Madison, Indiana is one of the most culturally-rich destination towns you’ve probably never heard of. But here’s why you need to visit – check out our list of can’t miss things to do in Madison Indiana below!

A quick 5-hour drive south from Chicago, Madison, Indiana will make you feel alllll the southern charm feels without the plane ride or swampy humidity. The historic river town is situated right on the Ohio River (which essentially acts as the state border between Indiana and Kentucky) and is full of landmarks and architecture, boutiques and treasure troves of antiques, and nationally-known, locally-sourced eateries. Below is a bookmarkable bible of things to do in Madison Indiana.

Lanier Mansion - things to do in Madison Indiana

Madison Indiana Hotels

In addition to inns, quaint B&Bs, the eagerly anticipated Fairfield Inn on the Madison Riverfront, you can also stay in a little piece of history at the Fashion House on Central. This gorgeous Greek Revival landmark has been renovated by local entrepreneur, educator and philanthropist Mary Beth Boone. She and her husband have been bolstering business in the Madison community for years and the Fashion House on Central is no exception – the 4-bed, 3-bath accommodation comfortably sleeps 12 and offers tons of unique bookable amenities, such as a visit from an in-home chef (she’s from Peru), pampering and personal shopping courtesy of the attached boutique, salon and studio, plus a first-hand look at their new recording studio. The Fashion House on Central is also a premier destination for those headed to the Kentucky Derby – but make like a Triple Crown winner and act fast because it books up!

Madison Indiana Restaurants

From farm-to-table dining to greasy spoon diners that will have you licking your plate, the list of eateries does not disappoint. A few can’t-miss spots:

Things to Do in Madison Indiana – Slide into Hinkle’s Sandwich Shop

Hinkle’s made sliders a thing before they were a thing. If you are a burger person, you absolutely cannot pass this spot up. Started by Mr. Winfred Hinkle in the 1930s (while trolley cars were still going up and down Main Street), Hinkle’s Sandwich Shop has been creating smashed patties of goodness for over 80 years.

Order like a local and get a few singles, doubles or triples “with pickle and onion” and home fries with cheese – either as lunch or a late-night bite (they’re open 24 hours on Friday and Saturday!). Plan accordingly though, they’re closed on Sundays.

The Attic Coffee Mill Cafe

The Attic & Coffee Mill Cafe

Located just west of the main downtown area, the Attic is a great place to stop for some fuel before you explore. The 4th generation shop has been serving house-roasted and brewed artisan coffee since 1971. Not only that, but they also offer their own coffee for purchase, gifts, and an extensive breakfast and lunch menu. And they may or may not have a humongous selection of baked-in-house.

Crafted Coffee Co.

Another delightful spot to caffeinate, plan to spend a little time luxuriating with your latte here because the interior is adorable and the views of Main Street are perfect for people watching. Their food is great for refueling – the Binzer Breakfast Sandwich is a favorite (and a nod to the framing company next door).

Little Bakery Haus & Cocoa Safari

Madison has TONS of places to satiate anyone with a sweet tooth. Little Bakery Haus should be your go-to for donuts… except you’ll have to visit early because they sell out quick. In addition to donuts, Cocoa Safari has an impressive selection of chocolates and is positioned perfectly for a mid-Main Street pit stop.

Gallery 115

If you ever thought to yourself, gee, I wish a delicious café was inside a beautiful art gallery, then you’ve come to the right place. Definitely killing two birds here – Gallery 115 is a unique situation that only can be found in a place like Madison.

Red Pepperoni

Walk a few blocks and you’d be hard pressed to find an establishment NOT part of the ‘red’ group – the Red Peppermint, Red Pepper Café, Red Roaster – are all part. Red Pepperoni is the pizza place of the group – and you definitely need to pay them a visit; made-from-scratch crusts all day. Grab a brew and save a spot on their porch when it’s nice out!

Off Broadway Taproom

Great spot to grab a burger and especially a show – the Off Broadway Taproom has live music performances frequently – especially during festival weekends.

