By a Midwestern Mom Who’s Been There, Done That (and Packed the Snacks)
Oh my goodness, friends! Let me tell you about the absolute BEST fall road trip I’ve ever taken with my family. After 15 years of living in this beautiful heartland and dragging my kids (and reluctant husband) to every scenic overlook within a 500-mile radius, I’ve finally figured out the perfect autumn adventure. And honestly? It beats those crowded New England trips any day of the week!
Now, I know what you’re thinking – “But Karen, doesn’t everyone go to Vermont for fall colors?” Well, let me tell you something. Last October, my sister-in-law spent a fortune on a weekend in Vermont and came back with photos that looked exactly like what I captured right here in our backyard. The difference? I didn’t have to fight traffic for three hours just to find a parking spot, and I could actually afford to take the whole family without eating ramen for a month!
This journey I’m about to share with you has been my go-to recommendation for every mom in my book club, my neighbors, and basically anyone who’ll listen at Target. It’s doable, it’s gorgeous, and most importantly – it’s budget-friendly and kid-approved. So grab your favorite coffee mug (you know, the one that says “Mom Fuel”), and let me walk you through this amazing adventure from Wisconsin down to Missouri.
Planning Your Perfect Fall Road Trip: What I Wish Someone Had Told Me
Before I dive into all the gorgeous places you absolutely MUST visit, let me share some hard-earned wisdom from someone who’s made every possible mistake on family road trips. Trust me, I’ve been there – crying kids, forgotten snacks, and that one time we missed peak foliage by a whole week because I didn’t plan ahead!
Timing is Everything (and I Mean EVERYTHING!)
Oh honey, this is where I messed up royally my first time. I just assumed all the leaves would be pretty in October. Wrong! The colors start up north in late September and work their way south. I learned this the hard way when we showed up to Wisconsin in November and found bare trees. My kids still tease me about our “stick-watching” vacation!
Here’s what I do now (and it works like a charm):
- Check those online fall foliage trackers religiously – I bookmark at least three different ones
- Follow local park Facebook pages and Instagram accounts (#WisconsinFall is my favorite)
- Call the visitor centers about a week before we leave (those park rangers are absolute angels and know EXACTLY what’s happening)
- Build in some flexibility – sometimes you need to flip your itinerary if the colors are running early or late
Pro tip from this mama: I always plan for about 10 days total, which gives us wiggle room to chase the colors wherever they’re peaking!
Pack Like You’re Prepared for Four Seasons in One Day
Midwest fall weather is more unpredictable than my teenager’s mood swings! I’ve learned to pack like we’re going to experience everything from summer heat to winter frost – because we probably will.
My go-to packing list:
- Layers, layers, layers! (I pack hoodies for everyone, even if it’s 70 degrees when we leave)
- Waterproof jackets (because nothing ruins a hike faster than unexpected rain)
- Comfortable walking shoes AND waterproof boots (learned this one the hard way at Devil’s Lake)
- Extra socks (trust me on this one)
- Hand warmers for those chilly morning hikes
- A thermos for hot chocolate – this is NON-NEGOTIABLE with kids!
Photography Tips from Someone Who’s Taken 10,000 Fall Photos
I’m not a professional photographer, but I’ve definitely learned a few things about capturing these amazing colors:
- Get up early! I know, I know – nobody wants to wake up at 6 AM on vacation. But that morning light is absolute magic, and you’ll have the places to yourself.
