Midwest Fall Road Trips

5 Fall Road Trips In The Midwest For The Best Fall Colors (2023)

Our Adventure Is Everywhere contains affiliate links and is a member of the Amazon Services LLC Affiliate Program. If you make a purchase using one of my Amazon or other affiliate links, I may receive compensation at no additional cost to you. Read my full privacy policy for more information.


5 Fall Road Trips In The Midwest

Since fall is on the way, now is the time to plan some fun fall road trips in the Midwest. Fall is prime leaf peeping time and the weather is gorgeous – not too hot and not cold yet.

All of these are fun road trips that I’ve embarked on in the past few years, and plan on repeating in the years to come too as I really think they are the best fall road trips in the Midwest.

1. Indianapolis to Nashville, IN

Map of Fall Midwest Road Trip Indianapolis to Nashville

Where To Stop During This Midwest Road Trip

Even though this trip doesn’t cover a lot of miles, there is plenty to do and see. Plus, your scenery changes dramatically the further south you head!

Start your trip just half an hour south of Indy in Frankin, IN. Try to time it so you can enjoy a movie at The Artcraft Theatre downtown. It’s beautifully restored in the art deco style and shows a variety of classic films. Enjoy an early dinner first at one of the many delicious choices within walking distance of the theater. I’d suggest either The Willard or Richard’s Brick Oven Pizza.

Artcraft theater in Franklin, IN

Early the next morning, stop at Ann’s Restaurant for a delicious homemade breakfast and then spend a little time shopping downtown. Franklin also has a beautiful college, perfect for a stroll to admire the changing leaves.

Looking for more things to do in Franklin? Check out these related posts: Friday Night Fun in Franklin, Goat Yoga and Downtown Franklin, Exploring & Enjoying Franklin

Head a bit further south to your final destination, Nashville, IN. Nashville is in Brown County and is the epicenter for beautiful fall foliage in Indiana. You’ll definitely want to spend some time hiking at Brown County State Park to fully enjoy the fall colors.

After a few hours of hiking, plan to stroll downtown Nashville, IN. The town is chock full of unique shops, art galleries, crafts, and more. You can easily spend an entire day exploring a few blocks – they are just so packed with interesting stores.

Enjoy Nashville, IN on your Fall Midwest Road Trip

Another fun place to visit in Nashville, IN is Hard Truth Hills. It’s a brewery, restaurant, distillery and more, and not only is the setting beautiful, but there is plenty to do to entertain you when you visit.

Looking for more information and things to do in Brown County? Check out Shopping and Sipping in Brown County, Indiana.

At least one day you should definitely head over to Columbus, IN to check out the architecture. Columbus is well-known for its world-class architecture.

Take a guided tour (or pick up a map at the visitors’ center) and admire the dozens of buildings and sculptures created by famous architects. It’s amazing how many lovely and interesting sites are located in this small Midwestern town.

The tours do book up quickly, so if you’d like to do one (and it’s by far the easiest way to see the highlights), be sure to book early.

Columbus also offers unique shops and several delicious local restaurants. A personal favorite is 450 North. With oven-fired pizzas, sandwiches, salads, and more you are in for a treat. Plus, there is a brewery and winery on site, AND they make ciders too! YUM!

If you have little kids, be sure to take them to The Commons and the Children’s Museum – both are right downtown and fun places for kids to learn and explore.

enjoy architecture in Columbus, IN on your Midwest Road Trip

Where To Stay During This Midwest Road Trip

For your first night in Franklin, IN, your best choice is the Fairfield Inn & Suites. It’s an affordable option for a pretty new hotel.

Since there is so much to do in both Nashville and Columbus you’ll want to spend at least two nights in the area. A few great choices would be either the Abe Martin Lodge at Brown County State Park (it’s recently been remodeled) or The Hotel Indigo in downtown Columbus – make your decision based upon which area you plan on spending the most time in!

Click Here To Book Your Stay At The Hotel Indigo Today

2. Chicago to Starved Rock State Park

Chicago to Starved Rock State Park

Less than a hundred miles southwest of Chicago is perhaps my favorite state park for hiking. Starved Rock State Park has 13 miles of gorgeous trails – especially in the fall when the leaves are turning.

