We were at Old Market back in 2012 on our first trip driving to South Dakota. I was also there for a bit in the 90s during my college days. I hope to get back more often, as this is just a very cool and fun to explore area.
There are several unique shops, local restaurants, and fun people in general. Old Market is several blocks of attractive old buildings well maintained and restored that are vibrant and exciting.
Its a great place to people watch and walk. Also, for a bigger city, getting there (and getting around Omaha) is pretty simple. Sure, its a bigger city, but it has an unrushed, friendly vibe. Its not a terrible hassle to navigate.
I remember visiting in the 90s and going in to a record shop. That record shop didn't have what I was looking for, but the staff tipped me off to another shop that did!
There are still cool music shops here. There were some interesting collector shops too. One store had vintage toys (it was kind of an antique toy mall) and they had a huge main floor and basement. You could shop there all day!
I found a great bookstore (more on that later) and we had a nice meal.
I believe most of the hotels in the area offer shuttle service to and from Old Market (ours did).
Here are some photos, but google around about Old Market some more. it is a very unique place.
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