Welcome to the start of our brand-new blog series on our 2-Year North America Road Trip, 2015-2016. This journey was the grand finale of our five-year nomadic adventure, and it came at a time of massive growth for my blog, the end of my marriage, and the start of a whole new chapter for Mia, Caius, and me.
This wasn’t just any road trip – it was the road trip to end all road trips, packed with family adventures, laughter, epic discoveries, and unforgettable moments across the US and Eastern Canada.
We’ve road-tripped in Ireland, Wales, Bulgaria, the Mediterranean, Turkiye, and Australia, but nothing compares to the sheer scale and adventure of this family odyssey across North America.
We’ve taken plenty of road trips before and after this adventure, but this series focuses on our biggest and most unforgettable journey across North America in 2015–2016. During this time, we explored 48 US states and 7 Canadian provinces, creating what we consider some of the best USA road trips for families. To make it easy to follow, we’ve broken the journey into 12 phases, each covering a different region and experience.
- Eastern Canada Road Trip
- Midwest USA Road Trip
- Pacific Northwest USA Road Trip
- Western Canada Road Trip
- North Coast-To-Coast USA Road Trip
- Northeast to Southeast USA Road Trip
- Southeast to South USA Road Trip
- Grand Circle Road Trip (Part I)
- Grand Circle Road Trip (Part II – RV Adventure)
- California Road Trip – Sacramento to San Francisco (6 Days)
- Nova Scotia Road Trip (2 Weeks)
- Florida Road Trip Finale
We hope you’ll join us for every phase, sharing in the adventures, the chaos, the fun, and all the memories that make this family road trip truly unforgettable.
Phase 2 – Midwest USA
Indiana > Kentucky > Illinois
8th August – 26th AugustTotal approximate miles: 678 miles (1,091 kilometres)
Total fuel: US$68
Phase 2 of our North America road trip took us on vacations in the Midwest USA. After exploring the East Coast of Canada and completing our Eastern Canada road trips, we swapped coastal charm for classic Americana, quirky attractions, and some seriously fun family vacation experiences.
This part of our family road trip was shorter but packed with highlights, from theme parks and museums to unexpected stops that made this road trip with kids one to remember. Think meeting Santa Claus in August, exploring the world’s largest children’s museum, and diving into small-town USA charm.
Check USA Hotel Prices Here
Best Things To Do in Midwest USA
Fort Wayne, Indiana – Family Fun and First Stops
Dates: 8th – 11th August
Accommodation: Hilton Fort Wayne
Best Attraction / Tour: Fort Wayne Children’s Zoo
After dropping off our rental car, we spent a few days exploring Fort Wayne. The highlight for Mia and Caius was the children’s zoo, which honestly surprised me with how good it was.
We also squeezed in a theatre production of Mary Poppins, explored our ancestry, met the founder of Vera Bradley, and ate our way through the local food scene before jumping on a coach to Bloomington.
Bloomington, Indiana – Conference Life Meets Family Travel
Dates: 11th – 14th August
Accommodation: Marriott Courtyard
Best Attraction / Tour: 3 Day Indy Attraction – Indianapolis Zoo – White River State Park – Children’s Museum
We arrived in Bloomington for a travel conference, so while I was busy, Mia and Caius slowed things down. They explored, swam in the hotel pool, and had some much-needed downtime after the fast pace of our travels. It was a nice reset in the middle of our USA road trip.
Dubois County, Indiana – Small Town Midwest Charm
Dates: 14th – 15th August
Accommodation: Hampton Inn
Best Attraction / Tour: Scenic train ride and local food experiences
After the conference, we joined a group tour through Dubois County. We climbed aboard old trains, watched cornmeal being made, and ate some of the best comfort food in the Midwest.
This was one of those unexpected stops filled with outdoor adventures that make a road trip across North America so memorable.
Spencer County, Indiana – Santa Claus and Theme Parks
Dates: 15th – 17th August
Accommodation: Santa’s Lodge
Best Attraction / Tour: Holiday World Theme Park
Yes, we visited Santa Claus… in August. Now that’s a family adventure! Only in the USA. Spencer County is home to Holiday World, a giant theme park and one of the most fun, kid-friendly stops of our trip. Mia and Caius were in their element, and I loved seeing their excitement. We also explored Abraham Lincoln’s childhood home, adding a bit of history to the adventure.