- Don’t just take wide shots – get close-ups of individual leaves, bark textures, and water reflections
- Include people in your photos! My favorite shots are of my kids throwing leaves or my husband pretending to be annoyed (he secretly loves it)
- Take photos throughout the day – the colors look completely different in morning light versus afternoon sun
Beat the Crowds (A Survival Guide)
Listen, I love people, but I don’t love fighting crowds when I’m trying to enjoy nature with my family. Here’s what I’ve learned:
- Weekdays are golden if you can swing it (I know, I know – school schedules are rough)
- Early morning and late afternoon are your friends
- Pack a picnic lunch so you’re not competing for restaurant tables
- Research the “hidden gems” near popular spots – often just as beautiful with half the people
Road Trip Essentials (From a Mom Who’s Done This A LOT)
- Download offline maps (cell service can be spotty in these beautiful, remote areas)
- Pack a cooler with everyone’s favorite snacks (prevents 90% of car meltdowns)
- Bring activities for the car rides – audiobooks, games, whatever keeps your crew happy
- Keep a roadside emergency kit (because Murphy’s Law loves family vacations)
Okay, now that I’ve shared all my hard-learned lessons, let’s get to the good stuff – the absolutely stunning places that will make your heart sing!
Stop 1: Devil’s Lake State Park, Wisconsin
The Place That Made Me Fall in Love with Midwest Fall
Oh. My. Goodness. If I could only take you to one place for fall colors, this would be it! I still remember the first time I drove up to Devil’s Lake – I literally gasped and pulled over because I couldn’t believe something this beautiful existed just three hours from my house.
Picture this: these massive, ancient cliffs rising 500 feet straight up from the most gorgeous blue lake, and in fall, the whole thing is just wrapped in the most incredible colors. The maples turn this deep, rich red that looks like it’s on fire, the oaks go golden orange, and the birches add these perfect pops of yellow. It’s like someone took a giant paintbrush and went wild!
What Makes It Special
This isn’t just pretty – it’s dramatic. Those quartzite bluffs have been there for millions of years, and they create this incredible backdrop for all the fall colors. When you’re hiking up there, you feel like you’re on top of the world, looking down at this perfect little lake surrounded by forests that look like they’re glowing.
My kids (ages 8 and 12) absolutely love it here because it feels like an adventure. We’re not just walking through pretty trees – we’re climbing ancient rock formations and discovering hidden overlooks.
What We Always Do There
The Hiking: Now, I’m not going to lie – some of these trails are challenging. But don’t let that scare you off! The East Bluff Trail is the one everyone talks about, and yes, it’s steep, but the views at the top are worth every huff and puff. I always pack extra water and snacks, and we take our time. The Balanced Rock Trail is where I got my favorite family photo – my kids posing by this precarious rock with the lake and fall colors spread out behind them.
If you’re traveling with little ones or just want something more relaxed, the Steinke Basin Loop is perfect. It’s flat, easy, and still absolutely beautiful.
The Water Activities: We always bring our kayaks (you can rent them too), and paddling around the lake in fall is pure magic. The water is so calm and clear that you get perfect reflections of all the colorful trees. My husband, who usually grumbles about getting up early, admits this is his favorite part of the whole trip.
The Picnicking: I always pack a big lunch because there’s nothing better than eating surrounded by all this beauty. The South Shore has tables right by the water, and watching the light change on the cliffs while we eat is just perfect.
My Insider Tips
- Get there EARLY! I’m talking 8 AM at the latest, especially on weekends. The main parking lot fills up fast, and you do NOT want to be driving around looking for parking when you could be hiking.
- Bring layers: It can be 20 degrees cooler at the top of the bluffs, and that lake breeze is chilly in the morning.
- Stop at the visitor center first: The rangers are so helpful and can tell you which trails have the best colors that day.
- Stay in Baraboo: It’s a cute little town with great restaurants and reasonable hotels. The kids love the Circus World Museum if you need a rainy day activity.
When to go: Late September to mid-October is perfect, but check those color reports!
Stop 2: Starved Rock State Park, Illinois
Where Canyons Meet Fall Colors
After Devil’s Lake, you might think, “How can anything top that?” Well, let me tell you about Starved Rock! This place is completely different but equally stunning. Instead of big bluffs and a lake, you’ve got these incredible sandstone canyons that feel like you’re exploring a secret world.
