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If you live in Milwaukee and are looking for a place to escape the hustle and bustle, there’s a small town easily within reach that is overflowing with charm and a more relaxed pace. Whether you’re in the mood for a chance to discover rich history, time on a trail, or a European getaway without your passport you’re sure to find what you’re looking for in one of the 5 small Wisconsin towns we feature below. Plus, each of the 5 towns in this post have the cutest main street often with original architecture, fascinating history, and shopping experiences rife with local gems. The best part? All are a 2-hour drive or less from Milwaukee and span across eastern, central and western Wisconsin.
Be sure to check out the “special time to visit” note for each of these 5 towns in case you want to plan ahead and make your small-town visit even more memorable.
Eastern Wisconsin
Cedarburg
Distance from downtown Milwaukee: 30 minutes
Cedarburg has loads of history and heaps of charm which you’ll pick up on right away when you take a scenic stroll down Cedarburg’s main street. Often heralded as one of the best burbs of Milwaukee, Cedarburg is a place where American flags wave patriotically and you will want to take your time exploring. Wander in and out of electric shops & confectionaries on the main street. Enjoy the hospitality and friendly conversation with strangers. Be sure to stop at the Gem Shop for beautiful crystals and a free postcard! The Historic Cedarburg Wisconsin Wall Art located right off the main street is a great spot to snap a selfie to let everyone know where you were. Walk across the historic, Interurban bridge and along Cedar Creek for nice water and nature views. After a pleasant stroll, sit on the patio at Rebellion Brewery and enjoy a cold, craft beer. Or grab a meal at Stilt House Gastro Bar where you can admire the historic buildings while dining al fresco, weather permitting.
A special time to visit: For an everlasting memory of Cedarburg, make sure to visit during their annual Strawberry Fest held in June or during one of their Maxwell Street Day events. We have been coming to hunt treasures during Maxwell Street Days on and off for years now. These events are the largest fundraiser for the local Cedarburg Fire Department and will keep you busy for a full day as you enjoy browsing rows and rows of open-air tents and tables laden with treasures. There’s plenty of food and drink vendors on-site as well but you can certainly bring your own food and drink or head into town and enjoy a great meal at a local restaurant.
Port Washington
Distance from downtown Milwaukee: 30 minutes
This picture-perfect lakeside, harbor town is home to a quaint Main Street filled with saloons and shops of all sorts. Must stops include the Port Washington Marina and the 1860 Lighthouse and Light Station Musuem. Spending time on the lake, soaking up the beautiful landscape and marina from the water, is an activity worth seriously considering while visiting. In town, you’ll find several different boating and charter companies ready to take you out on the lake for a memorable fishing trip.
For those seeking to spend time in Wisconsin’s great outdoors while in town, you’ll find North Beach and South Beach in Port Washington – both perfect for a day of swimming and picnicking. About 4 miles south of Port Washington you’ll find Lion’s Den Gorge which guarantees spectacular view of Lake Michigan and its shoreline. Harrington Beach State Park, located about 10 miles north of Port Washington in Belgium, Wisconsin offers a mile-long beach, white cedar swamp and hiking trails.
A special time to visit: Memorial Day weekend (end of May)
Central Wisconsin
Verona
Distance from downtown Milwaukee: 1 hour and 22 minutes
While you will undoubtedly be eager to enjoy the culture and food in Verona, one of the best features of this town are the outdoor adventures right at your doorstep. Nestled along the National Scenic Ice Age Trail, Verona is the perfect spot for a weekend hiking trip. While there are plenty of reasons to visit Verona year-round, the hiking scene here truly shines in the fall. Immerse yourself in nature and hike against a backdrop of yellow, terracotta, orange and red. It’s a wonderful, suburban segment that will lead you past wetlands and kettle ponds, sand-dusted rolling prairies and classic Driftless area landscapes. Beyond the natural beauty you’ll find on this trail, you’ll also get to experience a vibrant Ice Age Trail community. That’s right, this trail takes you straight into the heart of Verona. While you’re trekking along Badger Mill Creek you are hiking parallel to Verona’s Main Street.
The Main Street is utterly charming with colorful storefronts, murals and antique signage. You’ll find a great food scene here. Choose from fresh sushi at Miller & Son’s, seasonal dishes at The Sow’s Ear and giant soft pretzel with a locally brewed IPA at Hop Haus.
A special time to visit: The Fall! Check out our Fall Bucket List: Verona, Wisconsin blog post to find out why the fall season is the best time to visit Verona.
