An Underrated Indiana Gem: Discover the Riverfront Charm and Delicious Cuisine of One of the Midwest’s Best Small Towns

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An Underrated Indiana Gem: Discover the Riverfront Charm and Delicious Cuisine of One of the Midwest's Best Small Towns

If we were to recommend a Midwest city called Madison next to the water and full of gorgeous scenery and eclectic eateries, you might assume we’re talking about Madison, Wisconsin (aka the home of Wisconsin’s mysterious “lost city” in an enchanting forest). However, if you go about 400 miles southeast, you’ll run into a city with the same name in a different state: Madison, Indiana.



While this Madison isn’t as large as the one further north, it’s just as much of a Midwest gem. Being by the Ohio River, the city gets some incredible riverside views, and because the city doesn’t get as crowded as other metropolitan areas, you can enjoy everything it has to offer without paying high prices or waiting in line for high-quality restaurants and experiences. While Indianapolis gets around 30 million visitors annually, Madison gets a fraction of that. In fact, this Madison is so awesome that it was ranked as the Best Small Town in the Midwest by USA Today.

So, if you’re looking for a fun, relaxing Midwest travel destination that offers all the gourmet food, history, and amenities of a major capital without the crowded streets, Madison, Indiana, should be on your list. Whether you choose to make the pilgrimage via a road trip or airplane, here’s everything you need to know about this hidden gem.



Getting to know Madison, Indiana

Many small towns sprang up along the Ohio River in the 1800s. Much like the Kentucky town of Maysville hidden on the Ohio River that’s full of historic charm, Madison rose to prominence as a transportation hub for the area. Established in 1809, Madison quickly became a prominent city in the region, even receiving the nickname “Porkopolis” because of its extensive agricultural output.

But while Madison enjoyed fame and fortune during the mid-1800s, other cities like Indianapolis started stealing the spotlight. However, Madison’s decline in population allowed the city to preserve more of its history than other towns along the river. Today, Madison is considered the largest contiguous National Historic Landmark District in the country, with over 1,800 buildings. You can wander through impressive sites such as the River Docks, the Schofield House, the Broadway Fountain, and the Lanier Mansion State Historic Site, aka the “Crown Jewel” of Madison’s Historic District.

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After exploring the Historic District, the rest of Madison will almost feel like a completely different city. Instead of brick buildings and densely-packed streets, North Madison is much more spread out and modern. Even the food differs from one side to the other, with unique gourmet restaurants by the river. Some of the best pubs, taverns, and grills are on Main Street in the Historic District, including Rivertown Grill, Red on Main, Shipley’s Tavern, and the River Oak Chophouse.

Planning your trip to Madison

Dave Pennells

By Dave Pennells

Dave Pennells, MS, has contributed his expertise as a career consultant and training specialist across various fields for over 15 years. At City University of Seattle, he offers personal career counseling and conducts workshops focused on practical job search techniques, resume creation, and interview skills. With a Master of Science in Counseling, Pennells specializes in career consulting, conducting career assessments, guiding career transitions, and providing outplacement services. Her professional experience spans multiple sectors, including banking, retail, airlines, non-profit organizations, and the aerospace industry. Additionally, since 2001, he has been actively involved with the Career Development Association of Australia.