Distance: 70 miles | About 1 hour, 10 minutes
What to Do: Named one of the most beautiful towns in Ohio by Culture Trip, Yellow Springs, Ohio offers a mix of unique shops, restaurants, theaters and museums. But it's the incredible wilderness that makes this spot so desirable! With multiple orchards in the area and over 2,000 acres of woods complete with cycling and hiking trails, you won't run out of things to do any time soon!
We recommend visiting Glen Helen Nature Preserve, which features 25 miles of footpaths that allow you to explore streams, woods and fields, plus the town's namesake: Yellow Spring! If you have extra time, stop by Clifton Gorge, for incredible rock and waterfall views, and John Bryan State Park, where you can get a peek of the Little Miami River and a stunning limestone gorge.
Things to See Along the Way: On your drive, you'll pass by some famous Ohio spots that are definitely worth a visit, including the historic Loveland Castle & Museum, the massive National Museum of the US Air Force, and an eclectic 8-acre corn maze!
Where to Stay: Mills Park Hotel
Distance: 116 miles | About 2 hours, 10 minutes
What to Do: Nashville, Indiana is what small town USA dreams are made of. Nestled among bountiful woodlands, this area offers plenty of outdoor adventures like zip lining, mountain biking and horseback riding. The small town itself is ripe for exploring with several art galleries, historic sites and antique stores sprinkled throughout the area.
We recommend stopping by the T.C. Steele State Historic Site, a home and studio that teaches about the Hoosier Group impressionist who was largely responsible for turning Brown County into an artists' colony. And, if you have time, visit the Bean Blossom Bridge, a bright red, covered bridge that once served as a major passage into the area. Today, it's the perfect end destination on a hike or a great location to knab a rustic photo for your Instagram feed.
Things to See Along the Way: Your drive from Cincinnati to Nashville, Indiana is one of the most beautiful road trips around. You'll pass by several parks, ranches and farms — all perfect places for picnics and wilderness excursions!
Where to Stay: The Brown Country Inn
Photo courtesy of Loretta Coblentz via The Barn Inn Bed & Breakfast
What to Do: If you haven't visited Ohio's Amish Country yet, you're in for a treat. Holmes County, Ohio is home to the world's highest Amish concentration and the idyllic area features gently rolling hills and charming farms. While you can't go wrong with visiting any of the 10 tiny country towns around the area, Millersburg is a fantastic starting point. Get a taste of an authentic Amish experience at Yoder's Amish Home, a 116-acre farm open for tours almost every day. Take a tour of Heini's Cheese Chalet, home of one of the most famous products that comes out of Ohio's Amish Country. There are so many things to do in the area, you can make an entire weekend out of it, but if you don't do anything else in the Amish Country, you absolutely have to stop and grab something to eat. The area boasts some of the best cozy restaurants around, including Tarragon at the Inn at Honey Run, The Chalet in the Valley and Mrs. Yoder's Kitchen — all offering mouthwatering, homecooked meals that are crafted with fresh and seasonal ingredients. Things to See Along the Way: The trip to Millersburg is pretty much a straight shot, passing right through Columbus! Stop for a spontaneous lunch at one of our favorite restaurants that don't require reservations or grab a coffee to fuel the rest of your journey at one of the best coffee shops around. Where to Stay: The Barn Inn Bed & Breakfast
Distance: 239 miles | About 4 hours, 20 minutes
What to Do: Located on South Bass Island just off of the coast of northern Ohio, Put-In-Bay is a beloved summer getaway from people all over the Midwest! This gorgeous town draws nearly two million visitors each year all due to the charming shops, fantastic fishing opportunities and excellent restaurants.
Due to Put-In-Bay's incredible location on the coast, kayaking, swimming and boating are all great choices of activities in the area! And, amusement park enthusiasts should definitely pay a visit to Cedar Point before you leave. This incredible park is consistently ranked among the best in America and offers some of the best roller coasters, rides and petting zoos around.
Things to See Along the Way: If you feel like stopping during your trip, there are plenty of museums and attractions along the way! The Bicycle Museum of America, Neil Armstrong Air and Space Museum and Gene Autry Mural & Park are only minutes away from your route and offer some truly spectacular sights.
Where to Stay: Put-in-Bay Resort
Distance: 294 miles | About 4 hours, 40 minutes
What to Do: There are plenty of things to do and see in the Windy City, from exploring Millennium Park and getting a photo with the illustrious Bean to getting a thrill at 1,353 feet at the Willis Tower Skydeck. One of our favorite things to do in the area is visiting the Art Institute of Chicago, which is filled with masterpieces from every era. Travel Tip: Enter the museum on the Monroe Street side instead of on Michigan Avenue, you'll encounter fewer lines and will be able to get out of the Chicago heat faster!
While you probably won't be able to see the whole city in one day or even a weekend, there are a few essential spots that you should visit to get the full Chicago experience. Grab a slice of the city's famous pizza at Pequod's; see a show at Second City, where Bill Murray, Tina Fey, Gilda Radnor and many other SNL alumni got their start; and take a leisurely stroll along the Lakefront Trail, where you'll get stunning views of both the Chicago skyline and Lake Michigan!
Things to See Along the Way: Stop halfway in between Cincinnati and Chicago in Indianapolis. If you only have time to see one thing, check out the largest children's museum in the world — the Children's Museum of Indianapolis. Inside the massive museum, you'll find a planetarium, a carousel, science labs and so much more!
Where to Stay: Freehand Chicago