Start from 31 curated places around Madison, IN, then choose the recommendations that fit your guests.
Restaurants & cafés
Key West Shrimp House
A Madison institution perched on the Ohio River waterfront, this place has been feeding locals and river travelers fried shrimp and catfish in a no-pretense setting for decades. The boiled shrimp is the move — simple, fresh, and absurdly cheap by any standard. Grab a waterfront table when weather allows and watch the river while you eat.
Hinkle's Hamburgers
Open since 1933, Hinkle's is one of those rare burger counters where nothing has changed and nobody wants it to — small, thin patties cooked on a well-seasoned flat-top with onions and served on steamed buns. The milkshakes are made the old way and the stools at the counter fill with regulars who've been coming since childhood. This is the platonic ideal of a small-town burger joint.
Trails & outdoors
Clifty Falls Main Gorge Trail
The signature trail in Clifty Falls State Park drops into the canyon carved by Clifty Creek and delivers the park's most dramatic scenery — sheer sandstone walls, multiple waterfall overlooks, and a creek-side walk that feels genuinely remote. The loop to Hoffman Falls and back is about four miles and involves real elevation change. This is not a stroller trail, but the payoff is exceptional.
Little Clifty Falls Loop
A shorter, slightly less strenuous loop within Clifty Falls State Park that still delivers genuine waterfall scenery without the full commitment of the main gorge trail. Little Clifty Creek drops over a series of limestone ledges in a setting that feels tucked away and private even on busy park days. Ideal for visitors who want the full experience in a more manageable package.
Things to do
Madison Regatta
One of the oldest unlimited hydroplane races in the country, the Madison Regatta transforms the Ohio River waterfront into a roaring festival every Fourth of July weekend — boats hitting 150 miles per hour on the river, live music, and a crowd that takes the whole thing very seriously. It's the biggest event in Madison's year and the energy is electric. Book accommodation months in advance if you're planning to attend.
Ohio River Steamboat Festival
Each fall, the Madison waterfront hosts one of the region's best steamboat festivals — working sternwheelers tie up at the public landing, calliopes play, and the whole riverboat era gets a vivid, loud, completely earnest tribute. It's genuinely festive in an old-fashioned way that Madison pulls off better than most river towns. The boat tours during the festival are not to be missed.
Landmarks & sights
Madison Historic District
One of the largest intact historic districts in the Midwest, spanning 133 blocks of Federal and Greek Revival architecture that has barely changed since the antebellum era. Walking these streets feels less like a museum and more like the town simply never got around to tearing anything down — which is exactly why it earned National Historic Landmark status. Start at the corner of Main and Second and just wander.
Lanier Mansion State Historic Site
Built in 1844 for banker and financier James F.D. Lanier, this Greek Revival showpiece sits steps from the Ohio River and is one of the finest examples of the style in Indiana. Lanier personally loaned the state of Indiana over a million dollars during the Civil War to keep troops in the field — and this house tells that story compellingly. The costumed guides are genuinely knowledgeable and worth every minute.