Indianapolis Area Real Estate Blog

On the Road Again: An Indiana Road Trip Guide


Everybody needs a breather now and then, but full blown vacations can be hard to come by. That doesn’t mean, you need to forego the relaxing qualities of getting away. Indianapolis just happens to be central to a huge number of fantastic little retreats which would appeal to a broad range of interests, all situated about 5 hours or less from home, or in other words, close enough to make a 3- day weekend a bona-fide treat. Here’s a virtual tour of a few itineraries!


The Outskirts of Chicago may be a no-brainer destination from Indy, but did you know there are lots of equally charming and less crowded suburbs of Chi-town which are more than worth visiting? Take, for example, the absorbing little town of Glen Ellyn just 23 miles west of Chicago, whose adorable boutiques and Tudor-style downtown streets make for a great girls get-away. It could also be a good option to stay outside of the city and then take a day-trip in, depending on how much time you have! Try Waterleaf, a French and American white tablecloth affair, and then catch a rest at The Inn at Water’s Edge

Bonus: If you detour about 30 minutes East of 65 in Gary, you’ll come to Michigan City, where the Lighthouse Place Premium Outlets live. This is an extraordinary outlet with an enormous collection of stores, including BCBG, Banana Republic, Anne Taylor, Michael Kors and Kenneth Cole.

The River Road from Ottowa to Havana - Although it sounds exotic and far, it’s actually just a lush, scenic run between two cities in Illinois, perfect for nature lovers. Along this national scenic byway you can take in the waterfalls and canyons of Starved Rock State Park and then visit the Chataqua. 

National Wildlife Refuge is home of over 200,000 birds of all varieties. Then, visit the Mark Twain Hotel, and resolve the stretch at August Hill Winery.

Galena, Illinois - Nestled along the Mississippi river, this little gem has over 100 shops and restaurants, as well as lovely scenic attractions. It was recently voted one of America’s top 10 best small towns, you’d be in for a sweet treat with this pick. 


Of course, Ohio has Kings Island and Cedar Point and the world-famous Tony Packo’s hot dog, but our Eastern neighbor has more to love than that!

The Hocking HillsA sprawling state park area in Ohio full of every piece of nature appreciation you could possibly want. Everything from gorges, forrest, cliffs, bird watching, star programs, caves, waterfalls, trails, cabins and more. If a nature getaway is your thing and you’ve done everything here at home, this would be a big win. Hocking Hills also has a quaint collection of little artisanal shops, reminiscent of Nashville, Indiana

ClevelandTake a morning at West Side Market, a sprawling public market with origins all the way back to the 1840’s. Browse the 100+ vendors who pedal everything from cheeses and herbs, to flowers, produce and meats. Then wander the Cleveland Botanical Gardens, the incredible Wade Chapel, catch an Indians game or spend one of your get-away days in the wild, peaceful Cuyahoga Valley National Park.

The VineyardsWhile it might not be napa, there is a wine trail as nearby as Ohio, running along the Southern border of Lake Erie. With covered bridges, scenic drives, and Bed and Breakfasts galore, you can’t miss if you’re looking for some ultimate relaxation. Check out for more info.


If you’ve the all of the usual spots; Brown County and French Lick, here are a couple of others worth trying:

Madison - Sitting perched on the edge of the Ohio, Madison is as lovely as she is charming. With a downtown full of shops, restaurants, galleries and B&B’s, it’s sure to be a home run for a weekend getaway. In the Summer, Madison hosts the Madison Regatta, an event with live music, street vendors fireworks and of course, amazing regatta racing.

Nappannee - Sometimes a person can hunger for the simpler things and that’s what you’ll find in the old Amish countryside of Nappannee. Visit the rustic and beautiful Amish Acres where you can sample the lifestyle and the delicious country fare.


LouisvilleYou might be surprised to find that Louisville has quite the range of amenities to take advantage of, including it’s world famous glass blowing, the Urban Bourbon Trail, or the Louisville Slugger Museum and Factory. And then, of course there are specific events like the Kentucky Derby or the St James Court Art Show, held in the fall. 

Where are some of your favorite places to road trip? Comment below. We want to know!

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