General Gaming and Simulation
About.com's Boardgame Site is a good place to start.
Mark Bakke's Night Owl Mk. II hosts Boulder Games and has an ecletic collection of material, including a wargamers' home page list.
The name could be better, but BoardGameGeek is an indispensible site for gamers.
There are many decent chess sites on the web. Chess-poster is pretty good.
ConsimWorld focuses on breaking wargame news and discussion.
Internet pioneer Delphi is still around hosting forums. This links to the Table Top Sports forum.
The Escapist is a role-playing game advocacy group.
The Library Game Lab of Syracuse studies the role of games in libraries. It also offers a free online course on the topic.
GAMA publishes Games in Education, a pamphlet series on classroom gaming, and has other programs for teachers, including a Google Group.
The Game Publishers Association is an association of small game companies. It also sponsors The GPA Ring.
Game Theory.net studies that topic.
Rick Heli's site has extensive game bibliographies, design links, and ludographies.
HMGS is the major miniatures gaming organization.
History of Games is a decent bibliography of writings on the subject.
The Maxwell Air University's Library has an extensive listing of professional wargames.
The Military History and Wargamer's Web Ring unites military historians, wargamers, and hobbyists.
The Motley Fool offers many articles on games.
The Online Guide to Traditional Games offers a lot of information on many old favorites.
Pastimes and Paradigms is an online game history exhibit.
Brian Phillips's home page has a massive collection of gaming links.
Vitas Povilaitis also has extensive game links and materials.
RPGnet hosts back issues of Games & Education, including my article on classroom gaming. It is also the definitive role-playing game site.
Brian Train's designs usually study insurgencies.
The U.S. Army War College offers a wargame bibliography.
Tom Vasel reviews lots of games, and has an interview series with designers and publishers.
The Wargamer's Ring is the largest conflict simulation webring.
Web-Grognards is the major source of wargame information on the Web. It includes The Battle for Moscow, First Blood: Guadacanal, and links to many other freeware games.
Yahoo has thousands of Groups devoted to games. Especially useful are the BoardGameDesign, boardwargaming, rpg-create, Simulating War, Spielfrieks, and wargame-creators Groups.
Game Design and Marketing
The Boardgame Designers Forum is pretty much what the name implies.
James F. Dunnigan's The Complete Wargames Handbook contains extensive information on wargame history, game design, and his career. Also worth visiting is his homepage.
EDTEC 670. Materials for a game design course at San Diego State University.
Alan Emrich's site includes materials for his Principles of Game Design course taught at The University of California-Irvine. The site includes freeware versions of Napoleon at Waterloo and Strike Force One.
The Game Crafter is a print on demand firm for games.
Game Design Central is aimed at those designing for general audiences.
Games Concepts studies game mechanics.
The IGDA is a professional association for game developers.
Invisible-City is a game design collaborative.
Tom Jolly's site includes information on game marketing.
George Phillies and Tom Vasel have written two books on game design. Available here.
Reacting to the Past is a consortium of colleges developing educational games.
rec.games.design's FAQ is a good place for a beginner to start.
Ready to start your own game company? Read Steve Cole's Running a Game Publishing Company first.
Philip Sabin's site includes information on his book and his and his students' designs.
Sloperama Productions has information on the business side of gaming.
Game Media
Board Game Studies is an academic journal on game history and design.
Countermoves is an online wargame zine.
The Diplomatic Pouch is the best online Diplomacy zine.
The Game Cabinet focuses on European games.
Game Studies is a web journal devoted to computer game research.
The Games for Educators site has newsletters for teachers.
The Games Journal is a monthly boardgaming e-zine.
iSimulacrum offers support for the game collecting journal of that name, a wargame database, and counter scans.
The Miniatures Page is the best online zine on the subject.
NASAGA publishes Simulation & Gaming, the most important academic journal on the subject.
Paxsims is a blog on historical simulation.
Lewis Pulsipher offers Sweep of History Games Magazine as well as articles on game design and his own work. Teach Game Design is his blog on the subject.
Terra Nova is a weblog focusing on MMORPGs.
Training and Simulation Journal covers military gaming and simulation.
James Werbaneth’s OnLine of Departure offers support, including computer freeware, for the print magazine.
Online and Freeware Games
Ancients has been upgraded but the old version is still here.
The Black Plague Simulation is aimed at the middle school level.
The British Go Association offers downloadable versions and online play.
Louis Coatney's home page includes the free 1st Alamein, Leyte Gulf, Moscow Attacked!, Moscow Defended, The Russian Portfolio, Stalingrad Attacked! and War Against Russia, along with game design articles and naval modeling information. His History site includes The Gazala Gallop and his classic German Eagle vs. Russian Bear. Now that he is retired, he is posting free games at a stunning pace.
Crisis at Fort Sumter is an interesting simulation of the Civil War's start.
Educational Freeware lists and reviews free online materials for teachers.
Run by the Department of Education, the Educational Resources Information Center has educational games and materials, usually for free.
Free At Last simulates the civil rights movement.
Freewargamerules collects free miniatures rules.
History Lessons for Junior Generals has numerous simulations for the lower grades.
David Kershaw has several free historical games on his site.
John Kim has links to over 500 free RPGs on the web. There is a lot of information on RPGs here, including a games and education page.
Lloyd Krassner's Warp Spawn Games site has over 420 of his games and variants.
Learning Vocabulary Can be Fun is aimed at lower grades.
Mancala is one of the oldest games in the world. Play it here.
MicroTactix's PlainLabel Game System can be used for a variety of RPG and miniatures projects.
Like puzzles? Try this site.
Garry Stevens' site has several historical games, mainly involving the British monarchy.
Sudoku is this the latest puzzle craze. Try this site for starters.
Tabletop Sports offers sport game downloads, including Extra Innings.
Computer
Many of CompuServe's legendary forums are now open to the public.
The Electronic Frontier Foundation is protecting your rights on the Internet.
FTP Explorer--an FTP program free for educational users.
The Free Site--a good source of computer freeware.
Freeware Home has a wide selection of educational games.
FreeZip--a nifty zip/unzip program.
Google Groups is the place to find and search Usenet groups devoted to games. Now owned by Google.
The Internet Archive is a library of internet history.
Lycos is a network of interesting sites, including Wired.
Tired of Firefox and MSIE? Try Opera.
Reading
Citizendium is another open source encyclopedia, but more regulated than Wikipedia.
eFanzines hosts online science ficition magazines.
The Journal of Electronic Publishing covers numerous topics of interest to Internet publishers.
LivingInternet offers a concise introduction to Internet history.
Project Gutenberg is a great source for free ebooks.
Space.com covers space exploration news thoroughly.
Wikipedia is an online encyclopedia being constructed by the open source process.
Local
Arisia is the largest science-fiction convention in New England.
Battleground Games has two South Shore sites.
BattleGroup Boston is the best miniatures club in Massachusetts and sponsors Havoc, an annual convention.
Boskone is hosted by the New England Science Fiction Association.
It is not San Diego but Boston Comic Con is massive.
Friendly Neighborhood Comics in Bellingham hosts several monthly game events.
Harry's Hobbies. Besides a store, he also sponsors collectors' shows. Never know what you will find.
New England Comics. Mainly comics but also strong in game material.
Newbury Comics. Mostly music but lots of games too.
On the Stack Games in Norwood offers lots of events.
TotalCon is a major eastern Massachusetts game convention. All genres.
Unity Games is the largest umbrella organization for New England gamers.
Vericon is a nice college con.