I-90 to Seattle

As you head out of Chicago, visit Legoland Discovery Center in Schaumurg, IL. There are over 3 million lego bricks here and you can easily spend the day exploring with kids. Keep in mind that Legoland is a kids attraction, and all adults must be accompanied by a child. If you happen to have a kid around, though, it's a can't-miss stop!

If you're road tripping during summer and fall, you'll absolutely want to visit Goebbert's Pumpkin Patch in Pingree Grove. There's so much to do, especially during autumn, from a pumpkin-eating dinosaur, to a hay bale maze, and basically every other fall-themed outdoor activity you can think of. Oh, and the puppet show is absolutely adorable.

TIP: Go during the week to avoid the massive weekend fall crowds. And don't forget to stop at the cafe and gift shop!

I-90 then makes its way into Wisconsin! Lake Kegonsa State Park is considered "one of the best-kept secrets of southern Wisconsin." This state park features a 3,200-acre lake, woodlands, a swimming beach, fishing, a boat launch and campground. There are tons of hiking trails and picnic places in case you just wanted to get some fresh air and soak up a little sun!

Next up: Quirky roadside photo op alert! There's a massive Pink Elephant wearing glasses at a gas station. His name is "Pinkie" and he was installed in the late 1970s at the gas station, now a Citgo. It's definitely the most adorable gas station on I-90!

If you're still in the mood for some more offbeat adventuring, head to the Circus World Museum in Baraboo, Wisconsin. This town was where the Ringling Bros. Circus was founded in 1884 by five brothers. In fact, they named the city the "winter quarters" for the circus, Ringlingville. Several buildings were built along the Baraboo River between 1897 and 1918, and today they make up America's "largest surviving group of original circus structures." Here you can see memorabilia and learn all about circus history, which is actually pretty interesting.

And if you want a good book to read on the road, Katherine Dunn's "Geek Love", will definitely get you in the mood to fully enjoy your time at the Circus World Museum.

From clowns to witches...over in Wisconsin Dells, skip the water parks (did you know that Wisconsin Dells has more waterslides per capita than anywhere else in the world?) and head to the Witches Gulch. It's like something out of Lord of the Rings! Admission to get in is just $5 and it's an absolutely breathtaking geological wonder. The Gulch is a slot canyon that surrounded by lush woodland. It's pet-friendly and definitely worth a visit if you're in the area.

And if you do actually want in on the waterpark action at the Water Park Capital of the World, we love the quirky offerings at Kalahari Resort!

If you're still in the mood for some outdoor fun, your next stop along the highway is Mill Bluff State Park near Camp Douglas, Wisconsin. This state park has beautiful, towering bluffs, swimming areas, a campground and plenty of places to hike or relax after a long day of driving.

Then, head down County Highway Q, just off I-90 to visit the FAST Fiberglass Mold Graveyard. This is a super quirky stop and a totally fun place to wander around and snap pictures. The grounds are full of molds that were used for all those iconic fiberglass roadside giants that dot the country (especially on iconic, classic routes like Route 66). It's free to walk around, just pull into the visitors area, and be courteous, respectful and don't climb on anything, because they're still a working Fiberglass shop. This is a great place to check out, and it's totally off-the-beaten path.

If you've got a sweet tooth, then do yourself a favor and visit The Pearl Ice Cream Parlor and Confectionary in La Crosse. Here you can sit back and imagine you're in the early 1900s, just enjoying a fountain soda, made from scratch in an old-fashioned soda shop. They also have handmade chocolates, and a candy selection that's to-die-for.

Once you hop the border to Minnesota, pull into the SPAM Museum in Austin. Even if you're not a fan of SPAM, this is a pretty cool museum that covers the history of this processed meat. Also, there's loads of SPAM merchandise in the gift shop (hello Christmas presents!) If you do enjoy SPAM, there's often a vendor out front selling SPAM burgers.

Once you get to Blue Earth, Minnesota, worship at the feet of the massive Jolly Green Statue! Towering at over 55 feet tall, the giant is a cultural icon and it makes for an awesome photo op. There's a small gift shop on site; it's not open all the time, but there's plenty of parking and you can get your picture at any time of day with the giant. It's very close to I-90, and it's very easy to hop on and off for the photo op.

Over in Garretson, South Dakota, you'll come to your second gulch! This one is Devil's Gulch Park. This natural chasm has secured its place in history as the spot where Jesse James jumped (with horse!) while escaping from authorities after he had robbed a bank. The whole area is quite beautiful and there's even a waterfall. There's a visitor center at the gulch, and you can learn about the science and history of the area here. There's also a walking tour that will take you about an hour, but it's totally worth it if you're taking your time here.

Next up, is 1880 Cowboy Town in Sioux Falls! Again, I-90 can get pretty monotonous, so take advantage of these offbeat attractions. Sadly, 1880 Cowboy Town has seen better days (okay, fine, a lot of the mannequins and exhibits are pretty dated) but to be honest, the rundown nature of the place actually adds to its appeal. Plus there are some nice exhibits on the history of Sioux Falls here.

Next is America's "corniest" attraction. It all started back in 1892 when the town of Mitchell, South Dakota was home to just 3,000 residents. Folks wanted a place to gather and celebrate their bountiful South Dakota corn harvests, and thus the Corn Palace and Corn Palace Festival were born.

The Corn Palace grew so quickly that in 1905, a new Corn Palace had to be built, and then another newer and even bigger palace was unveiled in 1921. This is the Corn Palace we all know and love today. If you’re headed through South Dakota, the Corn Palace is a must-see, and if you’re going through South Dakota in late August, you’ll be in for a real treat: the Corn Palace Festival…a giant 5-day party to celebrate all things corn.

At the State Historical Society in Pierre you can get a great sense for the culture of South Dakota by immersing yourself in the state's history. From Native Americans to the early European settlers, there's plenty to explore, and the museum's gorgeous displays do an excellent job of uncovering the history of South Dakota. Plus the building itself is gorgeous!

I-90 passes through a ton of American history as well. The Wounded Knee Massacre occurred on December 29, 1890, near Wounded Knee Creek, when the U.S. 7th Cavalry Regiment engaged in battle with the Lakota tribe in an effort to disarm them. 50 U.S. soldiers were killed, and at least 150 men, women, and children of the Lakota tribe were killed during the battle. Today you can pay your respects at the Wounded Knee Massacre Monument.

The Minuteman Missile National Historic Site offers a great tour and there's a very informative visitor center onsite. If you have time, take the guided tour through the control center. The tours are by appointment, so prepare to allow a bit of extra time... but it's worth it for this rare bit of Cold War history!

The Buffalo Gap National Grassland is a great place to either take a scenic cruise past one of America's "most extensive, productive ecosystems", or get out and take a quick stroll. The prairie seems to stretch on forever!

Your next stop is Wall Drug Store. Yes, it's a "tourist trap" but it's become something of an icon in this part of the country. The coffee is only 5 cents, and it's pretty good! There's also loads of kitschy gift shop stuff to buy, too.