Most characteristically Democratic state

[King of Kensington]

I voted for Massachusetts.  For me, it's definitely the first state that comes to mind when I think Democratic state.

[King of Kensington]

I answered the question thinking what's the first state that comes to mind when I think Democratic state.  OTOH, if I think of most "representative" of the modern Democratic Party I see the argument for Maryland: high income, socially liberal, and large African American and Jewish populations as well as a good number of suburban Asians (a group that's really shifted Democrat recently).  Plus it's a regional crossroads: the suburbs of Washington seem to be a mix of the suburbs of Atlanta and Philadelphia with a bit of California thrown in.