Roadtrip! Discover 5 Vacation Worthy Towns in the Midwest

The car is gassed up. You have your Kwik Trip snack of choice. Our family is all about the white cheddar cheese puffs and gummies, if you must know. You’ve got your playlist on the Bluetooth and the kids are already nodding off in the back seat. Is there anything better than a Midwestern road trip? Now that you’ve been transported to the driver’s seat in your mind, you need a destination. Once you discover these Midwest towns, you don’t have to go far to find destinations that will be fun all year round.

Mineral Point, Wisconsin

Do you want to step into the set of a Hallmark movie? If so, this Midwestern town nestled between the rolling hills of the Driftless Region and the hustle and bustle of Madison, WI, and the Chicago Metro area might be calling your name. The downtown strip is tiny, but it’s chock-full of charm. The historic buildings have a distinct Old World flair. Their stone facades are set against a rolling hill, giving you pretty, Insta-worthy views as you stroll through town. Stop at coffee houses, art galleries, and the cheese shop during the day. Visit the American Wine Project’s tasting room on weekend afternoons and evenings.

Mineral Point also has charming events throughout the year. Here are a few you might want to try to shoot for while planning your next vacation:

• Concerts and movies at The Historic Opera House
• 4th of July: The lineup includes an adorable parade, lunch accompanied by live music in the park, and an amazing fireworks display on the Main Street of their downtown.
• The Ice Lantern Fest: An annual event set in February, visitors can walk the downtown district and take in a street lined with ice lanterns. The festival also includes public fire pits, cake walks, and costume contests for all ages.

Galena, Illinois

This might be the Midwestern headquarters for girls’ trips. When my sisters and I went here, we scoured every shop for a “Gals in Galena” shirt to no avail. Still, we had plenty of fun. We took a ghost tour that included a delicious cocktail at each stop. We didn’t get scared… until we passed the old courthouse after dark and started to think about the stories the tour guide told us about. This town is also on a steep hill and has charming staircases studded throughout for beautiful views and photo ops.

Galena is split by the Galena River and offers two pedestrian bridges to give visitors access to the Galena River Trail and a variety of Civil War-era attractions. There’s plenty of fine dining to choose from, but if you’re visiting on a weekend, be aware that this is a popular destination. You may have to make a reservation at your restaurant of choice. Want to get a taste of the Driftless area countryside? Take a tour of a local farm, the kids might be interested in feeding some baby cows before sampling fresh ice cream.

Galena Festivals

• Great Galena Balloon Race and Festival: Occurring in late June, this event only costs 5 dollars to attend. Go early and listen to live music. Stay late and watch the Hot Air Balloon Nightglow. This event will become a core memory for people of all ages. Just be sure to bring cash as this event doesn’t accept credit cards.
• The Market House Square Art Festival: Occurring in mid-August, this free festival showcases area artists and food trucks, making it a delightful outdoor event that’s fun for the whole family.
• Halloween Parade & Festival: It makes sense that a town with three different ghost tours has one of the longest Halloween parades in the tri-state area. A food festival precedes the main event, so you can go for the whole day and delight in the spooky celebrations.

Grand Haven, Michigan

The white sands of Lake Michigan beaches, historic downtown charm, and an Insta-friendly lighthouse pier that will perfectly suit your fisherman-core needs. What else could a visitor looking for a midwestern beach vacation look for?

Grand Haven has plenty of things to do for all ages:

• Walk the picturesque pier: Take in two brilliant red lighthouses connected by a dramatic, towering walkway, which, as far as I can tell, is not open to the public. While most people visit in the height of summer, this site is worth visiting all year round, as Lake Michigan freezes into breathtaking ice sculptures when the temperature dips below zero.
• Rent a cycleboat: This looks like a lot of fun if you’re going on a vacation with friends. The boats can hold up to 16 passengers, all of whom must be over 18 years old. The outing functions like a Peddle Pub but won’t hold up traffic.
• Hop on the Lakeshore Trolley: Costing less than two dollars for a day pass, this hop-on on hop-off bus will take you to popular areas of interest throughout town. I know that my kiddo would love to take a ride on this old-school trolley, which is nice because kids under 4 ride free.
• Check out the Miniatures Museum: Who doesn’t love realistic figurines made tiny? If you’re visiting Grand Haven on a rainy day, this could be a cozy experience that you’ll never forget.
• Explore the many sand dunes: Many different sand dune areas are great for hiking and bird watching throughout the year. You can even go cross-country skiing at the North Ottawa Sand Dunes in the depths of winter.

The Amana Colonies

This is not your typical Midwest town. The Amana Colonies used to be a self-sustaining set of villages. In fact, the society maintained a communal way of life up until the 1930s. Now, it’s a unique historical site with plenty of activities to keep visitors occupied for a weekend. A walk down the main street, alone, is an enlightening experience. Lined with flowers and studded with a range of shops, including a meat and cheese shop, a toy store, and a textile store, there’s plenty to look at for everyone in the family. Once you’re done shopping, vacationers can enjoy the Fireside Winery that’s right in the village or play a round of golf among the rolling hills of The Amana Colonies golf course.