I remember the first time we hiked into French Canyon – my daughter whispered, “Mom, this is like a fairy tale!” And she’s right. These narrow canyon walls covered in colorful leaves, with little waterfalls trickling down (if you’re lucky with the rain), create this magical, otherworldly feeling.
Why It’s Amazing
What makes Starved Rock special is how intimate it feels. Instead of big, sweeping vistas, you’re walking through these narrow canyons where the fall colors are right there around you. The sandstone walls create these cool, shady areas where the colors seem even more vibrant. And if there’s been recent rain, those seasonal waterfalls are absolutely gorgeous!
Our Favorite Things to Do
Canyon Hopping: We make it a game to visit as many canyons as possible. French Canyon is the most popular (and for good reason – it’s gorgeous), but St. Louis Canyon and Ottawa Canyon are equally beautiful and sometimes less crowded. Each one has its own personality and different types of trees, so the colors vary from canyon to canyon.
The Lodge: After a morning of hiking, we always stop at the historic Starved Rock Lodge. It’s this beautiful stone building from the 1930s, and sitting by their fireplace with hot chocolate after a chilly hike is pure bliss. The kids love exploring the lodge, and they have a decent restaurant too.
Illinois River Views: The boat tours are really nice if you want to see the park from a different perspective. The kids enjoy being on the water, and you get amazing views of the bluffs covered in fall colors.
What I Wish I’d Known
- Wear good shoes: These trails can be slippery, especially near the waterfalls. I learned this the hard way when my husband slipped on wet leaves (he was fine, but his pride was bruised).
- Bring a flashlight: Some of the canyons are pretty dark, and a little light helps you see the trail better.
- Check the waterfall status: The waterfalls aren’t always flowing, so call ahead if that’s important to you.
- Consider Matthiessen too: It’s just down the road and often less crowded with similar beautiful canyons.
Best time: Mid to late October is usually perfect.
Stop 3: Lake of the Ozarks State Park, Missouri
Where Water Meets Autumn Magic
By the time we get to Missouri, we’re really settling into vacation mode, and Lake of the Ozarks is the perfect place to relax and enjoy some of the most beautiful water-and-fall-color combinations you’ll ever see.
This lake is HUGE – like, so big you can’t see across it in many places – and it has this incredibly winding, complex shoreline that creates thousands of little coves and inlets. In fall, every single one of those coves is surrounded by trees in their autumn glory. It’s like driving through a painting!
Why We Love It
The thing about Lake of the Ozarks is that you can enjoy the fall colors so many different ways. You can drive the scenic roads and pull over at overlooks, you can hike through the forests, or you can get out on the water and be completely surrounded by the colors. It’s perfect for families because there’s something for everyone.
My kids love being able to swim (if it’s warm enough) and explore the shoreline, while my husband and I love the peaceful boat rides and the incredible photo opportunities.
What We Always Do
The Scenic Drives: Oh my goodness, the drives around this lake are incredible! Highway 5 has some amazing overlooks where you can see the lake stretching out with all these colorful hills rolling into the distance. We pack snacks and just spend a whole afternoon driving and stopping at viewpoints.
Boat Time: This is where the magic really happens. We rent a pontoon boat (it’s surprisingly affordable when you split it with another family), and we spend hours just cruising around, exploring different coves and inlets. The kids love jumping off the boat for a swim, and I love photographing the incredible reflections on the water.
Hiking in the State Park: The Lake Trail is gorgeous and not too challenging. It winds right along the shoreline, so you get constant views of the water and the colorful trees. The Honey Run Trail is more secluded and perfect if you want to feel like you’re deep in the forest.
Ha Ha Tonka State Park: This is a must-do side trip! It has this incredible castle ruin (yes, really – a castle in Missouri!) and a natural bridge, all surrounded by fall colors. The kids think it’s the coolest thing ever, and the hiking trails are beautiful.
My Pro Tips
- Book accommodations early: This area gets busy in fall, and the good places fill up fast.
