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Auric's Ultima Moongates has the history of all nine games in an easily read and short form. Fans of the Ultima series may spend some fond moments reading the walkthroughs and looking at the maps of those early games, as well. Sirideain's History of Sosaria is a much more detailed account, for those lorehounds who need it. Sadly, though, it's an unfinished account, yet well written and worth the read.
Underworld Dragon's Notable Ultima is another worthy site to bookmark, in particular the concise CHRONOLOGY of Britannia section. The Ultima Encyclopedia is not exactly a lore site, but many of the listings are lore-related. Alas, it too is in dire need of attention and updating, so if anyone knows Guru Dragon, have him get on that, will you?
So now you've read through the lore, are in game and have your character ready to begin roleplaying. What to do? Well, to help facilitate RP, you should learn how to use emotes, which here is done simply by typing (without quotes) ":[spacebar]<your text>". Your character's speech will be a different color than normal and have an * on both ends. Macros are available for things like bowing and saluting, but the colon method is still the way to go.
Need a quicker way still to hit those emotes on the fly? Then you'll want the mod UO Curse Tool. Only one of few mods officially endorsed by Origin for use with UO, it is THE one to use if you're a roleplayer. Its' primary focus is as an Elizabethian random curse generator, which is a hoot to use own its' own. It also has 24 slots where you may type in text to Say, Yell, Emote, Whisper, and Gesture. Additionally, UO Curse Tool can be programmed for use with 30 characters, or you may use all 30 profiles for one character if you wish, increasing the number of slots available to 720. Either way, it is a very handy mod for UO roleplayers.
On the topic of language, I earlier mentioned that Elizabethan speech is an acceptable form in UO. The NPCs use it often, albeit in a mild way, so players not used to reading Shakespeare may still understand them. If you'd like your character to speak in line with the spirit of the game, then check out this Elizabethan Language website that includes an online dictionary and an Elizabethan Era Index. Also found here is my favorite Elizabethan Insults Dictionary, with phrases taken directly from the works of Shakespeare, and can be easily copied and pasted right into the UO Curse Tool. Huzzah!
The Ultima Web Archive is another language source I use. For one, it has an easy graph of the Druidic Runes that can be found throughout the entire series of Ultima games. Secondly, it has a primer on Gargish, the language of the gargoyles, which is sure to become of much greater importance hopefully in the near future.
Meeting fellow roleplayers may be of importance to you, and for that, the Ultimate Online Forums is one place to go. Here you'll find helpful sections for UO Events, UO Roleplaying, and UO Guilds & Player Run Towns.
Another premier website that has long been associated with Ultima Online is UO Stratics. Containing an unmatched quantity of UO related information, UO Stratics may well become your most visited site for everything UO. It's particularly useful for keeping tabs on specific events upcoming for whatever shard you decide to play on. Aside from the forums for each individual shard, the UO White Stag Inn forum is where to go to find more of UO's RP community.
With an eye toward the future of UO roleplaying, I am anxiously awaiting the release of Ultima Online - Stygian Abyss, which will open the race of gargoyles to players. If you know the part gargoyles have played in UO lore, then you may be as excited as I am to see and take on the challenge of roleplaying them in game. As far as I am aware, no other MMORPG has gargoyles, and that alone is worth a look to me.
Ultima Online is where I began to manipulate all the RP skills acquired from years of tabletop gaming into computer gaming. Why do I still play UO after all these years, when I'm surrounded by MMORPGs that are widely considered to be more mainstream and current with today's technology? Because there is still an element of roleplaying in UO that I have yet to find in any other MMORPG. I play no other game that has in game towns created and maintained by solid roleplayers. Call it nostalgia, call it faithfulness, or what you will. I know I have fun, and that's what it's all about. Join me, and I bet you'd have fun as well. Role on!