Buckle up, because this road trip is about to take you from the buzzing streets of New York City to the skyscraper-studded skyline of Chicago—with a whole lot of adventure in between.
We’re talking epic hikes, quirky small towns, crazy-good food, and some of the coolest hidden gems you never knew existed.
One minute, you’ll be standing in front of a legendary American landmark, and the next, you’ll be trekking through an epic canyon that doesn’t even look real.
Oh, and did we mention waterfalls, a glass-floored bridge, and a sandwich that’s bigger than your face?
So grab some snacks, queue up your best road trip playlist, and get ready for an adventure you’ll be talking about forever.
1. New York City, NY
New York City—loud, fast, and absolutely iconic—is where this epic road trip kicks off.
Grab a bagel, snap a pic of the skyline, and hit the road because the adventure starts now!
2. Philadelphia, PA
Welcome to Philadelphia, the city that gave America the Declaration of Independence and the best cheesesteaks you’ll ever eat.
Just a 1.5 to 2-hour drive from NYC, this place is packed with history—like the Liberty Bell which is one of the most famous symbols of freedom.
You can run up the Rocky Steps at the Philadelphia Museum of Art (bonus points if you blast the theme song) or wander through Reading Terminal Market for soft pretzels and Amish donuts.
Oh, and don’t leave without trying a Philly cheesesteak.
Pat’s and Geno’s have a famous rivalry, but locals might tell you to skip both and go to John’s Roast Pork instead.
3. Pine Creek Gorge, PA
Leaving the city behind, it’s time for some nature at Pine Creek Gorge, also known as the “Grand Canyon of Pennsylvania.”
The gorge is nearly 50 miles long, surrounded by rolling forests, towering cliffs, and a winding river that looks straight out of a postcard.
Hike the Turkey Path Trail for waterfalls and jaw-dropping views, or rent a kayak and paddle through the canyon.
If you’re here in the fall, get ready—because the autumn colors are so unreal, they make every Instagram filter look pointless.
4. Allegheny National Forest, PA
Next up, Allegheny National Forest—a massive, tree-covered playground where road trip fatigue doesn’t stand a chance.
This place is all about outdoor adventures, whether you’re hiking through old-growth forests or zooming down ATV trails.
You can also stroll along the Kinzua Sky Walk, a pedestrian walkway built on the remaining towers of the historic Kinzua Viaduct, featuring an overlook with a partial glass floor.
At the time of writing, the skywalk is getting a multi-year makeover and is currently closed.
Good news though, during peak fall foliage construction takes a break temporarily between August and October so you can still enjoy the views!
Be sure to check with the park for the latest updates before planning your visit.
Don’t miss the small town of Kane, where you can enjoy wines perfected over time at Bear Creek Wines—if you’re lucky, you might even spot a black bear.
The adventure doesn’t stop there—the forest is also home to the Allegheny Reservoir, perfect for kayaking, fishing, or just kicking back by the water with a snack.
5. Pittsburgh, PA
Rolling into Pittsburgh, get ready for a city that’s part steel-town grit, part artsy cool, and 100% underrated.
This place has 446 bridges (more than Venice!), a skyline that looks incredible from the top of Mount Washington, and a serious love for sandwiches stuffed with fries (shoutout to Primanti Bros.).
You can explore science and pop culture at the Carnegie Museums, experience the super-trippy Andy Warhol Museum, or catch a Steelers game if you want to feel true Pittsburgh energy.
Before you leave, swing by Randyland, a wild, colorful art installation that proves this city is way more than just football and factories.
6. Cuyahoga Valley National Park, OH
Crossing into Ohio, it’s time to stretch your legs at Cuyahoga Valley National Park, a surprisingly wild escape just outside Cleveland.
This park has it all—lush forests, winding trails, and Brandywine Falls, a 60-foot waterfall that looks like something out of a fairy tale (but, you know, without the dragons).
You can bike the Towpath Trail, following the old Ohio & Erie Canal route.
However, at the time of writing, the trail is scheduled to be temporarily closed from March 2025 to May 2025 for renovations, so it’s better to check online before you go.
Meanwhile, you can still enjoy a scenic ride on the Cuyahoga Valley Scenic Railroad.
Keep an eye out for beavers, blue herons, and maybe even a bald eagle.
7. Columbus, OH
Next stop: Columbus, the buzzing heart of Ohio that’s way cooler than people give it credit for.
Start in the Short North Arts District, where murals cover every wall, boutique shops tempt your wallet, and the food scene is straight-up fantastic (hot chicken at Hot Chicken Takeover is a must).
If you’re into science and history, the COSI Science Center has hands-on exhibits and even a full-size T. rex, while the German Village neighborhood is all brick streets and bookshops straight out of a storybook.
And if you need a caffeine boost, Columbus takes its coffee seriously—hit up Fox in the Snow for a latte and some of the most beloved pastries in the city.
8. Indianapolis, IN
Rolling into Indianapolis, get ready for a city that’s all about speed, sports, and seriously good eats.
The Indianapolis Motor Speedway is the crown jewel here—whether you’re a racing fan or not, standing on the track where the Indy 500 happens is pretty epic.
For a slower pace, bike the Cultural Trail, check out the larger-than-life outdoor art at Newfields, or wander through Mass Ave, where you’ll find indie shops and craft breweries.
And if you’re hungry, grab a legendary breaded pork tenderloin sandwich—Indiana’s deep-fried answer to “how big can a sandwich actually be?”
9. Turkey Run State Park, IN
After the city buzz of Indy, Turkey Run State Park is the perfect place to get back to nature—and maybe get a little muddy.
This park has deep sandstone canyons, wooden suspension bridges, and trails that take you through narrow rock crevices (yes, you might have to squeeze through a few).
Hike Trail 3 if you’re up for an adventure—it’s got ladders, waterfalls, and a whole lot of “wow, this is actually in Indiana?” moments.
Whether you’re paddling down Sugar Creek, spotting wild turkeys (yes, the park name makes sense), or just soaking up the scenery, this stop is pure outdoor magic.
10. Starved Rock State Park, IL
Crossing into Illinois, it’s time to explore Starved Rock State Park, a place that proves the Midwest has way more than just cornfields.
This park is packed with waterfalls, deep canyons, and hiking trails that lead to some seriously jaw-dropping overlooks of the Illinois River.
If it’s spring, the waterfalls are flowing; if it’s fall, the trees are showing off in every shade of red and orange; and if it’s winter, the frozen waterfalls turn the whole place into a scene from Frozen.
Climb up to Starved Rock Overlook for the best views, and if you’re lucky, you might even spot bald eagles soaring over the river.
11. Chicago, IL
And just like that, you’ve made it to Chicago—a city that does everything big, from its skyline to its deep-dish pizza.
Start with the classics: snap a selfie at The Bean, stand on the glass ledge at the Willis Tower Skydeck, and walk the Chicago Riverwalk, where the city’s best views come with a side of people-watching.
For food, you have to try deep-dish at Lou Malnati’s or a Chicago-style hot dog (no ketchup allowed!) at Portillo’s.
End the trip with a sunset stroll along Lake Michigan, because nothing beats the sight of the city lights reflecting on the water after an epic road trip like this one.
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