Chocolatey is a free command-line application that tries to make it easier to obtain, install, and update software, especially for developers. See all software reviews.
Installing a new piece of software is something most Windows users can do easily, but before you can step through the familiar "next-next-next-finish" setup wizard interface, you need to get the installer first, and that can be tricky.
Also, once you've already installed an application, updates have to be done on a per-application basis, each with its own unique mechanism.
There's a problem every modern operating system has had to contend with: Linux with its rpm and apt-get package management systems, Mac OS X with its App Store, and Windows with... well, nothing really, at least until Windows 8 and the new Windows Store become mainstream.
If you are setting up a new computer and want to install software in bulk, Ninite may be the best way to do this. But if you're looking for a geek-friendly way to install individual tools and developer environments, Chocolatey is a good bet. Inspired by apt-get, it provides a simple, uniform command-line interface for installing thousands of different packages.
To install Notepad++, for example, you need only open a console window and type "cinst notepadplusplus." Chocolatey will download the latest version of Notepad++ and install it for you, no Next-Next-Next required. If you use UAC (User Account Control, the default privilege elevation mechanism Windows has been using since Vista), you will have to click through just a single UAC prompt.
But how were you supposed to know you can type "notepadplusplus"? This is where Chocolatey's Web-based package repository comes in.
The repository currently features over 400 packages, ranging from the obscure (Fantom, a programming language) to the mainstream (Skype, VLC, and more). This easy-to-search repository is not the only source for Chocolatey packages: Chocolatey uses NuGet, an open-source package manager created by Microsoft. NuGet has its own repository, called NuGet Gallery, which hosts no less than 8,300 unique packages. These are all aimed at developers, though, so you won't find VLC there.
If you don't feel like leaving the console to find out what packages are available, you can just type "chocolatey list" to get a long list of packages available from the official Chocolatey feed. If you're just wondering whether Dropbox is available, for example, you can type "chocolatey list dropbox" and find out a moment later (it is).
Chocolatey packages for applications like Notepad++ don't contain the installer itself. Rather, they go online and download an installer, just like you would. This saves package developers from dealing with software distribution license issues. When it's time to update your software, you can just type "chocolatey update notepadplusplus" (or any other package), and Chocolatey will go online again and get a new installer if one is available.
Chocolatey can't interface yet with the Windows Store to install Modern UI Style (formerly known as Metro) apps. This may not be a serious problem, though, since the Windows Store was meant to solve almost the same problem (making software easier to find and install).
Other than this limitation, it worked well when I tested it, and offers a fast, geeky way to install and update software.