Eat, See, Do: Madison, Indiana Guide

Madison Indiana guide

I had low expectations rolling into Madison. All I knew was it was a decent sized town overlooking the Ohio River and that it was under two hours from Indy. Surprisingly, I hadn’t done much of normal research so I was flying by the seat of my pants. But as I descended into the valley heading towards Madison and the river, I knew I had made a good choice.

(NB: if you have the chance, come in via Old Michigan Road. You’ll get a real taste of Indiana farm country and how it used to be when visiting Madison!)

Madison (a town of about 12,000) is, in a word: delightful. It’s been described as both “the prettiest small town in the Midwest” and “Best Preserved Town in the Midwest”. Madison is an absolute charmer and I only wished I had planned better. It’s definitely not a town to just spend one afternoon in!

But nonetheless I’m here to share some gorgeous pictures and my very own humble Madison, Indiana guide. If you’re not satisfied after this list (and you shouldn’t be! there’s so much more!), go ahead and check out Visit Madison to get some official information on what else you can expect from Madison, Indiana!

Wander downtown!

Madison’s architecture is wonderfully preserved. And when I say that, I mean the downtown looks like something straight out of a history book. Brightly colored buildings contrast brilliantly with the blue sky, making the streets something truly special. Best of all, there were hardly any empty storefronts – the bane of any small town’s existence.

But Madison’s main street isn’t the only star: the town boasts 133 blocks on the National Register of Historic Places, 3 National Historic Landmarks, and the largest contiguous National Historic Landmark District in the whole USA. When I say there’s something breathtaking around every corner, I literally mean just that.

Shops to visit: there are tons of antique shops in Madison but my favorite was the Main Street Antique Mall, which was more an eclectic hodgepodge than the other more curated shops. For a spot of luxury, try All Good Things Soaps & Such. For a little bit of reading and relaxation, hit up Villiage Lights Bookstore – grab a book and pet a cat!

What to eat: Hinkles Sandwich Shop for perfect diner vibes, The Red Pepper Deli Cafe for a super-quick bite, and Cocoa Safari Chocolates for a sweet tooth! I also really want to go back and try Bistro One, whose tagline is “Think Globally; Eat Locally”.

Special Mention: Galena Garlic Company

Madison Indiana Guide-9
I don’t know what it is about specialty olive oil, but I just can’t get enough of it! The Galena Garlic Company has a vast variety of flavored olive oils, rubs, sea salts, loose spices, and much more. Plus, the shop offers a wide variety of samples so you can see exactly how different items can be used!

Special Mention: The Red Roaster Coffee Cafe

Madison Indiana Guide: the Red Roaster
With a gorgeous window view of downtown Madison and the classic hip aesthetic, you’ll feel right at home in the Red Roaster. The coffee was solid and the service friendly, so I could definitely see myself making that my go-to spot in town. They also offer snacks and sandwiches if you’d like something to eat along with your coffee, but I can’t speak to those.

Walk Heritage Trail of Madison

No Madison, Indiana guide would be complete without it! The Heritage Trail of Madison is a 1 1/4 miles concrete trail which connects downtown to the hilltop overlooking the Ohio River (incidentally, a great spot for a snack!). The trail winds along the riverside and offers plenty of benches to relax and take in the view if you need a break.

My favorite bit of the whole walking experience, though, was the railroad incline cut. Head north of the intersection of West Main and McIntire (or just follow the tracks from the concrete portion of the Heritage Trail) and you’ll see the abandoned railroad tracks begin their steep ascent.

Indiana Wine trail

Madison Indiana Guide - Wine Trail
If you’re looking for a slightly less strenuous trail to explore, try the southeast Indiana Wine Trail. There are six wineries altogether but I have to personally highlight Madison Vineyards Estate Winery and B&B. Not only did it have delicious wines, but is also one of only two actual vineyards in the state! (Coming from Virginia, the distinct lack of vineyards is a real bummer.) The other vineyard I’d recommend is the Thomas Family Winery in downtown Madison – so good!

Climb the Milton-Madison Bridge

Head to the far end of the Heritage Trail and you’ll see the powder blue Milton-Madison Bridge stretch over the Ohio River. If you’re feeling adventurous, trudge up the long ramp and head across the pedestrian area of the bridge. You’ll you get a great view of the river; plus, but if you brave the bright sun and head all the way across the bridge you’ll find yourself in Kentucky.

Of course I had to do it! Thanks, Kentucky. I blame you for my sunburn.

Lanier Mansion State Historic Site

Madison Indiana Guide: Lanier Mansion
One of the town’s three National Historic Landmarks, the Lanier Mansion overlooks a luscious garden and the Ohio River. The mansion was built in 1844 for James F.D. Lanier and remains the crown jewel of the Madison historic district. (Tours are $10 – admiring the grounds are free!)

Don’t forget: just across the street is the Visitor’s Center, History Center, and the Madison Railroad Station.

So there’s my Madison, Indiana guide! Are you anywhere close to Madison, Indiana? If so, get yourself there ASAP! If not, you can watch the 1958 Some Came Running which was filmed there and brought Frank Sinatra and Dean Martin to town!

  • This is such a cute little town!!! I love the heritage trail pictures!
    Sara @ Of Golden Roses recently posted…How To Spend a Day in Galveston, TexasMy Profile

  • Vicki Scott

    Next time don’t miss the gourmet cupcakes at The Sweeter Life, 103 east main st.

    • Definitely on the list! Think I need a solid week to get through all the baked goods, chocolate, and ice cream in Madison 🙂 (which I’m totally not complaining about!)
      Polly recently posted…Eat, See, Do: Madison, Indiana GuideMy Profile

  • I moved to Madison earlier this year and you truly hit the nail on the head with this post! Thank you for writing about this quaint little town I now call home 🙂

  • Mike Hoagland

    I was born in Madison , and visit as often as I can. But i havs never looked Better, i love Madison. O by the way i was born in 1947. I now live in Texas about 23 miles north of Dallas.