Mad Paddle Brewery

Fun fact: Madison is actually a pretty famous spot for brewing beer. Mad Paddle Brewery is a nod to the history of the town; the building is actually the oldest standing brewery building in the state of Indiana. Pair the brews with bites from food partner Uncommon Pizza and be sure to stop by when its warm out, when there are live performers on the sunny patio!

Things to Do in Madison Indiana

This small but mighty town has a seriously impressive list of things to see and do. Choose from monthly festivals, local shops, historical landmarks, wineries – and even a nationally-renowned state park!

Did Someone Say Festivals?

If you love a good festival, you’ve come to the right place. The beauty of Madison is that they have so many – and they’re not just during the summer months. One major favorite is Chautauqua Festival of Art, during the end of September/beginning of October. Booths upon booths of local artisans offer everything including jewelry, clothing, leather goods and wood products. Definitely get your hands on some cutting boards if you can! Check out the full list of major fests below:

  • RiverRoots – May
  • Madison Regatta – July
  • Ribberfest – August
  • Chautauqua Festival of Art – September

Side note: the Madison Regatta involves hydroplane racing which is pretty much the closest you’ll ever get to hover cars (unless you hang with the SpaceX team or something) and it’s super cool. Definitely go if you can!

Shopping the Boutiques

Blush on Main is a unique boutique from Mary Beth Boone (check out her recent interview here!) that also houses a hair salon, a florist, a photography studio and more and is definitely a must visit for picking up seasonal pieces no one else will have. They also offer accessories (they were recently featured for their famous selection of Kentucky Derby hat “fascinators”), home goods and tons of one-of-a-kind gift items. Another awesome boutique? Betty Jeffries. Resident artist Maria Napoli creates gorgeous works on canvas AND clothes. You’ll also find other great accessories and fashion there for all seasons. Other hot spots? Crawdaddy Music, Bourbon & Bird Dogs menswear, Fountain Alley, Hertz Shoes & Little Golden Fox. Madison also offers a treasure trove of spots to find great antiques.

Outdoor Recreation in Madison, Indiana

Though the New Buffalo region is technically the “Napa of the Midwest” – Madison is another serious contender. With 7 wineries within a 30 – 60ish minute drive (and many within the downtown area, like Thomas Family Winery) of the city, Madison is perfect for a girls getaway or any other reason you can think of to celebrate. Check out the full list here.

Madison Riverfront

Shopping, antiquing and wine tasting not your idea of things to do in Madison Indiana? Walk down to the Madison Riverfront, where you can mosey along the meandering river, or walk across the Milton/Madison bridge for a scenic lookout point. Or, head down to the beginning of the Heritage Trail and head up ‘The Cut’ – the Madison Railroad Trail – a once-operating line that actually is the steepest inclined railroad track in the US. You’ll find a TON of amazing fossils in the gorges. Another place to spot fossils?

The Cut Railroad Track in Madison Indiana

Clifty Falls State Park

Clifty Falls State Park offers scenic hikes and glimpses of the past through collections of from an ancient marine life (including corals, squids and brachiopods for all you paleo-nerds out there). The park is also home to a number of stunning waterfalls that range in activity throughout the seasons. It’s also a perfect place for camping!

Related: other surprising places to hike in the Midwest? New Buffalo Michigan! Check out the Indiana Dunes and the Indiana National Park!

Madison Historic Architecture District

More of an architecture buff? Fun fact: Madison, Indiana was ALMOST the state’s capital (because of its ideal position on the Ohio River and being a main entry point into the Indiana Territory, back in the 19th century). It’s also home to a record-setting 133 blocks of historic real estate, known as the Madison Historic Landmark District. Walking home tours are offered frequently, along with a ghost tours!

The Cut hiking trail - things to do in Madison Indiana

Whether a road trip stop or a long weekend getaway, Madison Indiana is definitely a destination to put on your list!