Madison, Indiana is one of the most culturally-rich destination towns you’ve probably never heard of. But here’s why you need to.
A quick 5-hour drive south from Chicago, Madison 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.
Where to Stay in Madison
Full disclosure, I have developed a close affinity for the adorable town of Madison because my husband grew up there. We met at Indiana University (go Hoosiers!) and I have been bringing an outsider’s perspective and appreciation to the city for over 7 years. We stay at his parents’ house, but there are TON of great places to stay that are close to the downtown area and other points of interest. You can see the list on TripAdvisor here.
What to Eat
If you’ve read any of my other city guides (especially these food-heavy guides to Barcelona and Florence), you know how much importance I put on quality places to stuff one’s face. Madison is no exception. 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 of my personal favorite can’t-miss spots:
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 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
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 goods (which I fall prey to every time I’m in there. Oops).
Crystal & Jules
Mentioned in the Indiana Office of Tourism Development’s 2016 Bicentennial Edition of the Official Indiana Travel Guide, Crystal & Jules is an upscale dining destination not to be missed. Plenty of Italian flavor-focused meat and seafood options mean there is something for everyone – including their fresh house-made pasta dishes. They are also famous for their dessert selection. If you know me, you know there is ALWAYS room for dessert. I highly recommend the crème brûlée!
The Sweet Spot(s): Little Bakery Haus & Cocoa Safari
As I mentioned, I LIVE by the mantra “there is always room for dessert.” (This is also why I run 5 miles at least twice a week… most of the time). Madison has TONS of places to satiate anyone with a sweet tooth. I am constantly begging Riley to go to the Little Bakery Haus for donuts… except they are usually always gone by the time we get up in the morning. Definitely stop by if you can! In addition to donuts, Cocoa Safari has an impressive selection of chocolates and is positioned perfectly for a mid-Main Street pit stop.
Things to Do
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’re like me, you love a good festival. The beauty of Madison is that they have so many – and they’re not just during the summer months. My personal favorite is the 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 some of my favorite 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!
Blush on Main
Without fail (and much to Riley’s chagrin), I visit Blush on Main every single time I am in town. A unique boutique that also houses a hair salon (and as owner Mary Beth Boone told me, a florist, which is coming soon!) this 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. Madison also offers a treasure trove of spots to find great antiques.
Wineries, Nature & Landmarks, Oh My!
Though the New Buffalo region is technically the “Napa of the Midwest” – I’d say Madison is another serious contender. With 7 wineries within a 30 – 60ish minute drive (and many within the downtown area) 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.
Shopping, antiquing and wine tasting not your thing? Clifty Falls State Park offers scenic hikes and glimpses of the past through collections of fossils 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!
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! You can learn more here.
Like I said, Madison is such a culturally-rich hidden gem I’m surprised it took me marrying into it to discover its charm. Whether a road trip stop or a long weekend getaway, it’s definitely a destination to put on your list!
