That ’70s Show’ Vibes

by Trent Jonas
on Apr 9
Cars line the bustling street of a historic downtown area with red brick and stone buildings in a small Wisconsin city.

Latest Small Towns

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Small Towns

This Tiny Town in Wisconsin Feels Like a Living Time Capsule

Ready to step back in time? Discover old-timey favorites like supper clubs, Victorian-era homes, and maritime history in Sturgeon Bay, Wisconsin.

by Cait Kontalis
on Apr 10
A bridge crossing a river with a town and a hill behind it.
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Small Towns

Greetings From Dousman, Wisconsin: A Town With a Hoppin’ Tradition

This town's love of frogs is straight out of a Mark Twain story.

by Amanda Finn
on Sep 3
A young girl with a pony tail kneeling behind a jumping frog
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Small Towns

This Swiss-Inspired Village in Wisconsin Feels Like a Slice of the Alps

This Wisconsin town seemingly transports visitors on a dreamy trip to Europe without ever needing to board an airplane.

by Molly O'Brien
on Aug 25
Men dressed in traditional clothes play in New Glarus
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Small Towns

Why Baraboo, Wisconsin, the Gateway of Devil’s Lake State Park, Is Worth a Visit in Its Own Right

Spend some time in nature, and then visit the clowns in Baraboo.

by Kerri Cox
on Jun 27
A row of colorful historic buildings line a small town square in Baraboo, WI
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Small Towns

Skip Europe This Summer: This Village in Wisconsin Is Just as Charming as Germany

Germantown, Wisconsin, is the oldest town in its county. With a deep German heritage, the charming village still celebrates its culture with food, fun, and history.

by Amanda Finn
on May 9
Von Rothenburg Bier Stube in Germantown, Wisconsin.
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Small Towns

Why Winter Is This Charming Wisconsin’s Town Secret Season

With snow sports and dining options, as well as nearby natural areas for hiking, snow shoeing, and cross-country skiing, Dresser is one of the best winter towns in Wisconsin

by Trent Jonas
on Dec 19
Skiers and snowboarders descend a snow-covered hill next to a ski lift under a clear winter sky.
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Small Towns

There’s No Place Like My Hometown of Westby, Wisconsin for the Holidays

This winter, check out the single coolest (literally) small town in Wisconsin that's perfect for the holiday season.

by Tori Jane
on Nov 26
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Small Towns

The Remote Town in Wisconsin We Simply Can’t Get Enough of

Nestled along Lake Superior, this charming town offers scenic trails, kayaking, and breathtaking views. It also boasts cozy dining spots with local flavors, making it an ideal destination for nature lovers and foodies alike.

by Jacki Mick
on Nov 16
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Small Towns

The Remote Town in Wisconsin We Simply Can’t Get Enough Of

History buffs, outdoor lovers, and those who just want to explore someplace new will fall in love with Berlin, Wisconsin.

by Courtnie Erickson
on Nov 1
Colorful historic buildings line a street, featuring a distinctive clock tower and vibrant storefronts under a clear blue sky.
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Small Towns

If You Only Have One Day to Visit This Small Town in Wisconsin, Here Are 3 Things You Absolutely Can’t Miss

If you're looking for day trip ideas in the Badger State, we think you'll love Osceola as a small town getaway in Wisconsin.

by Trent Jonas
on Oct 29
A serene waterfall cascades over rocks, surrounded by vibrant autumn foliage in a peaceful natural setting.
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Small Towns

This Blink-and-You’ll-Miss-It Town in Wisconsin Is So Worth Exploring

Ellsworth, a charming small town in Wisconsin, is the self-proclaimed "Cheese Curd Capital."

by Trent Jonas
on Sep 19
A sign declares Ellsworth, WI "The Cheese Curd Capital."
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Small Towns

The Best Small Town Getaway In Wisconsin: Best Things To Do In Bayfield

by Trent Jonas
on Jul 18
A scenic view of a waterfront town with lush green hills, boats docked, and charming houses along the shore.
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Small Towns

There’s A Famous Urinal In Wisconsin, And It’s One Of The Quirkiest Places You’ll Ever Go

by Ben Jones
on Jan 11
A colorful banner reading "Welcome to Big Dick's Buckhorn Inn" hangs above a lively bar scene with patrons.
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Small Towns

Cable Wisconsin Is The Perfect Midwest Winter Travel Destination

by Ben Jones
on Jan 4
A green sign reading "Cable UNINCORPORATED" surrounded by snow-covered trees.
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Small Towns

The Cozy Small Town In Wisconsin That Comes Alive Under A Blanket Of Snow

by Ben Jones
on Dec 14
Sign welcoming visitors to Winter, featuring a tribute to astronaut Jeff Williams and snowy surroundings.
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Small Towns

