This almost didn’t happen, but luck would have it, I had some time to drive around Deadwood while the little man napped in his car seat.
My observations:

First impression of course was that it was a lot like Cripple Creek, Colorado. A lot of old historic building transformed into casinos. The first pass through on the highway left a lot to be desired as the highway bisected the town to move cars faster, turning the butt end of many building to the road.

The canyon effect was as expected, however Deadwood is graced with having a relatively flat Main Street in contrast to Cripple Creek which boasts many unnavigable hills by foot (at least for the demographic frequenting the casinos). Flat = Big Plus for retail as discussed in the blog post: Slope and How it Affects Walk Appeal

The old vs new architecture was very evident, although Deadwood has attempted with seemingly codes and guidelines to fit new architecture with the old, the execution of the details was not there.

The brick streets were a nice touch, as was the absence of paint on the brick, however the width if the street was still too wide, especially considering on-street parking is prohibited with many, many signs.

The town was also broken up, divided by the highway, in what appeared to be the tourism side and the resident side. Although the resident side had some nice old houses and brick streets, there really wasn’t anything special about it. It seemed that the tax proceeds went straight back to the tourism side, which is unfortunately common.