Staying Overnight

When I was there, I wanted to come back and stay overnight, and for good reason. There are so many cute places to stay, right in town, so you can immerse yourself in historic charm for a whole weekend. Hotel Millwright is a renovated textile mill right off the edge of the main drag. They don’t just pay tribute to their past, Iowa’s only remaining textile mill is located right on their campus. Though the amenities seem modern and comfortable, staying here seems like a great way to feel transported to a completely different era and place.

Cycling Through The Colonies

Of course, like any good Iowa tourist hub, the Amana Colonies boasts some nice biking trails and routes. Take the paved 21 mile Amana Trail in a loop from Amana and see more villages or do the family-friendly 3 mile Kolonieweg trail. Adventurous cyclists might want to check out the gravel routes that take off from West Amana. The map shows out and back routes but I’m sure intrepid gravel cyclists could find a way to make it a circuit if they put their minds to it.

Amana Festivals

• Wurst Fest: This totally tubular festival takes place in June and I’m starting my campaign to comvince my family to come with me as of right now. What do I find delightful about this festival? Let’s see… yes, I love their tag line: “Come have the wurst time”. Yes, I love the idea of sampling artisanal sausages all day long. But let’s be honest, the biggest draw to this festival has to be the Dashhund Derby featuring six different categories of weiner dog racers.
• Iowa’s Rennaisance Faire: Taking place in May and October in Middle Amana, this event gives history lovers a great excuse to visit the area while also downing their very own turkey leg.
• Oktoberfest: Can you run a German colony without also hosting one of the biggest Oktoberfests in the state? I think not. This festival has been running for over 60 years. Visitors can take in top-notch polka music, eat mountains of German food, and let their kiddos run loose at the Kinderplatz.

Winona, Minnesota

Okay, I’ll admit it. This is my hometown. But after taking it for granted for 18 years, then coming back without the time to do everything I while visiting, I’m sure this Mississippi town would make a great getaway for any Midwestern road (or train!) tripper. Winona is right on the Amtrak line. Anyone from the Twin Cities or Chicago can visit this spot without facing any time on the highway.

A Day Downtown

The big river reigns supreme in Winona, Minnesota. The Midwestern town boasts one of the only remaining boat house colonies. The Levy Park is rich with gardens while the sorrounding downtown has plenty to offer in the way of dining and entertainment.

Start your day off with a Bloedows (pronounced Blae-dows) donut. Their specialty is the maple long john but you really can’t go wrong with anything on display. They haven’t changed most of the recipes in decades. Get there early. This establishment has been open since the twenties but it’s been very popular in the last few years. Latecomers may have to join the cue that’s wraps around the corner and down the street.

After you’ve got your greasy white box full of fried treats, go to The Blue Heron Coffeehouse for a latte. Now, bring that heavenly combination to Levy Park for a picnic. Challenge the family to a little climbing on the newly installed bouldering rock while you digest. After this, take a tour on the Winona Tour Boat, for an upclose look at The Great Mississip.

Okay, it’s already been a day but you don’t even need to leave the area to keep the fun going. Check out Two Fathoms Brewery for delicious local beer. You may even be able to catch some local music here. If you can’t find music there, check the line up at Ed’s No Name Bar. While it’s not as family friendly, they often have top tier artists play in the evening.

Winona’s Historic Attractions

Ready to head inside for some culture? Do a little self-guided tour of town and check out these historic buildings. The buildings listed are all within a four block radius:

• The Winona County History Center: Let your kiddos explore a model paddle boat, a teepee, and a cave.
• Winona National Bank: This is a working bank that keeps regular business hours. Here’s your insider scoop. go upstairs for a bird’s eye view of the stunning early 20th century architecture. There, you’ll also get to see a collection of taxidermied exotic animals from the turn of the last century. Growing up, I refered to this gorgeous structure as the “dead animal bank”.
• The Winona Library: A beauty from the outside, the real architural eyeful resides on the second floor of this library. Head through the computer room and into the reading room to see the stunning stained glass dome. Don’t stop there. Explore the stacks and take in the cast iron shelves set into the thick, milky glass flooring. Just remember, it’s a working library so keep your gasps of wonder to a whisper.

Winona Festivals

• Mid West Music Fest: An annual spring music festival with venues set throughout the city, this event brings in artists of all genres from around the midwest.
• The MN Beethoven Festival: Happening in consecutive weekends in early summer, the Beethoven festival is a great way to take in top notch music on a dime. There’s even an annual free Minnesota Orchestra concert at the Lake Park Bandshell.
• Boats and Bluegrass: Boats and… Bluegrass! This three day music festival in September takes place at Prairie Island and showcases bluegrasses musicians from all over the world. The grounds feature hand painted decorations and classic Winona performers… looking at you, Doctor Bob. While it’s not cheap to attend, this event is great for families. The grand stage frames the river bluffs, capturing the hills as they just begin to change during the first weeks of fall. The festival also offers free canoing, kayaking, and paddleboarding with a tickey so attendees can get their fill of art and nature in one weekend.

Start Planning Your Next Roadtrip

So there you have it. If you’re a Midwesterner, longing to get into your car and out of your routine, these Midwestern towns will make your three-day weekend memorable. Treat yourself and start planning your next trip, today! Want to know more about these locations? You can bet I was forced to leave plenty out. Leave your questions in the comment section and I’ll be happy to answer them! If you’re looking to stay even closer to home, check out these Midwestern Staycation trips. Just because you’re out of PTO, doesn’t mean your weekends have to be a wash.