Summertime Free Road Trip Plan - Midwestern Magic

I had the pleasure of living in Michigan for three years and thanks to all the great Michiganders I met along the way, I’ve got a perfect summertime free road trip plan for you! It starts in Chicago, IL – one of the best cities in the U.S. – meanders through Michigan and up to the tip of the "mitten" of the state and its crown-jewel: Mackinac Island. This is a fantastic summer trip as you get a little summer-in-the-city along with plenty of pretty country roads, historical sights, gardens, and a picture-postcard island with a Victorian flair to finish it off - just like a cherry on top of a sundae!


Michiganders have a habit of pointing at their hands when they are trying to describe where something is. I was utterly baffled by this at first. What did they mean their family is from a spot in the middle of their palm? Now, they’re pointing at their thumb and talking about a vacation they took last year! What’s going on here?

Once I got over my confusion (it didn’t take long – all I had to do was look at a map), I started taking notes and visiting everything I could. This free road trip plan is the product of all that hands-on (har,har – okay, I know it’s bad, but I couldn’t resist) research and all the helpful and kind people of Michigan and Illinois that I’ve met on the road (many have become lifelong friends).

This free road trip plan is five full days long, allowing a day of travel on each end of the journey – whether you fly/drive or drive from home depends on you. Make sure to check the Wrigley Field schedule – you will want to attend a Cubs game on one of the two days you’re in Chicago (buy your tickets ahead to be sure – even if you don’t usually watch baseball, you’ll find yourself having a wonderful time. This is an all-American experience you’ll never forget!)

Free Road Trip Plan – Day One
Chicago, IL
This city may always be in the shadow of its northeastern neighbor, New York City, but that just makes it work harder – making it cleaner, friendlier, and more approachable than NYC. Chicago is a great city to cut your "city-teeth" on if you’ve never been to a city before – it’s wonderful without being overwhelming.

Make sure to arrive either the night before your first day in this city or very early in the morning, you’ll have two full days here and they’ll be busy ones! Start by driving down the Magnificent Mile – a section of North Michigan Avenue between Wacker Drive and Oak Street. From your car you’ll see not only many glittering skyscrapers, but also the city’s famous Water Tower and Pumping Station, the Tribune Tower, the Michigan Avenue Bridge over the Chicago River, and Chicago’s most elite hotel: the Drake. This will give you a great feeling for the city and get you more comfortable with it.

Next step on day one of this free road trip plan is to park your car – you’re walking for a while, so put on your walking shoes. There’s nothing like seeing Grant Park up close: you can stroll around the beautiful Buckingham Fountain and take pictures and then head north to visit Millennium Park. Be sure to see both the "Bean" a.k.a. Cloud Gate, a huge bubble of reflective steel, and the Crown Fountain – a unique glass fountain containing LED screens showing faces of people who seem to be spurting the water that falls down the face of the glass. There are many other sights in this outstanding park including a huge band shell, a colonnade, and many beautiful gardens and flower beds.

Next, head out of the park and over to Gage Restaurant and Tavern for lunch – it’s close to the Art Institute (our next spot on day one of this free road trip plan) and the food/service/ambiance is outstanding. If you want to go with something cheaper and more casual, get something from one of the many vendors in the park or in front of the museum.

Spend the afternoon at the Art Institute of Chicago. This museum easily rivals the Metropolitan in New York – and I tell you this as a person who loves the MET. Some of the most famous paintings in the world are housed here including great works by Monet, Renoir, Cezanne, Van Gogh, and Gauguin to name a few. Top that off with any special shows that are passing through and you’ve got an afternoon of entertainment.

If you really hate art, you could go shopping on the Magnificent Mile or skip lunch in the park and head over to the River North section of the city for some real Chicago deep-dish pizza. If you go to the art museum, be sure to get some of this great road food (deep dish pizza) for dinner one of the nights you’re here.

A must-do tonight is to see a show. Chicago rivals NYC with a wide array of high quality Broadway productions to choose from. There’s also a vibrant comedy scene for those who love live comedy. If you love the Blues, drop those last two suggestions and head to one of the many outstanding Blues clubs in the area – Chicago is the Home of the Blues, after all!

