I’ve recently started taking a look at Chocolatey – “apt-get for Windows” – and here are a couple of how-to’s…

Install Chocolatey on Windows 10 64-bit

First off, you might want to know why I’m not using the built-in OneGet, which is a “package manager manager” [sic]?
Well, it turns out there’s no good way of upgrading an installed package using e.g. Chocolatey via OneGet. Duh. Keep an eye on this github issue: https://github.com/OneGet/oneget/issues/6

The most up to date instructions should be available over at https://chocolatey.org and I installed via an elevated command prompt (cmd.exe).

Install Python

Check for latest version available via Chocolatey:

choco list python2

Check for specific version:

choco list python2 --allversions

Install specific version and into custom location using install arguments:

choco install python2 --version=2.7.10 -y -o -ia "'/qn /norestart ALLUSERS=1 TARGETDIR=C:\Python27'"

List all Chocolatey-installed packages:

choco list --localonly

Update to latest version:

choco upgrade python2 -y

…or upgrade to specific version:

choco upgrade python2 --version=2.7.11 -y