What is this?

This is just a short guide on how to run Ultima Online on Mac OS 10.11+

Other versions of Mac might work just as well, but are not tested by me.

Installation

Run each of the following commands in the given order:

ruby -e "$(curl -fsSL https://raw.githubusercontent.com/Homebrew/install/master/install)"
brew doctor
brew update
brew upgrade
brew tap caskroom/cask

I only had these installed, but Mac OS X Developer Tools should work just as well.

brew tap homebrew/versions
brew install gcc48

This will prompt you for your user password. It might take a while to install.

brew cask install xquartz

brew install wine
brew install winetricks
winetricks corefonts
winetricks vcrun6
winetricks dotnet20
winetricks fontfix

You need to download the installation files of your desired UO version.

For the purpose of this guide I'm downloading Mondain's Legacy in the ~/Downloads dir:

cd ~/Downloads && curl -O http://largedownloads.ea.com/pub/uo/setup-1.46.0.3.exe

Once the download is complete, you can install UO by running:

wine ~/Downloads/setup-1.46.0.3.exe

Follow the instructions you get from the installation, and you should be set!

Running the game:

wine ~/.wine/drive_c/Program\ Files/Ultima\ Online\ 2D/uo.exe