Haven't used trac for a year, but what I remember is that most plugins are available trough subversion and already packed as an egg (which is kind of an installer in the python world, but I am not very familiar with the concept).
Most plugins are available at http://trac-hacks.org/ and the easiest way to install a plugin is
easy_install http://svn.domain.tdl/path/to/plugin/
the folder should contain a setup.py and a setup.cfg file.
easy_install checks the files out from svn and installs the plugin. You can find details here: http://trac.edgewall.org/wiki/TracPlugins
If the plugin makes database changes you have to call
trac-admin upgrade
from console.
http://trac.edgewall.org/wiki/TracAdmin
If I remember right, the install through the webinterface installs the plugin locally (for the instance) while easy_install installs it globally (for all running trac sites) and is the more common way to install a plugin.
Hint: After every plugin install you have to restart trac
Hint2: Most plugins don't tell you how to install and only give a link to the root of their svn. You only have to browse the svn folder and locate the folder containing the setup.py.
The rest is done with easy_install.
Example:
Plugin: http://trac-hacks.org/wiki/GoogleChartPlugin
Wiki pages tells you:
You can check out GoogleChartPlugin from here using Subversion, or browse the source with Trac.
where here
links to http://trac-hacks.org/svn/googlechartplugin/
The svn contains two versions. Browse to http://trac-hacks.org/svn/googlechartplugin/0.11/trunk/ and copy the path.
Then do
easy_install http://trac-hacks.org/svn/googlechartplugin/0.11/trunk/