So the story is, the rail used to run through here to get from Portland to San Francisco but it got rerouted in 1927. And more recently than that the rail lines were used for local deliveries between Talent, Phoenix, Medford and Ashland. Apparently they will be getting started again sometime this year.
For the moment, the Ashland Railroad district is just a handful of city blocks near downtown that happen to be near the railroad. It's the flattest part of the neighborhood which makes sense. It's the most walkable area and has all of the important stores - the Ashland Food Coop, the Hardware Store, and the Grange. You are pretty much covered for anything.
I go by there all the time when I am jogging, there is a great trail that follows the railroad for a while.