Windows down and the radio up — a visual that most likely evokes sweet memories of summertime road trips, the car loaded down with family, friends, and a truckload of snacks. With springtime on the horizon and the promise of warmer weather, it’s the perfect time to set out on the highway. Midwest locals, in particular, enjoy close living quarters to one of the best road trip routes in America. This 460 mile route from Pittsburgh to Chicago directs travelers on a winding voyage through some of the best highlights in the Midwest. Traversing four states in seven hours, road-trippers will pass through the urban maze of western Pennsylvania, the rural backcountry of Ohio, and the northern region of Indiana, before entering into Chicago’s urban metropolis.
Given its short distance, this miniature cross-country road trip is the perfect weekend getaway or extended summer or fall break excursion. June through September is often the best time to embark on this journey, with the warmer seasons providing optimal driving conditions and a host of summer festivals along the way. Of course, fall is the seasonal favorite in this part of the country, when the leaves display a vibrant montage of orange, red, and brown foliage, and hot apple cider stands entice you to pull over — and likely more than once. With your favorite Spotify playlist on shuffle and an iced latte in hand, a full tank of gas and a camera are likely all you’ll need on this exhilarating U.S. road trip route.
Pittsburgh to Indiana
Pittsburgh is commonly distinguished by its moniker, “The Steel City,” and is known as the home state of Carnegie Mellon University, but did you know this city is also famous for its pickles? Fans of this tangy specialty food will be delighted by Pittsburgh’s annual summer Picklesburgh, which was voted as the Best Specialty Food Festival in America by USA Today. You’ll find pickled everything at this event, from pickle juice drinking contests to foods and cocktails all based around the timeless classic.
Heading two hours northwest toward Cleveland, Ohio, this city is full of exciting hot spots that will have you shouting, “Let’s stop there!” Among such sights are the Rock & Roll Hall of Fame, the roller coaster capital, Cedar Point, and West Side Market, Cleveland’s oldest open-air market. This eclectic warehouse has captured the attention of several iconic news outlets, including the Travel Channel and Food Network, and showcases an array of local artisan products. On your way out, don’t forget to snap a picture of the real-life “A Christmas Story” house, featured in the timeless movie classic.
Just 20 miles outside Cleveland, Cuyahoga Valley National Park is a wilderness gem in this Midwest state. The national park is draped in lush greenery and situated along the Cuyahoga River with a captivating backdrop of rolling farmland, dense forests, and babbling brooks. The Cuyahoga Valley Scenic Railroad and the stunning Brandywine Falls are two sights in particular that make this state treasure one of the best highlights along the route.
Indiana to Chicago
Rounding out the back half of this trip, you’ll enter the Crossroads of America, Indiana. Home to acres of open farmland, this state loves to put its bread and butter on display in a series of fun festivals spread throughout its annual calendars. There’s always something to discover in this state, no matter what time of year you find yourself passing through.
Fall visitors will be treated to the annual Valparaiso Popcorn Festival, located in downtown Valparaiso in Porter County, 50 miles outside Chicago. This local tradition hosts a popcorn parade, popcorn races, and every flavor of sweet and salty popcorn imaginable. Consider extending your route to include Northern Indiana’s Heritage Trail, one of America’s most scenic drives. This stunning road winds through some of the state’s most picturesque downtown areas, exposing the rich heritage of small-town American life in all of its old-fashioned charm.
Marking the landing point on this road trip is the deep-dish pizza capital of the world — Chicago, Illinois. Obviously, tracking down the best slice in town is the first thing one must do when crossing the state lines. Surprisingly, locals love their thin-crust pizza just as much as they do deep-dish style. Pizza City USA is the only food tour in America run by a James Beard winner, so you know it must be good! Famous for delivering four styles of pizza in just three hours, it’s the perfect place to cap a road well traveled. Bon appétit!
