When i tried the ruby 200 version i got an error with yajl since jekyll seems to reference the 1.x version but when i build it looks for the 2.x version with ruby 1.9.3 i also get errors because i have utf-8 encodings, so i had to do this to run Jekyll on windows 1) install ruby 1.9.3 2) install ruby devkit 3) install python 2.7.5 4) add python to path 5) gem install jekyll 6) gem uninstall pygments.rb --version "=0.5.2" 7) gem install pygments.rb --version "=0.5.0" 8) chcp 65001 9) jekyll serve --watch 6/7/8 are because i have utf-8 encodings 6 is the actual culprit for the utf-8 problems 3 is because 7 depends on it I'm using Visual Studio too, so i set myself up a quick run command via the "external tools" Title : Jekyll (build && run) Command : cmd.exe Arguments : /K chcp 65001 | jekyll serve --watch Initial directory: $(SolutionDir)