The #1 Chicago Road Trip Destination

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This is the 5th and final installment of unique and wonderful holiday weekend road trip destinations for Chicagoens. Each installment of this series has covered an unique and family friendly destination within driving distance from Chicago that offer hidden gems and delightful surprizes.

Make the 4th of July 2014 one that your family remembers forever with a visit to one of these family-friendly midwest hotspots. Each spot will be kid friendly and focus on needing little planning to enjoy.

If you plan to stay in a hotel, you can use priceline or one of those sites to find a cheap room nearby. If you want to camp, you will want to start calling nearby campgrounds ASAP as campgrounds fill up much quicker than hotel rooms.

Without further ado, here is the #1 road trip destination!

Top Five Chicago Road Trip Destinations: #1 Wisconsin’s Driftless Area

Unless you’re into fly fishing, you probably have not heard of the Wisconsin Driftless area. No, it has nothing to do with drifters. It is actually a natural geologic area that is strangely absent of the silt and other objects that the glaciers left behind as they receded. As a result, this area of Wisconsin looks like nowhere else in the Midwest. When you drive through this area, you will think that you somehow got transported to the Appalachian Mountains instead of western Wisconsin.

This area stretches from just west of Madison to slightly across the Mississippi into Minnesota, and down through north eastern Iowa and into portions of northern Illinois. The range of this area makes it an excellent choice for a “real” road trip weekend. You can begin your trip in IL, drive through Wisconsin and Minnesota and then visit Iowa on your way back home.

"M" is for Monadnock

The city of Baraboo has some pretty unique and interesting sights to see, like the circus museum and the Crane foundation, but the true wonder of this region is the state parks that are sprinkled around it. This region is home to wonderfully rugged and scenic state parks including Devil’s Lake and Wild Cat Mountain.

As you head farther west towards the Mississippi, Perrot State Park gives breathtaking views of the confluence of the Trempealeau and Mississippi rivers. It’s a hotspot for migrating birds, and prime eagle-spotting territory. It’s also home to Trempealeau Mountain, a 425-foot tall cone shaped monadnock surrounded by water. It looks almost surreal when you see it jutting sharply out of the water, and was considered to a sacred location by Native Americans.

Wisconsin's Driftless Area

Wisconsin’s Driftless Area

From La Crosse, you can follow the Great River Road south and enjoy the breath-taking scenery along the Mississippii River. This is a great spot to see bald eagles, hawks and other birds. When you get near Praire Du Chien, you can cross over into Iowa and visit the Effigy Mounds National Park. You can take a short hike to the look out point and see a view worth walking for. As you head further south in Iowa, you will have a hard time believing that you are, indeed, in Iowa.

A bit south of the National Park is the picturesque town of McGregor. This town looks like you stepped into the past, with historic signs and buildings. Spend a night in one of the quaint bed and breakfasts, and spend some time taking in the views and ambience of this beautifully preserved small town.

When you leave McGregor, stop by Pike’s Peak State Park. Unlike WI and MN state parks, Iowa does not charge enterence fees, so even a short stopover is worth it. If you only have a little bit of time, park near the visitor center and walk a short distance to the lookout point. Its less than 5 minutes from the parking lot and has an amazing view of the unique geography of this area.  From the top of the lookout point, you will be able to see the confluence of the Mississippii and Wisconsin Rivers, the bridge over the Mississippii in Marquette, and some of the most breath-taking views of Wisconsin that you will ever witness. It might not be quite like Colorado’s Pike’s Peak, but it is named after the same guy.

The view North from Pike's Peak

The view North from Pike’s Peak

From Pike’s Peak, you can follow the Great River Road south towards Dubuque IA as you head towards home. There are numerous small towns, lookout points and other activities to hit as you travel, so be sure to take your time as you menander back towards the IL border.Dubuque has some unique sites of its own, with historic buildings built on hills and bluffs that overlook the Mississippii. This postcard-perfect town also has unique rail cars that travel between the different elevations the city is on.

After Dubuque, you can cross back into IL and visit one of the most famous tourist areas outside of Chicagoland- Galena. Famous for being home to Ulysess S. Grant, this town combines stately historic homes with incredible views and vistas. There are numerous bed and breakfasts around the area, as well as campgrounds. Take time to wander down the streets of this historic town, and enjoy the feelings of a bygone era.

From Galena, you can follow 20 East through other small towns, but don’t forget to stop in Elizabeth, IL for some of the best ice cream you will ever taste at the Three Sisters Sweet Shop. Located right on rt. 20, this is a convenant stop that combines small town nostalgia with a delicious treat. The ice cream is fresh from Wisconsin and is pure, creamy goodness. The shop also sells excellent designer cupcakes that are worth every penny.

From Elizabeth, as you continue east towards home you will come across numerous other small towns with historic buildings and picturesque main streets. Don’t be afraid to stop often and stretch your legs- you will uncover hidden gems at each stop along the way home.

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