Today I discovered that one can customize session restoration in Terminal.app by defining the shell_session_save_user_state function. Here is a script that restores active virtualenv, e.g. after you reboot your machine: https://gist.github.com/Kentzo/185e4eab382bbcf1f0a9738a28128dce It's written for ZSH, but it's fairly simple to port it to bash: you don't even need plugin, since session management is supported out of the box. Here is a plugin for oh-my-zsh: https://github.com/Kentzo/oh-my-zsh/tree/master/plugins/session