Louisville, Kentucky – Iconic USA Experiences
Dates: 17th – 21st August
Accommodation: Galt House
Best Attraction / Tour: Louisville Slugger Museum & Factory
From Spencer County, we made our way to Louisville, where our group tour wrapped up. We picked up another hire car and settled in for a few days, gathering Midwest road trip ideas coming up.
Louisville is full of iconic experiences, from the Kentucky Derby to Muhammad Ali’s legacy. The standout for us was the Louisville Slugger factory, where baseball bats are made. It’s one of those uniquely American experiences that really brings a USA road trip to life.
Read all about what to do in Louisville with kids here.
Indianapolis, Indiana – The Ultimate Kid Stop
Dates: 21st August
Accommodation: Day stop
Best Attraction / Tour: Children’s Museum of Indianapolis
On our drive from Louisville to Chicago, we passed through Indianapolis, home to the world’s largest children’s museum. There was no way we were skipping that.
We spent hours running after Mia and Caius, exploring exhibits and letting them lead the way. If you’re planning a road trip with kids, this stop is an absolute must.
Chicago, Illinois – Big City Energy
Dates: 21st – 26th August
Accommodation: Friend’s house
Best Attraction / Tour: Willis Tower Skydeck
Chicago completely surprised me, in the best way. There is so much to do, and we barely stopped. We went to a Red Sox baseball game, did a pizza tour, had breakfast at the top of the Willis Tower, explored outdoor activities at Navy Pier, and even squeezed in some stand-up comedy.
Five nights weren’t enough. Not even close. Check out 15 things to do with kids in Chicago here.
On our final day, we slowed things down, packed up, and faced the reality of two months on the road. We had collected far too much along the way and had to let some things go before our flight.
That evening, we flew out of Chicago, stopped briefly in Salt Lake City, and arrived late in Portland, Oregon.
Wrapping Up Phase 2 of Our North America Road Trip
Phase 2 of our family road trips across North America delivered big on fun, especially for the kids. From theme parks to museums and everything in between, the Midwest USA proved to be full of surprises.
Next up, we head into one of my favourite regions in the world – the Pacific Coast Highway.
👉 Read Phase 3 – the best road trips – Pacific Northwest, USA
👉 Or head back to Phase 1 – Eastern Canada Road Trip
Top Tips for Families on a Midwest Road Trips
- Balance Big Cities with Small Towns
The mix of places like Chicago and Dubois County kept things interesting for both the kids and me, making this the ultimate family road trip. - Prioritise Kid-Friendly Stops
Theme parks and museums made this phase unforgettable. Always include stops that let kids burn energy. - Embrace the Unexpected
Santa Claus in August? Only in the Midwest. These quirky moments are what make a family gap year blog worth reading. - Plan Driving Days Around Experiences
Breaking up long drives with stops like Indianapolis made the journey just as fun as the destinations. Best family road trips should all do this. - Pack Smart for Short Stays
With lots of one-night stops, having a grab-and-go bag made life much easier during road trips in the Midwest.
Midwest USA Road Trip Itinerary – Phase 2 Overview
If you’re planning a Midwest USA road trip as part of a bigger North America road trip, this road trip guide is short, easy to follow, and packed with family-friendly stops. It’s perfect for a road trip with kids and fits beautifully into a longer USA road trip or family gap year blog itinerary.
Route Overview:
Fort Wayne, Indiana → Bloomington, Indiana → Dubois County, Indiana → Spencer County, Indiana → Louisville, Kentucky → Indianapolis, Indiana → Chicago, Illinois
Duration: 18 days
Highlights of this Midwest USA road trip:
- Fort Wayne Children’s Zoo, one of the best kid-friendly stops in Indiana
- Holiday World in Santa Claus, Indiana, a must for any family road trip
- Louisville Slugger Museum, an iconic USA experience
- Children’s Museum of Indianapolis, the largest in the world
- Chicago’s top attractions, including Willis Tower, Navy Pier, and a classic pizza tour
Why this route works for families:
This stretch of the USA road trip is manageable, diverse, and full of interactive experiences. It mixes education, fun, and downtime, which is exactly what you need on a long-term road trip across North America.
Binge More Of Our 2-Year North America Road Trip Adventure
Loved Phase 2? Don’t stop now. Follow along with the rest of our epic North America family adventure:
