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I tried Octopress, but didn't like the default theme/layout — I wanted to design my own theme, and was hoping to build up a site from scratch, not rip out what was already there. After considering a bunch of Python-based SSGs which didn't impress me for various reasons, I went with Jekyll and have been quite happy.

One feature on my todo list is to find a way to add infinite scrolling (this is 2012, I don't think blogs should have “Next Page” anymore!). It seems it shouldn't be too hard but a quick search suggests nobody has tried this with Jekyll (or Octopress) yet.

What Python-based SSGs?

I looked at Hyde, Cactus and Pelican, but confess I can't recall what I didn't like about the first two. Nothing seems obviously wrong with them. Maybe they looked unmaintained or not as mature as Jekyll, although Cactus has a bunch of recent commits so that doesn't seem right. With Pelican I was scared off when I saw the license (Affero GPL, which forces you to provide source if you use the code on a live site, or something like that).

Sorry this isn't a more useful comparison. I wanted to find a good-enough SSG quickly, so my search was pretty shallow.

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