Chilton, Wisconsin Is The Very Definition Of Small Town Charm

by Ben Jones
on Dec 12
A parade scene with participants carrying a banner for the Chilton Chamber of Commerce, surrounded by spectators.
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Small Towns

This Charming Community Might Just Be The Most Peaceful Place To Live In Wisconsin

by Ben Jones
on Nov 17
Silhouettes of people and a dog by the water at sunset, with vibrant colors reflecting on the calm surface.
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Small Towns

Tiny Brodhead, Wisconsin Is A Time Capsule Town That’s Irresistibly Charming And Nostalgic’

by Ben Jones
on Nov 12
A charming town square with a gazebo, flower beds, and historic buildings under a blue sky with scattered clouds.
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Small Towns

7 Christmas Towns In Wisconsin That Will Fill Your Heart With Holiday Cheer

by Ben Jones
on Nov 8
A brightly lit boat with colorful lights glides across a calm lake at dusk, reflecting on the water.
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Small Towns

This Little-Known Scenic Spot In Wisconsin that Comes Alive With Color Come Fall

by Ben Jones
on Nov 3
A line of ATVs travels down a dirt path through a vibrant autumn forest with colorful leaves.
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Small Towns

The Remote Small Town in Wisconsin Locals Don’t Want You to Find

Looking to get away from it all? You'll find plenty of fun adventures and things to do in Washington Island, Wisconsin.

by Beth Copenhaver
on Oct 19
Red boathouses line the shore at Jackson Harbor on Washington Island, Door County, Wisconsin.
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Small Towns

The Most Charming College Town In Wisconsin Is Home To Delicious Dining, Shopping And More

by Ben Jones
on Oct 3
Two classic cars, a red convertible and a silver sports car, drive through a charming downtown street with historic buildings.
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Small Towns

Enjoy The Simple Life When You Visit This Tiny Rural Community In Wisconsin

by Ben Jones
on Sep 29
A charming stone building with a small cottage and a sign, surrounded by greenery and flowers.
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Small Towns

One Of The Most Historic Small Towns In Wisconsin Is Also Among The Most Haunted

by Ben Jones
on Sep 19
A stone building with multiple windows and a sign reading "Mansfield House" surrounded by trees and a pathway.
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Small Towns

The Small Town in Wisconsin That Comes Alive in the Fall Season

Baraboo is a Wisconsin small town that comes alive in autumn. See the leaves changing color, go apple picking, or ride a nearby train.

by Rachel Pfutzenreuter
on Oct 5
A vibrant autumn tree viewed from below, showcasing bright orange and yellow leaves against a clear blue sky.
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Small Towns

The Charming Small Town in Wisconsin That’s Perfect For A Fall Day Trip

Cassville, Wisconsin, offers vibrant fall foliage, historic sites, and scenic views, making it an ideal fall day trip destination.

by Ben Jones
on Sep 9
Aerial view of a river at sunset, reflecting vibrant colors, with a small town and green hills in the background.
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Small Towns

Enjoy The Simple Life When You Visit This Tiny Rural Community In Wisconsin

Clam Lake in Wisconsin offers outdoor activities, elk viewing, and a simple rural lifestyle.

by Rachel Pfutzenreuter
on Aug 2
A large elk with impressive antlers walks through a lush green landscape.
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Small Towns

There’s No Community In Wisconsin More Enchanting And Historic Than Ellison Bay In Wisconsin

Ellison Bay in Wisconsin offers a blend of beauty and history, making it a perfect getaway with scenic views, historic sites, and outdoor activities.

by Ben Jones
on Jul 28
A serene beach scene with gentle waves, sandy shore, and lush trees lining the coastline under a soft sunset sky.
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Small Towns

Most People Don’t Even Know This Little-Known Destination In Wisconsin Even Exists

Rowleys Bay in Door County, Wisconsin, offers a peaceful retreat with scenic nature, hiking trails, and paddling opportunities.

by Ben Jones
on Jul 26
Aerial view of a lakeside resort with parking, docks, and colorful kayaks, surrounded by trees and a sunset glow.
Trips & Routes
Small Towns

The Rutabaga Capital of Wisconsin Is One of the Most Charming Small Towns You’ll Ever Visit

Discover Cumberland, Wisconsin, a charming lakeside town known as the Rutabaga Capital of Wisconsin. Explore outdoor adventures, local shops, and a beloved annual festival.

by Ben Jones
on Jun 9
View across the lake toward the town of Cumberland, Wisconsin, featuring green trees and storefronts.
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Small Towns

With a Farmers Market, Weekly Music, and Seasonal Festival, There’s Nothing Like a Summer Weekend in This Wisconsin Town

Shawano is livelier than ever, with gorgeous outdoor concerts and more. It's a seriously underrated Wisconsin getaway spot.

by Ben Jones
on May 19
A colorful mural reading "Greetings from Shawano" on a city street in Wisconsin.
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Small Towns

The Ice Age Trail Runs Through This Wisconsin Town And It’s The Ultimate Outdoor Playground

Two Rivers, Wisconsin, is a charming lakefront city known for its outdoor activities, including hiking, biking, and water sports.

by Ben Jones
on Jul 4
A serene waterfront scene featuring a sandy beach, a white house, and buildings in the background under a clear sky.
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Small Towns

You Could Spend Forever Exploring This Wisconsin Small Town, But We’ll Settle For A Weekend

New Glarus, Wisconsin, offers a Swiss-inspired experience with vibrant festivals, outdoor activities, and unique culinary delights.

by Ben Jones
on Apr 19
A cyclist in an orange shirt rides past a historic train station labeled "New Glarus" on a sunny day.
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Small Towns

A Charming and Historic Small Town in Wisconsin, Charlesburg Is Seemingly Frozen in Time

Charlesburg, Wisconsin is a historic and serene farming community known for its old church and popular supper club.

by Ben Jones
on Jan 20
The front facade of a historic stone church in Charlesburg, Wisconsin, featuring a tall steeple and Gothic architecture set against a cloudy twilight sky.
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Small Towns

One Of The Biggest Names In TV Grew Up In One Of The Smallest Towns In Wisconsin

by Ben Jones
on May 20
A quaint brick building with green doors and a white staircase, surrounded by trees and a quiet street.
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Small Towns

A Tiny Farm Town In Wisconsin, Viroqua Is A Midwest Food Destination

Viroqua, Wisconsin, is a small town known for its exceptional local food scene and organic farming cooperatives.

by Nicole Haase
on May 15
A family stands together, overlooking a lush green farm and rolling hills under a clear sky.
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Small Towns

Hike Up A Hidden Mountain Then Dine At A Small-Town Cafe On This Delightful Adventure In Wisconsin

Discover a rewarding adventure in Wisconsin with a hike up McCaslin Mountain followed by a meal at Karla’s Kitchen.

by Ben Jones
on May 9
A scenic view of a forest in autumn, showcasing vibrant yellow and orange foliage under a cloudy sky.
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Small Towns

You Could Spend Forever Exploring This Wisconsin Small Town, But We’ll Settle For A Weekend

Lake Geneva, Wisconsin, is a charming resort town offering a variety of outdoor activities, dining options, and seasonal events.

by Megan Todaro
on Apr 19
A scenic view of a marina with boats on blue water, surrounded by trees and buildings under a clear blue sky.
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Small Towns

The Small Wisconsin Town Of Baileys Harbor Has More Outdoor Attractions Than Any Other Place In The State

Baileys Harbor in Door County, Wisconsin offers a variety of outdoor activities including shipwreck diving, sea kayaking, hiking, and zip lining.

by Ben Jones
on May 7
A group of kayakers paddles in clear blue water near a rocky shore under a bright blue sky.
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Small Towns

This Wisconsin Town Is One Of The Most Peaceful Places To Live In The Country

by Ben Jones
on Apr 11
Aerial view of a small town with residential homes, shops, and trees, showcasing a peaceful community setting.
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Small Towns

Just 30 Minutes From Milwaukee, Port Washington Is The Perfect Wisconsin Day Trip Destination

Port Washington, Wisconsin, offers a rich history, beautiful waterfront, quaint stores, and delicious restaurants, making it a perfect day trip destination.

by Ben Jones
on Apr 22
A scenic view of a small town street with shops, featuring a prominent clock tower in the background under a clear blue sky.
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Small Towns

You Can Live Off The Grid In This Wisconsin Town Considered The Best In The Country

Hayward, Wisconsin offers a blend of wild forests, outdoor recreation, and small-town comforts, making it an ideal spot for off-grid living.

by Ben Jones
on Mar 15
Sunset over a calm lake, framed by tall trees and a serene forest landscape.
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Small Towns

Here Are The Most Beautiful, Charming Small Towns In Wisconsin

Highlights the best small towns in Wisconsin known for their safety, community, and affordable lifestyle.

by Laura Meli
on Mar 10
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Small Towns

Visit The Friendliest Town In Wisconsin The Next Time You Need A Pick-Me-Up

Alma, Wisconsin, is a charming and friendly small town along the Mississippi River with beautiful views, excellent dining, and bird-watching opportunities.

by Courtnie Erickson
on Mar 13
Aerial view of a river winding through lush greenery, with a small town visible along the riverbank.
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Small Towns

The Perfect Sturgeon Bay Day Trip Itinerary – Not Your Average Bucket List Episode 14

Sturgeon Bay, Wisconsin, is a historic coastal town known for its maritime heritage, beautiful beaches, and outdoor activities.

by Marisa Roman
on Feb 24
Aerial view of a marina with numerous boats docked, surrounded by buildings and greenery.