I've been playing Dungeons & Dragons and other pen-and-paper role-playing games since I was in grade school, and I've been using Apple's Macintosh computers at least as long. Thirty years later, both RPGs and Apple computers are still a part of my life, only now I'm use Macs in every aspect of my game, from writing the adventure to tracking combat to maintaining my web site.
I'm always looking for Web sites to add to this page. If you have one, email me at email@example.com.
About My Macs
The Computer: A Mac Book Pro (2.2 GHz Intel Core 2 Duo) running Mac OS 10.7.x Lion. This is my aging workhorse machine; it's served me well, but it's about due for a replacement
The Tablet: A iPad 2 (16 GB). Used to read game PDFs, run modules at the table, control playlists on my Mac, and jot down notes.
The iPod: An iPhone 5S (32 GB). Most often used to roll for critical fumbles and critical hits using Paizo's iOS apps.
Mac RPG Utilities
The GURPS Character Sheet is a Java-based tool for creating characters under GURPS 4th Edition rules. It has all the skills and spells you'll need to create characters, and does most of the heavy number crunching for you. It's written in Java and will run equally well on Windows, Mac or Unix operating systems.
Originally a Windows-only tool, Hero Lab is now available for Mac as well. It's popular with my gaming group because it supports some of our favorite RPGs, including Pathfinder, Savage Worlds, Call of Cthulhu, Mutants & Masterminds, d20 System, 4th Edition, and World of Darkness. The drawback is its printing; the default character sheet templates are limiting, and don't organize things as well as your typical print character sheet. Still it's a worthwhile investiment if you have complicated character concepts or need to throw together quick-and-dirty non-player characters for your campaign.
Mac game masters who need a program to detail the lands and dungeons of their campaign world should check out RPG MapMaker, a Mac-only, OS X-native mapping program. Among the program's many features are the ability to create a variety of grids, random maze and terrain generators, terrain tiles, and a terrain editor.
Generic RPG Utilities
A robust Java-based mapping tool for creating dungeon maps. You can use it to create battle maps, one-page dungeons, and even random dungeons ... complete wiht room descriptions! It's a companion tool to Hexographer.
I want to run an old-school Greyhawk campaign just to use this tool. As the name implies, Hexographer is all about making hex-based maps, like the classic World of Greyhawk map or the expansive Wilderlands of High Fantasy map set. It's a Java-based tool that's available for free online, and offline as part of a premium download. I've played around with the online version had some fun with it; when I have a project that demands hex maps I'll buy the premium edition. It's a companion tool to Dungeonographer.
PC Gen is a Java-based, open-source character generator that incorporates the D&D 3.5 core rules, as well as numerous d20 game systems and supplements. Because it is Java-based, it can be run on Mac, Windows and Linux operating systems.
I used PC Gen a lot during my d20 days, but it eventually fell by the wayside as Excel-based spreadsheets like HeroForge rose to the fore. The tool's great strength is its support for a wide variety of d20 rule sets; the greatest weakness is its often-clunky interface.
RPTools offers a suite of Java-based programs to enhance your role-playing game sessions. MapTool is used to create an online game table (though I've heard of folks who project its maps in their game room for local play). TokenTool is used to make tokens for digital battlemaps, while InitiativeTool helps keep track of combat. It also has tools for character management and dice rolling.
A Java-based tool for playing board and card games online that is available with a Mac installer. There are a tremendous number of modules for the game including a variety of war games, Arkham Horror, Battlestar Galactica, Axis and Allies, and many, many more.
Mac Gaming Web Sites
News and previews about games and gaming-related hardware for the Macintosh. There are also online forums, desktop themes, and a files section where you can download the latest Mac demos.
Character sheets for 25+ gaming systems, including Dungeons & Dragons, Arcana Unearthed, Spycraft, Gamma World, Call of Cthulhu, and Traveller. All of the sheets are downloadable in Adobe Acrobat format, and were created on a Mac.
Sean Reynolds is a prolific RPG writer who created a bunch of excellent source books for Greyhawk and the Forgotten Realms. He has Excel spreadsheets for generating gear, magical staffs and magical weapons. Of particular interest to Mac fans -- especially older ones -- are his HyperCard stacks. They are created for Apple's Hypercard, a database program that used to ship on old Macs, and which is all but extinct now.