Where to Stop During This Midwest Road Trip

The hiking at Starved Rock leads you to beautiful ravines, lovely waterfalls, and all kinds of interesting terrain. It’s truly a hikers’ paradise, and most of the trails are easy to moderate so the whole family can enjoy them!

starved rock state park is a great place to see fall foilage on your next Midwest Road Trip

After spending a day hiking and enjoying the fall foliage, head over to the nearby town of Ottawa for a delicious dinner at one of the local restaurants, and then head over to The Lone Buffalo for a flight of local beer. They often have fun events going on like trivia or live music, so time your visit accordingly if you can.

Early the next morning, fuel up at Jeremiah Joe for a delicious coffee or tea and a bite to eat before heading back out to enjoy the fall colors – this time at Matthiessen State Park. Matthiessen has some gorgeous rock formations and the hiking is perfect!

Enjoy coffee at Jeremiah Joe in Ottawa, IL

A few other fun potential activities include fall color trolley tours and river cruises from Starved Rock State Park. You’ll also find several adorable shops for browsing in downtown Ottawa. On our last visit, I picked up a unique, homemade metal house decoration.

Where To Stay During This Midwest Road Trip

If you enjoy a rustic feel as well as being right in the middle of the fall colors, you can stay at the Starved Rock Lodge. There are two types of rooms available – those in the Lodge Wing, which are built in the 1930s and part of the original lodge, or the rooms in the hotel wing. The hotel wing rooms still feel historic but are a bit newer and larger.

A more modern choice would be the Holiday Inn Express & Suites in Ottawa, IL. Nicely situated in Ottawa, it’s an easy drive to both parks, and all the shops and restaurants downtown.

Click Here To Book Your Stay At The Holiday Inn Express & Suites Today

3. Milwaukee to Lake Geneva

Milwaukee to Lake Geneva

Lake Geneva is a short drive from Milwaukee and a wonderful spot to enjoy fall colors in Wisconsin. It’s also pretty close to Chicago if that’s an easier starting point!

Where to Stop During this Midwest Road Trip

By mid-October, the leaves in Lake Geneva are really popping, and when you drive around to admire them, you’ll also get to see some of the truly jaw-dropping mansions built in the 1800s by Chicago’s elite. They were used as vacation getaways by many prominent Chicago families.

To really get the full effect of the fall foliage, rent a bike and spend an afternoon biking around the lake on the paved bike paths, or enjoy walking on part of the 21-mile Geneva Lake Shore Path – you’ll go right by many of the mammoth mansions as well as perfect views of the lake.

Spend at least one afternoon zipping through the trees at Lake Geneva Ziplines & Adventures. You can choose to zipline, hike, enjoy the high ropes excursion, or all of the above! It’s a thrilling way to get outside and enjoy a fun fall day.

The town of Lake Geneva is darling, with boutiques, local restaurants, and more. Plus, there are several nearby wineries, breweries, and even a distillery so you could have a fun day creating your own winery tour!

Where to Stay During this Midwest Road Trip

You can’t go wrong by staying at the Geneva Inn. The Inn is located directly on Lake Geneva with breathtaking views from many of the rooms. Even if you don’t stay there, consider enjoying a decadent weekend brunch at the connected restaurant.

Click Here To Book Your Stay At the Geneva Inn Today

4. Cincinnati, OH to Evansville, IN

Cincy to Evansville

This Fall Midwest Road Trip includes a large section of the Ohio River Scenic Byway and takes you through quite a few charming river towns as well as several larger Midwestern cities. To really enjoy this Fall Midwest Road Trip, allow yourself at least 5 nights so you can take your time exploring the region.

Where to Stop During this Midwest Road Trip

By starting your trip in Cincinnati, OH, you’ll get to your first destination, Madison, IN in just about an hour, but leave early so you can spend a full day exploring Madison’s charms.

Downtown Madison is chock full of unique shops and restaurants, so grab a coffee at the local coffee shop and start exploring. After lunch downtown, head over to Clifty Falls State Park for a bit of hiking and leaf peeping.

Your next few days will be spent exploring the towns of Jeffersonville, IN, Clarksville, IN, New Albany, IN, and Louisville, KY. Give yourself at least three days to get a good taste of this region, and be sure to include some bourbon tastings in Louisville, a day at the Louisville Slugger Museum, and a visit to the Kentucky Derby Museum at Churchill Downs, the home of the Kentucky Derby. Louisville is also home to several amazing local coffee shops – Please & Thank You is a local favorite!