Western Wisconsin
New Glarus
Distance from downtown Milwaukee: 1 hour and 41 minutes
With just over 2,000 residents, New Glarus, Wisconsin is truly the stereotypical image of small-town Americana with a major European twist. Boasting all the charm and character of Switzerland without a need for a transatlantic flight, New Glarus is one of Wisconsin’s most charming towns. Affectionately referred to as “America’s Little Switzerland” a visit here is like stepping into a Swiss postcard with its alpine architecture and chocolatiers selling Swiss delicacies. In the summer, visitors come to hike and bike on the Sugar River State Trail which connects New Glarus to Monticello, Albany and Brodhead. You’ll also find plenty of breweries and local shops to explore, not to mention an annual Oktoberfest celebration; there’s always something to do in New Glarus.
A special time to visit: Early January for their annual Silvesterchlausen New Year’s celebration or any time the award-winning New Glarus Brewing Company is open!
Mineral Point
Distance from downtown Milwaukee: 2 hours
Located in the heart of Wisconsin’s Driftless Region is where you will find Mineral Point. This fascinating town is bursting with history and an artistic enclave unlike any other in the state. It’s one of the oldest places in Wisconsin (established in 1827) and the lands that make up Mineral Point were once rich in lead and zinc which contributed to the town once being an important mining hub.
Spend a full day or even longer traveling back in time here. Acquaint yourself with the town’s history on an architectural walking tour down its Main Street. Discover the town’s Cornish origins – which run very deep. You will find Cornish influence in many aspects of Mineral Point from the nearly 500 preserved historic buildings and sites around town – most in traditional Cornish architectural style – to the cozy, comfort foods like figgyhobbin and pasty pies served up at the popular Red Rooster Café. Visit Pendarvis, a Wisconsin Historic Site, and enjoy the fresh air on the 43-acre Merry Christmas Mine Hill Trail and Prairie where you can stop along the way at different points of interest that hold particular significance to the land and it’s past as a major mining site.
Beyond its special place in Wisconsin’s history books, Mineral Point is truly a town of makers. Immerse yourself in the creativity of the place by visiting the many art galleries or visiting Shake Rag Alley Center for the Arts – a hub of creativity spread across 2.5 acres and set in an idyllic setting with several historic buildings.
You’ll also find that good ‘ol Midwestern hospitality at every place you stop!
A special time to visit: Early December for the Candlelight Shopping Experience. Each year Mineral Point transforms into a magical wonderland with mega holiday spirit. During the event, take in the mesmerizing luminaries lining the downtown and the smell of roasting chestnuts while visiting unique small shops and pop-ups all open late for the event.
Honestly, we’ve never met a Wisconsin town we haven’t loved exploring and getting to know firsthand. Our home state is so much more than cheese curds and cows. As the five towns featured in this post show, we have little pockets of European history, unique architecture, quaint main streets, festivals unlike any other in the nation and even mines! There is no shortage of places to enjoy a memorable day trip while you’re in Wisconsin, but these are 5 of our favorites within easy driving distance of Milwaukee which is our home base.
We wish you happy travels as you explore these towns and beyond on your next day trip around the badger state!
~ Justin + Alyssa
Interesting looking places.
Each are very unique! Do you like checking out small towns around where you live?
Yes we do – well, most places are small in New Zealand!
How alluring! We’re currently on our second ever US road trip and we have to say that the small town stops are a huge part of the enjoyment. Every one has something special…plus, as British visitors, those stops make us feel like we’re doing a road trip “properly”, if you know what I mean.
We’ve really enjoyed following along as you road trip in the US and are happy you’ve made it part of your mission to visit our charming small towns. There is beauty in each and every place, you just have to know where to look or give a place a chance 🙂
More to follow on that subject shortly!
A strawberry feast sounds like loads of fun! And I think we’ll love Verona with the hiking trail as the big attraction. You are privileged to have such beautiful places near your hometown. And I agree … it’s the little towns that are usually the gems and great to explore!
Thanks for reading this post and glad to learn you too are a fan of small towns. We really are fortunate to have SO many beautiful places close to home.
I never heard of such a thing aa the Ice Age Trail let alone any of the small towns you mentioned in your post. You should be appointed Wisconsin’s Goodwill Ambassadors for pointing out the state’s attractions!
The Ice Age Trail is an incredible national scenic trail that is largely unknown still – but not if I have anything to do with it 🙂 WI Goodwill Ambassadors would be a dream job for us! Maybe one day
nice towns, even one called Verona. I’ve been to Verona in Italy:)
Would you recommend Verona, Italy?!
Definitely. So much to see in Verona besides Juliet’s balcony. There’s Roman Arena, old castle, cute streets, river runs through the city center….lovely town
So good to hear! I will have to learn more about Verona. Thanks for putting it on our radar.