- Bring sunscreen: Even in fall, the sun reflecting off the water is strong.
- Check water levels: They can vary, which might affect some boat launches.
- Try the local restaurants: The area has some great places to eat, many with lake views.
Perfect timing: Mid to late October is ideal.
Stop 4: Branson, Missouri
Where Entertainment Meets Nature
Now, I know what you’re thinking – “Branson? Isn’t that just shows and tourist stuff?” Well, yes, but it’s also surrounded by some of the most beautiful fall scenery you’ll ever see! And honestly, after several days of hiking and camping, my family loves having some entertainment options mixed in with our nature time.
Branson sits right in the heart of the Ozark Mountains, and in fall, those rolling hills are absolutely stunning. The whole area is covered in oak and hickory forests that turn these rich golds, deep reds, and warm browns. It’s like being wrapped in a cozy autumn blanket!
Why It Works for Families
Branson is perfect for families because you can have the best of both worlds. Spend your mornings hiking and enjoying the fall colors, then catch a show or visit an attraction in the afternoon. It’s especially great if you’re traveling with kids who might be getting a little tired of “just” hiking after several days.
What We Love to Do
The Scenic Drives: Highway 165 has this incredible scenic overlook where you can see Table Rock Lake surrounded by all these colorful hills. It’s one of those views that makes you just sit there and stare. The Ozark Mountain Highroad is another beautiful drive, especially in the early morning when the mist is rising from the valleys.
Silver Dollar City’s Harvest Festival: If you’re there in late September or October, this is SO worth it! They decorate the whole theme park with thousands of pumpkins and autumn decorations, and they have special fall activities. My kids absolutely love it, and it’s a fun way to celebrate the season.
The Railway: The Branson Scenic Railway is perfect for a relaxing afternoon. You sit back and let someone else do the driving while you enjoy the beautiful Ozark scenery. The kids love trains, and it’s a nice break from hiking.
Ruth and Paul Henning Conservation Area: This is where we go for our nature fix. The trails are beautiful and well-maintained, and the fall colors are incredible. It’s less crowded than some of the bigger parks, which is nice.
What I’ve Learned
- Book shows in advance: The popular ones sell out, especially during peak fall season.
- Plan for traffic: The roads can get congested, especially on weekends.
- Mix it up: Don’t try to do everything nature-focused or everything entertainment-focused. The combination is what makes Branson special.
Best time: Late October to early November is perfect.
Stop 5: Ozark National Scenic Riverways, Missouri
The Perfect Grand Finale
I saved the best for last! The Ozark National Scenic Riverways is absolutely magical in fall, and it’s the perfect way to end this amazing journey. This is where you can truly unplug and immerse yourself in nature’s autumn show.
The Current and Jacks Fork rivers are spring-fed, so they’re crystal clear and the perfect temperature for floating, even in fall. These rivers wind through some of the most beautiful, unspoiled forests you’ll ever see. In autumn, when all the trees along the riverbanks turn color, it’s like floating through a living painting.
Why It’s the Perfect Finale
After all the hiking and driving and exploring, there’s something so peaceful about floating down a gentle river, surrounded by fall colors, with nothing but the sound of water and birds. It’s the perfect way to decompress and really soak in (pun intended!) the beauty of the season.
My kids, who can be pretty energetic, always calm down and get almost meditative on these float trips. There’s something magical about being on the water, moving at the river’s pace, completely surrounded by nature.
Our Must-Do Activities
The Float Trip: This is THE experience here. We usually do the stretch from Akers Ferry to Pulltite on the Current River – it’s about 6 miles and takes 4-5 hours with stops. The outfitters provide everything (canoes, kayaks, paddles, life jackets) and shuttle service. Just bring snacks, water, and your camera!
Visit the Springs: Big Spring is incredible – it’s one of the largest single-outlet springs in the world, and the contrast between the brilliant blue water and the fall colors is stunning. Alley Spring with its historic red mill is so picturesque it almost doesn’t look real.