You'll definitely want to enjoy local coffee shops on your Midwest Road Trip!

The Culbertson Mansion in New Albany and the Howard Steamboat Museum in Jeffersonville should also be on your list of things to see. All along the riverfront, you’ll get to enjoy fall colors, and a fun way to get a unique view is to walk across the Big Four Bridge.

Head out of this area and you’ll quickly come to Corydon, IN. Although not on the river, it’s part of the Ohio River Scenic Byway and another city worth exploring. Corydon was the first Indiana capitol so there is quite a bit of history right downtown. Check out historic sites such as the Corydon Capitol State Historic site, the Constitution Elm, and the William Henry Harrison log cabin.

Spend a night here in Corydon and then finish your road trip by driving to Evansville, IN the next day.

You won’t run out of things to do in Evansville. To get the most fall foliage time, I’d start with a visit to Angel Mounds to do a little walking outside (but also be sure to check out the museum onsite). Mesker Park Zoo & Botanic Garden would be another lovely outdoor choice.

Evansville boasts several museums worth spending time in, especially if the weather isn’t ideal for being outside. There is even a casino if you want to do a little gambling!

Where to Stay During this Midwest Road Trip

Plan a night in Madison, two nights in Louisville, a night in Corydon, and one in Evansville. If you want to extend this trip a bit longer you could add another night in Louisville and Evansville and easily keep busy.

Click Here To Use Booking.com to Book Your Stay Along the Ohio River Scenic Byway Today

5. Michigan Tunnel of Trees

Although the Tunnel of Trees begins and ends in Harbor Springs, Michigan, there are actually quite a few small towns nearby that can help you make up a lovely Fall Midwest Road Trip to enjoy plenty of fall colors!

Where to Stop During this Midwest Road Trip

You’ll definitely want to spend a morning or afternoon driving the Tunnel of Trees. It’s gorgeous any time of the year, but especially breathtaking in the fall when the leaves are in full color. If you can plan it during the height of the season you’ll enjoy a site you won’t soon forget.

After you’ve had your fill of fall foliage, plan to spend a few days exploring the rest of the region. Harbor Springs, Bay Harbor, Petoskey, Charlevoix, and Boyne City are all wonderful towns with all kinds of interesting things to do.

Enjoy a local restaurant in Boyne City on your Fall Midwest Road Trip

A few options include renting kayaks and getting out on the water at Petoskey State Park, looking for Petoskey stones around any of the lakes in the region, shopping at the quaint shops and boutiques in any of the towns, and enjoying local restaurants.

Looking for more things to do in Petoskey and Boyne City? Check out these related posts: A fun family day in Petoskey, MI, and The BEST Boyne City Restaurants

Definitely plan on visiting a few of the wineries and farm markets in the region. You can stock up on local wines and produce as well as spend time outside. Another fun experience is to check out the mushroom houses in Charlevoix – they are definitely unique!

Although Boyne Mountain is often thought of as a winter destination (thanks to the ski slopes), it’s actually a wonderful spot to visit year-round. In the fall you can have fun hiking, ziplining, playing golf, and mountain biking, so be sure to add those activities to your trip.

Boyne Mountain is fun in the fall too.

Where to Stay During this Midwest Road Trip

Petoskey is a fantastic choice as a base for your explorations. My favorite hotel in Petoskey is the Holiday Inn Express & Suites. If you can, request a lake view room for fantastic views of the lake. It’s also perfectly located for spending time in each of the towns nearby.

Click Here To Book Your Stay At the Holiday Inn Express & Suites in Petoskey

Conclusion: 5 Fall Road Trips In The Midwest For The Best Fall Colors (2022)

Although exploring the Midwest is fun any time of the year, there is something super special about the fall. Depending upon the trip you choose, you’ll want to plan your trip sometime between mid-September and mid-October.

The leaves tend to turn earlier the farther north you are so if you get really ambitious you could potentially fit two or three of these road trips into a single season!


Planning on a fall road trip? Check out one of these 5 to find the BEST fall colors in the Midwest. #getaways #fallcolors #roadtrips
Planning on a fall road trip? Check out one of these 5 to find the BEST fall colors in the Midwest. #getaways #fallcolors #roadtrips