Free Road Trip Plan – Day Two
Chicago, IL
Start Day Two of this free road trip plan by heading over to the John Hancock Center’s observation deck. You’ll get a spectacular bird’s eye view of the city from the 94th floor – it’s really breathtaking. Be sure to get the audio tour – that’s the only way to really appreciate the view and understand what you’re seeing.

Whether you like things under the sea, in the heavens, or excavated from the earth – there’s something for you at Museum Campus. The Shedd Aquarium has only recently been surpassed (by Georgia) as the largest in the world and it houses every kind of sea creature – from teeny-tiny starfish to giant sharks. The Adler Planetarium offers every kind of star-gazing experience you want – including antique instruments and a virtual-reality theatre. The Field Museum has a scary t-rex skeleton, artifacts from ancient Egypt, and tools used by early man. Pick one of these places to visit – you can’t possibly visit them all and still make it to the ball game!

Head to Wrigley Field for an afternoon game and get a true taste of this all-American sport. There’s enthusiastic audience participation from start to finish including a hearty rendition of "Take Me Out to the Ball Game", lots of stamping and clapping, and everyone helps themselves to plenty of hotdogs and beer. I’ve known people (who used to dismiss baseball) to get tears in their eyes when they talk about their experience at Wrigley Field. It’s one of those things that should be on your list of a lifetime if you’re American (and that’s why I’ve included it in this free road trip plan!).

There are tons of great sports bars and restaurants in the area surrounding the ball field, so you can go there for dinner, or head somewhere else that appeals. There are many outstanding restaurants in Chicago to choose from – so many, you couldn’t visit them in a month, so you’ll just have to pick one and go for it. My favorite is Charlie Trotter’s – I enjoyed one of the most fantastic meals of my life there. Don’t stay up too late – tomorrow’s a busy day!

Free Road Trip Plan – Day Three
Holland, MI and Grand Rapids, MI
On this day of this summertime free road trip plan we leave the great city of Chicago behind and head into Michigan. Although I’m a big fan of back roads, if you want to see the sights in both Holland and Grand Rapids today, you’re best off hitting the main arteries. Using the main highways that hug Lake Michigan (I-94 and I-196), you’ll get to Holland in 2 ½ hours – aim to leave no later than 8:30 am to reach Holland by 11:00 am.

Although Holland is most well-known for its tulip festival every April/early May, it’s still a treat to visit year-round thanks to Windmill Island municipal park. Here you’ll feel like you’ve been transported to Holland the country – there’s an antique working Dutch windmill, "De Zwaan", a museum that is an exact replica of a 14th century inn, a Dutch carousel and beautiful gardens. I don’t recommend paying to get into the Dutch village unless it’s tulip season (it’s mostly a shopping area the rest of the year).

Why go here? Unlike most of the U.S. melting-pot, Holland was occupied primarily by Dutch settlers until recently. This Dutch village is as authentic as you’re going to get in the U.S.! Have lunch here – there are many restaurants to choose from. A popular favorite is New Holland Brewing Company downtown for casual burgers and pizzas plus beer made on the premises by this micro-brewery (they have a great tour, too).

The next place to hit on day three of this free road trip plan is the Frederik Meijer Gardens and Sculpture Park in Grand Rapids. Take MI-21, then MI-11, then MI-44 for some local color. It will take you about an hour to get there, leaving a full afternoon to enjoy this 30-acre garden and sculpture park. The sculptures here are by the biggies – like Rodin and Henry Moore. Many of the sculptures are physically huge – the one of a horse is 24-feet high.

To top it off, you’ll also be seeing gorgeous orchids in a beautiful glass conservatory, a perfect replica of a farmstead planted with crops, and a fantastical children’s garden that includes a tree-house village.

In spite of bust-times in Detroit, Grand Rapids is skating along quite well as most businesses (healthcare for one) there are not associated with the auto industry. Many say that Grand Rapids has that small-town feel in spite of being a city – making it a perfect place to stay overnight due to many lodging and dining options. If you really don’t want to be in a city, nearby East Grand Rapids has a charming downtown and a sleepy burb feel.

