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JTLs Guide to Dining Downtown Madison, IN

Probably the most frequently asked question I get from shoppers is where to go to eat in Madison. So I thought I'd put together a post with a few of my favs. 


THE CRȆPERIE. Our newest breakfast and brunch spot located on Main Street. The Spiced Pear and Walnut is pictured below and so good!

THE ATTIC COFFEE MILL CAFE. The perfect spot for a morning cup of coffee, an afternoon pick me up, or lunch. This has been a go-to spot in Madison for 50 years! Grab a bag of Snickerdoodle coffee on your way out. (My Fav)

ANALOG COFFEE. Another Main Street favorite. The NY Bagels are a must! They are the real deal...chewy crusted bagels. Great place to hang out and relax.

THE RED ROASTER COFFEE & EATERY. A local favorite place to stop in to study, work on your laptop, listen to music, grab a bite to eat, or people watch. 


PIZZA UNCOMMON. Great pizza spot with an extensive menu of uniquely crafted pizzas and they are made entirely from scratch. The sweet grape gorgonzola pizza pictured below is fantastic!

RED PEPPER DELI. Absolutely the BEST deli place in Madison. Great sandwiches, unique side salads, and fresh daily made soups!  Their signature sandwich The Madisonian which is my personal favorite and bow tie pasta is my go-to order every time.

THE DOWNTOWNER. Is a go-to because anyone can find something to order from their menu. I love the Parmesan Pesto Grill. Famous for their giant freshly baked cookies! 


RIVER OAK CHOPHOUSE (NEW) Fantastic steakhouse on Main Street. An upscale vibe, delicious dishes, great atmosphere. Ordering the steak is a must.

RED ON MAIN. Glenn and I's favorite spot for date night. Modern vibe, great food, and great drinks! You can't go wrong with anything on the menu. We've had it all!

MAD LOVE. Great ambiance. Great date night spot located on the West End of town. The Smash Burger is delicious. And you must start off with the Pretzel appetizer. Probably the best I've ever eaten.

OFF BROADWAY TAP ROOM. Great place. The food is delicious and they have THE BEST TACOs... Sweet Potato Taco is amazing! You really can't go wrong with anything on the menu. 

SHIPLEY'S TAVERN. They are known for their burgers. You can't go wrong with a burger and beer. Right?

HINKLE'S. This little iconic diner on Main Street has been a favorite spot since 1933. You can't visit Madison without eating at Hinkle's.

Feel free to add any recommendations in the comments! Tag us if you go to any of our favorite spots. 



  • I visit Madison frequently. I have been to most of those places. My favorites are Red on Main,Mad Love and Red Roaster. I’m looking forward to visiting The Creperie during Ribberfest…. And J Twist of course.

    Diana Paine
  • Love that you started a blog! Couldn’t agree more with the above restaurants. I love our little town!

    Nicole Ford

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