8 of the Best Midwest Road Trips

Looking to take a Midwest road trip? From Northern Michigan to major Midwestern cities, and everywhere in between, I've rounded up some of my favorite Midwestern locations you'll love!

Disclosure: some of the links below are affiliate links. If you purchase a linked item, I will make a commission, at no extra charge to you. As an Amazon Associate, I earn from qualifying purchases. Originally posted April, 2020.

Planning a Midwest road trip?

Now that the thought of travel planning is ever-so-slowly re-entering our minds, locations a little closer to home are at the top of the list, especially road trips! Without the hassle, expense, risk, and lack of social distancing inherent in airports, road trips are seeming like a friendlier option (someday!)

West Baden Resort, French Lick, IN

 As I dream about my own summer plans, I've compiled a list of the best Midwest road trips that I hope will be helpful, whenever you're able to hit the road and explore the world again!

Don't forget to check out my summer road trip essentials before your trip!

Midwest Road Trip: "Up North" Michigan

Sleeping Bear Dunes, Glen Arbor, Michigan

I thought I'd start off my list with a bang - my favorite spot in the Midwest, Northern Michigan.

From classy Petoskey, to historic and family-friendly Mackinac Island, and laid-back Traverse City and the Sleeping Bear Dunes, there's a city Up North to appeal to whatever kind of travelers you and your family are. Gorgeous lake-front views, quaint shops, water sports galore, this is Pure Michigan at its best.

If you want the best of all of the above, check out charming Glen Arbor and Leland, Michigan, just outside of Traverse City.

Midwest Road Trip: The Motor City: Detroit

Ah the Motor City. Full of history, and modern evidence of a recent rebirth, Detroit, and its surrounding communities, have a lot to offer.

Stop by Dearborn and visit the city's famed history museum/ park, The Henry Ford, home to all sorts of treasures, including entire homes moved from elsewhere. Feel the city's past and present heartbeat while you watch cars being made at Ford's Rouge Plant. Visit the Detroit Institute of Arts' impressive collection. 

Stay in the heart of the city's revived downtown, at the Shinola Hotel, or at my favorite spot, The Townsend in shopper's haven suburb Birmingham, where I once shared an elevator with the then-soon-to-be Speaker of the House.

Midwest Road Trip: Bloomington & French Lick

Moving south, consider exploring Southern Indiana, especially if you're coming from the surrounding states, it's incredibly accessible!

Bloomington

Consistently voted one of the best college towns in the US, Bloomington, home of Indiana University, bustles with life (and bars), year-round. Bloomington is particularly enjoyable in summer, when things are still open, but you'll have the run of the place.

Stay at the Indiana Memorial Union on campus, grab a fancy bite at Malibu Grill or FARM, and an after dinner college-style drink at Nick's English Hut or Kilroy's, if you're feeling young! Spend Saturday morning strolling Bloomington's "Rail Trail."

Sample Gates, Indiana University, Bloomington, IN

French Lick Resort

South of Bloomington is French Lick, the uniquely named Southern Indiana town that boomed around its (fragrant) hot springs, which drew visitors from all around. Revived by the owners of nearby Cook Medical at the turn of this century, French Lick Resort is a family-friendly resort, with two hotels, a casino, world-class golf courses, and a spa.

French Lick Resort

West Baden Resort Dome

Midwest Road Trip: Cincinnati

An easy road trip from our home base of Indianapolis, Cincinnati's Ohio River-side location offers plenty of entertainment for a weekend - and learning, as well.

Stop by the very well-done National Underground Railroad Freedom Center, visit the penguins at the Newport Aquarium, and grab a bite at the Hofbräuhaus.

Cincinnati has a 21c Museum Hotel - if you've never stayed at one, I highly recommend checking out the chain, which is a staple in many similarly sized Midwestern cities.

Midwest Road Trip: Louisville & The Bourbon Trail

Churchill Downs, Louisville

Is Louisville the south? Perhaps, but for my purposes, it's the Midwest! Head down to the home of the Kentucky Derby! Tour Churchill Downs and even explore the Bourbon Trail! Many of the distilleries, such as Evan Williams, actually have in-Louisville locations as well, if you don't have the time to tool around the countryside visiting the actual distilleries!

We loved our stay at the historic Seelbach Hotel, frequented by F. Scott Fitzgerald, and located in the heart of things in downtown Louisville.

Evan Williams, Louisville

Midwest Road Trip: Indianapolis

Be sure to consider a trip to the Circle City - Indianapolis! Home to the largest single-day sporting event in the world, the Indianapolis 500, when it welcomes almost 300,000 people to "The Track," Indianapolis continues to surprise visitors who come year after year.

Stop by Newfields, the world-class art museum and home to Robert Indiana's LOVE statue, the home of Benjamin Harrison (23rd president), and of course, the Indianapolis Motor Speedway. Discover Downtown Indy via the city's 8-mile bike path, the Indianapolis Cultural Trail!

Head up into the northern suburbs to explore Carmel's Arts and Design District and impressive Palladium, and Fishers' Conner Prairie Interactive History Park, much like a Colonial Williamsburg on the prairie. 

Explore Indianapolis's dining and bar scene, particularly Mass Ave and Fountain Square. Check out Sun King for local brews. Stay at The Conrad or Le Meridien, both boasting incredibly central locations.

Be sure to check out my Indianapolis Christmas activities, if you'll be visiting in winter!

Midwest Road Trip: Chicago

Chicago Water Tower

The largest city in the Midwest, Chicago is a rewarding road trip (and certainly worth a flight) from anywhere. Stay at our favorite hotel, The Drake, shop on Michigan Avenue, see a show, and visit the Chicago Art Institute. If you visit in the summer, take the train up to Wrigleyville and hit the bar scene before a Cubs game!

Midwest Road Trip: Lake Forest

Lake Forest, IL

This ritzy Chicago suburb deserves its own category. Lake Forest, one of the oldest and coolest of Chicago's suburbs, boasts streets of gorgeous houses, and an old, high-end downtown with great shopping.

Oh and did I mention the recently gutted, nearly 100-year-old Dear Path Inn? If you visit in the spring, you can visit their phenomenal showcase houses, as well.

At the Lake Forest Showcase House

Thanks for stopping by!

I hope you enjoy your Midwest road trip as much as we always do! It's my fabulous little corner of the world, so feel free to reach out in the comments if you have any questions - I've probably been there! xx And don't forget to subscribe to the blog newsletter, below!

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