If you look here: http://en.wikipedia.org/wiki/Stack_Overflow
You\'ll notice there\'s a little \"Content\" section, if you click on one of the links, it will send you to
One possible (semi-automated) solution is Eugene Kalinin's github-markdown-toc. This tool essentially crunches through your README.md file and snarfs out #'s headings to create a TOC.
Feed your README.md to the script (as noted in Eugene's README.md)
cat README.md | bash github-markdown-toc
Cut and paste generated TOC and place it at the top of your README.md file
Note that this bash implementation only works on Linux (from what I can tell).
As a side note, there is a golang implementation and is probably more of a hassle to get working.