Dominic Deegan: Oracle for Hire - great artwork and nice storytelling, even if it is a little heavy with puns.
Elf Only Inn - It may be dead, but it's still a highly recommended read.
Children At Play - it's got monkeys. Haven-chu always wanted a monKEY?
Pimpette and Associates - I want a morphing snakey-ferret-cat thingy from hell too.
Station V3 - kinda like DS9, except with not as much traffic. And not Star Trek.
The Mansion of E
VG Cats - kinda like Penny Arcade, except with cats, so it's cuter, and without all the extra reading, so it's funnier.
Blambot - free and custom comic fonts for the penmanship-challenged like myself.
University of Massachusetts - Thee my alma mater, I'll cherish for all time.
UMass Minuteman Marching Band - the Power and Class of New England! One of the best marching bands in the country (partly because I was in it *LOL*...that and we won the Sudler Trophy in 1998).
Boston Red Sox - 2004 World Series Champions. And we will never let you forget that.
New England Patriots - excuse me, that's "Superbowl Champion" New England Patriots.
The Simpsons - Best television show...ever.
Futurama - Second best television show. Though the official site is kinda lame, some more fan sites can be found here.
Da Vinci's Notebook - first heard them on The Bob and Tom Show. A male a capella group with great funny songs.
Something Awful - Bringing you the worst of the Internet and beyond.
X-Entertainment - one young man's articles about whatever he fancies...which is mostly 80's nostalgia.
Homestar Runner - Really funny Flash toons. Too many good ones to recommmend anything specific, so do like I did and watch everything.
Higgins Armory Museum - features suits of armor, medival weapons, all kinds of neat stuff like that. It's the only museum of its kind on the Eastern Seaboard, or the Western Hemisphere, or something like that. It's unique, neat, and my brother works there part-time.
Higgins Sword Guild - A group affiliated with the museum (and which my brother's also a part of) that dedicates its time to study the acutal ye-olde-tyme combat manuals, and to perform demonstrations.
The Quotes Database - taken from IRC chat sessions.
Newgrounds - Flash movies and games and such.
Yohoho! Puzzle Pirates - Yarr! I be sailin' the Midnight Ocean under the name LZorro, ye scurvy bilge rats!