Camping: If you can swing it, camping here is amazing. Fall nights are perfect for campfires, and waking up to the sound of the river and the sight of colorful trees is pure magic. The kids love roasting marshmallows and telling stories around the fire.
My Essential Tips
- Book with outfitters in advance: They provide everything and know the rivers best.
- Dress in layers: It can be chilly in the morning and warm in the afternoon.
- Bring a waterproof bag: For your phone, snacks, and dry clothes.
- Don’t overpack: You’ll be in a canoe, so space is limited.
- Check the weather: The rivers can be affected by recent rain.
Perfect timing: Late October to early November is ideal.
Quick Reference: Your 5-Stop Fall Foliage Road Trip
For those of you who want to save this itinerary or share it with your travel buddies, here’s a quick reference list of all our stops:
Stop 1: Devil’s Lake State Park, Wisconsin
- Location: Near Baraboo, Wisconsin
- Best Time: Late September to mid-October
- Must-Do: East Bluff Trail hike, kayaking on the lake
- Stay: Baraboo (hotels, B&Bs)
- Pro Tip: Arrive by 8 AM on weekends to avoid crowds
Stop 2: Starved Rock State Park, Illinois
- Location: Oglesby, Illinois (about 90 minutes from Chicago)
- Best Time: Mid to late October
- Must-Do: French Canyon hike, visit historic lodge
- Stay: Starved Rock Lodge or nearby hotels
- Pro Tip: Wear waterproof shoes for canyon trails
Stop 3: Lake of the Ozarks State Park, Missouri
- Location: Kaiser, Missouri
- Best Time: Mid to late October
- Must-Do: Scenic drives, boat rental, Ha Ha Tonka State Park
- Stay: Lake area resorts, vacation rentals, or park camping
- Pro Tip: Book accommodations early for fall season
Stop 4: Branson, Missouri
- Location: Branson, Missouri (heart of the Ozarks)
- Best Time: Late October to early November
- Must-Do: Highway 165 Scenic Overlook, Silver Dollar City Harvest Festival
- Stay: Branson hotels, resorts, or vacation rentals
- Pro Tip: Mix nature activities with entertainment for best family experience
Stop 5: Ozark National Scenic Riverways, Missouri
- Location: Van Buren/Eminence, Missouri area
- Best Time: Late October to early November
- Must-Do: Float trip on Current River, visit Big Spring and Alley Spring
- Stay: Primitive camping or nearby lodges
- Pro Tip: Book float trips with outfitters in advance
Total Distance: Approximately 800 miles over 10 days Best Overall Timing: Late September through early November (follow the colors south!)
Final Thoughts from This Midwestern Mom
After doing this trip multiple times with my family, I can honestly say it’s become our favorite fall tradition. Yes, it takes some planning, and yes, there are moments when someone’s cranky or the weather doesn’t cooperate, but the memories we’ve made and the beauty we’ve experienced together are absolutely priceless.
The best part? Every single year, the colors are different. We’ve never had the exact same experience twice, which keeps it fresh and exciting. My kids, who are now 8 and 12, still get excited when I start planning our fall road trip, and my husband has stopped pretending he doesn’t enjoy it.
This journey through the Midwest’s fall colors has taught me so much about the incredible natural beauty we have right here in our backyard. You don’t need to travel across the country or spend a fortune to experience some of the most spectacular autumn scenery in America. Sometimes the best adventures are the ones that start from your own driveway.
So pack up your family, grab your camera, and get ready for an adventure that will fill your heart and your memory cards. The Midwest’s fall colors are waiting for you, and I promise – you won’t be disappointed!
Happy leaf-peeping, friends!
P.S. – If you take this trip, I’d love to see your photos! Feel free to tag us in your roadtrip images on X, Pinterest, Insta, or Youtube !
