Ok, I have to comment on this thread, because I'm surprised no one mentioned this strain of thought.
As a disclaimer, I was three years old when I realized that other music and bands existed besides Jerry Garcia. I remember the moment, that other people who played music actually had bands that sold tapes to put into the cassette player and had concerts, it was quite the epiphany. I just thought there was one band, and that was the grateful dead, and that's all anyone on the planet ever listened too. So this is coming from someone who was raised from the beginning with the imagery coming from these songs pretty much exclusively.
As a child, I always associated this song with death. I always saw a beautiful young girl, ribbons in her hair, either sick or passed away. As I got older, I always heard the line "one pane of glass in the window, no one is complaining though, come in and shut the door" as a led reference, you know, one pane out of four, but no one is complaining and c'mon shut the door is meaningful on a few levels. Learning about the patterns of the scene and the influence of and politics behind lsd on the scene and the band, it just made it more meaningful to me. I don't know how to put a lot of this into words, and probably shouldn't, but there is a reason so many folks through the 60's and 70's told me that acid wasn't the same as it used to be. It wasn't, and isn't. If you take the roller coaster that is the inside world of lsd production, distribution, and politics, you'll suddenly see the lyrics of the grateful dead in a whole new interpretive metaphoric way. It's like they followed what was going on within they're circus and reflected it through metaphors, perhaps not always even consciously . When this song was written, it was the beginning of the end. The 80's saw a massive explosion of availability for everyone to get high, the drug itself being a big draw, but with that the quality and consciousness of the actual molecule deteriorated. The ribbons faded, the 60's died. Owsley left the country. The government infiltrated a tight lipped community and eventually took control. (uncle sam, that's who I am, been hiding out in a rock n roll band--HA) But through all that, the family held together, they're was a love some would never leave. I always saw annie as this young beautiful icon of the 60's, ribbons in her hair, and Hunter admitting the death of what he knew was now a time past, 10 years, ships at sea, if I told another what your own lips told to me, I know so many who did 10 years on a life sentence for selling the reference right after to keeping your mouth shut is hard for me to hear any other metaphor. I saw the whole song one night after making certain discoveries about l.s.d's history and certain messages I had already heard in other lyrics. I saw things about the song that I knew I couldn't really express in words, but knew positively that it was very much about what was going on at the time, expressed in Hunter's past-timey metaphoric dreamscape world. I do still like others interpretations of it however, as the song does evoke a feeling of long-ago times. If I didn't feel so darned paranoid about the idea, and also think that maybe some things should stay out of public knowledge, it would be fun to write a whole dissertation on the subject of LSD history through Grateful Dead song lyrics. It really makes too much sense. Especially when you get deeper into it.