pigeons.net
An excellent site lots of freeware in lots of categories. They also have mp3s, all types of free internet services, a Java/CGI section, and lots, lots, more! 

Nonags
NONAGS lists only the Best freeware and No-Nagged shareware. Thoroughly rated and reviewed (using the "ducky" system). (Win95/98/NT) 

Freeware Home
A fantastic freeware site with lots (and lots) of freeware for Win95/98/NT. They seem to list some freeware that is not listed on other sites (Such as some educational software). 

FreewareFiles.com
An excellent freeware resource that's just packed with goodies. They have tons of freeware for Win95/98/NT and a Win3.xx section. They also have a drivers section, libraries section, and much, much, more! Go there. 

Kids Freeware
A great new site with lots of free software and free services for kids. This site has games, themes, screen savers and more. From toddlers to grown-ups, this site has something for everyone.