When comparing Octopress vs Wintersmith, the Slant community recommends Wintersmith for most people. In the question“What are the best static site generators?” Wintersmith is ranked 4th while Octopress is ranked 6th. The most important reason people chose Wintersmith is:
Wintersmith has an extensive Markdown support. Default, it is rendered by [Marked](https://github.com/chjj/marked). However there are plugins available for [others](https://github.com/jnordberg/wintersmith/wiki/Plugins) (such as [Markdown-it](https://github.com/dwaite/wintersmith-markdown-it)).
Ranked in these QuestionsQuestion Ranking
Pro Very easy to use
Octopress is designed to remove all the time-consuming and frustrating tasks you usually have to deal with when using Jekyll. You don't have to write your own HTML templates or do any configuration to get started. The default template also takes care of any basic CSS/JS you need to write to get going.
Pro Lots of plugins (from Jekyll + 3rd party)
Another advantage of being based on Jekyll is default access to the extensive plugin system for Jekyll. There are also plugins developed specifically for Octopress.
Pro Based on Jekyll
As Octopress is simply a framework on top of Jekyll, it benefits from being based on one of the most popular site generators available. The primary benefit is that it is backed by git and is built in such a way that the site can be easily re-generated if the content changes.
Pro Uses Markdown for writing
Uses the Markdown syntax for writing blogs.
Templating engine comes with Jade plugin and many third-party plugins.
Pro Very flexible
Wintersmith only has a predefined directory structure, everything else can built any way you want.
Pro Built on node.js
Node.js is a software platform for scalable server-side and networking applications.
Con Not Actively Developed
Last commit is Feb 22, 2016, Social media hasn't been updated. Dead project?
Adding a new post, for example, causes the entire blog to be regenerated.
Con Some plugins have hard-coded values
Con Not as flexible as Jekyll
Con Code and data are intertwined
Con Thin and disorganized documentation
The documentation for Wintersmith is lacking examples and clear explanations. It's also quite disorganized, making it difficult to find what you're looking for.