When comparing Middleman vs Wintersmith, the Slant community recommends Middleman for most people. In the question“What are the best static site generators?” Middleman is ranked 4th while Wintersmith is ranked 5th. The most important reason people chose Middleman is:
[Minification and compression](http://middlemanapp.com/advanced/file-size-optimization/index.html) are as easy as setting a few configuration options, and [unique asset hashes](http://middlemanapp.com/advanced/improving-cacheability/) are available to allow you to invalidate the cache of files that change regularly.
Ranked in these QuestionsQuestion Ranking
Pro Support for a variety of templating languages and preprocessors
Middleman supports lots of compiled languages, such as Less, Markdown, Textile, CoffeeScript, Stylus and more.
Pro Extensible and flexible
Middleman has a resources page full of official and community extensions.
Pro External pipeline management with Webpack
Replace your Gulp, Grunt, Bower configs
Pro Embraces Rails conventions
Middleman follows established conventions so if you know rails, you can easily pick up middleman.
Pro Easy deployment options
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 Too much magic happens
For new users it is hard to understand what is going on and why.
Con A little more complicated than other static site generators
Middleman is a big piece of software, it's not simply a static blog generator. Because of all the functionality and flexibility it offers it can be a little more complex than other static site generators and a little harder to learn all of its bells and whistles.
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.