Running Jekyll on Windows

Static blog generators have become very popular recently and with good reason. They are simple without any of the bulk of Wordpress or Blogger and they allow you to host it using providers that don't have any ??server side language. One of the more popular generators is Jekyll. Partly because it is used by GitHub, which just so happens to be place most people host them. There is just one problem with Jekyll though. It can be a little tricky to get it working on Windows. This post will hopefully help you solve this.

I've highlighted any gotchas in bold

Part One: Installing Ruby

Jekyll is a ruby application so thats your first problem. It requires you to install both Ruby and the DevKit on your machine. If you haven't already come across it I highly recommend you use chocolatey to do this. Its a machine package manager for windows, kind of like apt for Linux. Its so good infact I rarely setup a machine with out it.

To install chocolatey either go to their website or open up Command Prompt and type:

PS> @powershell -NoProfile -ExecutionPolicy unrestricted -Command "iex ((new-object net.webclient).DownloadString(''))" && SET PATH=%PATH%;%systemdrive%\chocolatey\bin - See more at:

Once this is done you can then go ahead and install Ruby and the DevKit.

You have to be careful at this point as Jekyll runs on version 1.9 NOT 2.0.

So go ahead and use cinst:

PS> cinst ruby -Version


PS> cinst ruby.devkit.ruby193

Part Two: Installing Python

Why Python? You need it if you want to use pygments which is the library Jekyll uses for syntax highlighting. Python 3.* can cause some problems with Jekyll so unless you planning on using it for anything else you're best sticking to 2.7. So again using cinst:

PS> cinst python -Version 2.7.5

Next you need to add python to your PATH enviroment variable:

Open up Control Panel and click on "System":


Click on "Advanced system settings" and then click on "Enviroment Variables..." (Why the Ellipsis?)


Then you need to add the path that you installed Python to, to the Path variable. Most likely, if you used Chocolatey, this will mean adding


Make sure your variables are delimited by a semi-colon.

Now the next bit might catch you out.

Make sure to close all instances of Command Prompt (or Powershell) and reopen them so your Path variable can be reloaded.

Part Three: Installing Jekyll

Now we are already to go-ahead and install Jekyll:

PS> gem install jekyll

This will install Jekyll and all its dependencies. At this point it may work for you, however for me I still had problems with the pygments.rb gem. At the time I wrote this it didn't work for me. At the time of writing it was at version 0.5.3.

If at this point Jekyll still doesn't work it you may need to revert to pygments.rb version 0.5.0. To do this

PS> gem uinstall pygments -v 0.5.3
PS> gem install pygments -v 0.5.0

Part Four: Create your Blog

For this section I'm going to refer you to the official site. Come back when you're done.

Part Five: Hosting on GitHub

You've got two options here. A simple one and a more complicated one. I'll show you the simple way first and then if you need it you can move onto the more complicated option.

GitHub allow you to host a website in one of your repositories at the URL To set this up you need to create a repository called You can then push your newly created blog straight to this repository. The reason you can do this is because GitHub will actually run your application through Jekyll on the server.

Your blog should have a .gitignore file in the root of your blog that contains the following


However, after you've been playing with Jekyll for a while, you probably want to install some plugins. This is where GitHub falls down. It runs Jekyll in safe mode so it will ignore any plugins you install. So you're going to have to start generating the site locally and pushing the compiled site to GitHub. I'm sure there a a couple of ways to do this, but here is my way.

Go to your repository and create a new branch. Call it source.

And set it as your default branch. This is so when somebody comes to your git repository they will see this rather than the compiled site.

Then create a new file in the route of your blog and call it rake.rb and add the following code:

require 'rubygems'
require 'jekyll'
require 'tmpdir'

# Change your GitHub reponame
GITHUB_REPONAME = "<your git repository>"
TEMP_DIRECTORY = "<absolute path location to generate your site to>"

desc "Generate blog files"
task :generate do
  system "Jekyll build --source . --destination _site"

desc "Generate and publish blog to gh-pages"
task :publish => [:generate] do
  system "mkdir \"#{TEMP_DIRECTORY}\""
  cp_r "_site/.", TEMP_DIRECTORY
  system "git init"
  system "git add ."
  message = "Site updated at #{}"
  system "git commit -m \"#{message}\""
  system "git remote add origin{GITHUB_REPONAME}.git"
  system "git push origin master --force"

This Ruby is a ruby rake file, if you want to learn more about it checkout this site. It will give you two commands that you can run from the root of you blog

PS> rake generate

That will generate the site and

PS> rake publish

That will generate your site (locally) and copy it into a temporay location (I usually put it in C:\temp\generate_blog) and push it to the master branch of your git repository.

The master branch is the one github uses for your site

And thats it! Hopefully this will help people where I got stuck. If you have any problems leave a comment and I will try my best to help.