Interstate 90 (AKA I-90), is a coast-to-coast, transcontinental freeway, and it just so happens to be America's longest Interstate Highway. Unless you've only traveled around the southern portion of America, you've probably hopped on and off I-90 at some point, whether you boarded around Boston, Chicago or Seattle. I-90 is a whopping 3,020 miles long, after all! In the east, I-90 begins right by Boston's Logan Airport, passes through the Continental Divide by Butte, Montana and ends in Seattle, near Safeco and CenturyLink Field. Whether you're taking it all the way or just for a few miles, these are a few of the best I-90 road trip stops.
If you're starting in Boston, there are loads of places to check out from the New England Aquarium, to Faneuil Hall (where you can choose from dozens of different food vendors for a taste of Boston), to the Freedom Trail and Museum of Science. As for hotels in Boston, the Liberty Hotel is a former jail with tons of subtle nods to the building's past.
From Boston, stop at Old Sturbridge Village in Sturbridge, MA where you can literally step back in time to the 1830s. What separates this outdoor living history museum is that it happens to be the Northeast's largest living history museum. Here you can experience what life was like in the late-1700s to mid-1800s. There are over 40 original buildings, and the staff is always in costume, and focused on 100% authenticity. The best time to visit to avoid crowds is spring, and fall. In fact, autumn is the perfect time to visit to get gorgeous photos while the village is blanketed in stunning fall foliage. BONUS: If you happen to visit during Thanksgiving, they have an out-of-this-world buffet.
Six Flags New England is a pretty remarkable amusement park because it actually dates back to 1870, and has the distinction of being the oldest Six Flags park. The park is spread out across 235 acres and when you buy a pass to the park, you get to go to the waterpark as well. When you go be sure to ride the Thunderbolt, a wooden roller coaster that's been in operation since 1941. It's not exactly a quick stop off the highway, but it's an incredibly fun way to spend a day!
If you're a fan of Michael Jackson, then you'll definitely want a photo at his childhood home in Gary, Indiana, which is right off the interstate. The best time to visit is in August, when there's usually a Michael Jackson-themed event going on.
If you love Saturday Night Live, or just really dig improv comedy, then you need to visit the mecca of improv: The Second City in Chicago. This is where the best SNL cast members got their start.
TIP: If you purchase tickets through the Second City website you can usually get a great deal on a restaurant nearby at the same time. Dinner and a show in Chicago: The perfect night out on the town!
And if you want a hotel in Chicago, the options are almost endless. Hotel Lincoln, Hotel Monaco, Hotel Burnham... take your pick! They're all great.
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!
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!
Depending on the time of year you decide to drive I-90, it's important to note that weather can affect your journey. Snow and high winds will plague you from Minnesota to Montana, especially in the winter. Snow plows do a pretty good job, but if there's a storm, you could get stuck, so be prepared before setting out for this trip. Also, keep in mind that between Rapid City and the Black Hills, you'll be at an exceptionally high elevation, which means it's a bit more colder in this area. Pack accordingly, depending on the time of year. In fact, during deep winter, you can expect sub-zero temperatures across South Dakota, Wyoming and Montana. Remember your anti-freeze, snow tires, and don't let yourself run low on gas.