Free Road Trip Plan – Day Four
Petoskey, MI and Mackinac City, MI
Plan to hit the road by 9:00 am this fourth morning of the free road trip plan to take in all the sights. Take US-131 all the way up. The route starts off fairly large and then dwindles to a narrower road. The Michigan countryside is beautiful – lots of rolling hills and farms everywhere. Don’t be surprised if you get stuck behind a tractor!

On this part of the trip you might get that spooky feeling I used to get whenever driving around Michigan. It’s that where-is-everybody feeling that, if combined with the catchy tune from Twilight Zone, can really freak you out. Don’t worry! Everyone’s on the coast! Just in time for lunch and before you get too spooked, 131 runs right into Petoskey, a charming small town on Little Traverse Bay.

This town is definitely worth a pit-stop, not only for the unreal looking water (some say it’s aqua-marine, others say teal), but also for the great downtown area – the 'Gaslight District" is filled with shops and old hotels like Stafford’s Perry Hotel. There are many restaurants to choose from for lunch and it’s a great downtown to explore. The best (in oh-so-humble opinion) restaurant is City Park Grill – love the wooden bar, friendly service, and delicious food!

Back on the road again, head northeast on Rt. 31 for lots of great views of the bay plus the many small lakes that dot the region. You’ll also be passing through small hamlets and by fields of wildflowers. Signs will point you to Mackinac City – not a real city, but more of a village.

Spend the afternoon of day four of this free road trip plan at Colonial Michilimackinac (say that three-times-fast – I dare you!). This old fort and historic village is a lot of fun for everyone in the family. While you won’t need to spend more than an hour in Holland’s Dutch area, this is an attraction worth spending 2-3 hours visiting (or more if you have kids).

You really get a feeling of traveling through time as they start you in the times of the Native Americans and lead you through the various stages of this area’s occupation (Indians, French trappers, Colonial settlers). The reenactments are very realistic and educational, and there are lots of buildings to explore. Stay overnight in Mackinac City and get ready to hit the big-time: Mackinac Island!

Free Road Trip Plan – Day Five
Mackinac Island, MI
Ask anyone from Michigan their favorite summertime destination, and they’ll probably say Mackinac Island (pronounced "Mackinaw"). This crown-jewel of Michigan is a step back in time to the Victorian era.

Mackinac Island

Ferries to the island depart every half hour to the island. If you’re planning on today being your last day of your trip, plan on staying overnight in Mackinac City rather than on the island as most hotels have a two-night minimum (depending on when you travel and where you want to stay). Alternatively, you can head over to the island after visiting Colonial Michilimackinac on the afternoon of day four of this free road trip plan. Then you could stay on the island at one of the many charming inns and hotels (if you can afford it, the Grand Hotel is a must).You’ll have to park your car in one of the parking lots though – no cars are allowed on the island.

Yes, you heard me right – you can only get around on bicycles, surreys or in a hired horse-and-buggy. They’re not kidding around about making it a true Victorian experience!

As you ride over on the ferry, pay some attention to Mackinac Bridge – not only is it beautiful, it’s also one of the world’s longest suspension bridges. Once you’re on the island there is plenty to do for the day including getting a buggy ride, exploring the charming downtown, visiting the awe-inspiring Grand Hotel (HUGE front porch lined with white painted rocking chairs) and chowing down on the island’s famous fudge.

Free Road Trip Plan – Final Notes
You can stay longer on Mackinac Island, of course. It depends completely on your schedule. If you’re looking for relaxation with a touch of history, this island is a joy. Most of the island is a state park, so if you stay longer, consider going on a hike. There’s also a yacht race every July. This island would be a fantasy on Fourth of July, if you can get a room.

On your way back, stop in Traverse City for some great food – especially Cousin Jenny’s for a real Michigan road food: pasties! This free road trip plan was designed for anyone, but especially for those who might sneer, “The Midwest? What’s to do there? It’s just a bunch of fields!” So not true! This road trip will give you a whole new appreciation for the mid-western section of the U.S.

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