Remain in Play
This is as much a database of commercial games that have been released into public domain as it is a gaming site. It provides info, screenshots and downloads of freeware games, but keep in mind that the database includes not only playable games, but also source code and raw data if those were the only things released to the public. There options to filter games by type of distributed content, and it's a good idea to look for binary executables if you want to get playable games and not files that are barely useful if you aren't a programmer or game developer yourself.
Videogame Music Preservation Foundation
A database of music from video games, regardless of platform. You can browse entries by games, by artists, formats or platforms. Also has its own Wiki.
Theodor Lauppert's Game Gallery (mirror site)
Here you'll find interesting, insightful reviews of games, tons of related links, screenshots, demo/shareware/freeware downloads etc. You can browse games by genre, title, platform (featured games aren't limited to PC only), or country. There are also a few interesting related sites:
King Svatopluk's Court - a nice site dedicated to various RPGs like the Elder Scrolls series.
Svatopluk's Game World - various articles about games.
Svatopluk's DOSBox - a large, unsorted collection of screenshots from various DOS games.
Svatopluk's Arcade - a lot of info and screenshots about all sorts of arcade games.
The Computer Show
This is an archive of previews, reviews, walkthroughs and other articles about games that have been released in the nineties.
Demu (formerly known as DOS Museum)
This is by far the largest archive of shareware episodes, demo versions, extras and utils for DOS and Windows games, as well as a selection of other programmes. Quite a few rare items can be found here, so it's a must see for everyone
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RGB Classic Games
Behind this site is an extensive agenda of preservation of old games (DOS and Windows), and thanks to the initiative of the site's author some old titles have been officially released into public domain by their respective developers following Internet petitions. RGB Classic Games is unique because it aims to include every existing version of each featured game, and the community members actively search for rare releases of old games. Each game on the site is accompanied by an brief but informative description that contains info on developers, publishers, current availability etc. Non-playable content is usually not included. The site also offers their complete collection on DVDs. Links to sites that offer full versions of featured games for purchase are present where applicable. There's also an extensive archive of emulators and other utilities you might need to play the games on modern machines, and comprehensive guides to successfully running old games on new hardware. In addition, there is an option to play featured games right in your browser.
Smush The Cat
A nice collection of shareware episodes, demo versions and freeware full versions of old DOS and Windows games. Descriptions and other info are scarce, but links to official and related websites for games are present if possible. There's an option to browse by multiple categories (platform, game type etc.). The site also offers utilities that might be needed to run the old games on modern systems.
dosgames.com
This is a popular site with a large archive of DOS games, offering playable demo versions and shareware episodes. Well-known classics are present alongside more obscure titles. There's also a community forum where people can get help with getting a game to run on a modern machine, or locating an old game they just can't find. A selection of utilities needed to run the games is also available.
DOS Games Archive
A sister site to dosgames.com. Non-playable content is also present, as are full versions of games that have officially become freeware. There's a multi-category browsing option (by genre, playability etc.), a number of selected screenshots for each game (unfortunately, they're not always from the demo version), cheat code listings and links to places where you can buy the full version if a game is still sold.
The DOS Multiplayer Archives
This site focuses on playing old DOS games over the net (through DOSBox). It offers demos of DOS games that have multiplayer capability, already bundled with DOSBox configured for online play. The collection of games isn't very large at the moment, but it can be expected to grow. Currently, the focus is on the less known games that have a multiplayer option, because they're not as easy to run on modern systems as those well-known classics (Doom, Duke Nukem 3D etc.) that have source ports to newer platforms, as well as large supporting communities.
3D Realms' Master Download Page
Apogee Software, more commonly known as 3D Realms after it's sub-brand focused on 3D games, pioneered the shareware model of game distribution, in which a sizeable portion of a game ("episode") was offered for free download and distribution, and the rest could be ordered by "registering" the game, if the player liked it. This successful strategy was later employed by other companies, like id Software, and the result is a large number of classic shareware games that are freely distributed. The downloads archive features shareware episodes of games published by Apogee/3D Realms, and also offers full versions of games that have become freeware. Generally, the 3D Realms website has a lot interesting stuff to explore, visit their FAQs section and the extensive Apogee Legacy interviews archive by Joe Siegler.
MicroProse FTP Archive at GameFront
This is an archived copy of the official MicroProse FTP. Playable game demos, previews, patches and related files can be found here. The descriptions are rather scarce, insufficient and sometimes misleading though, so in some cases you might not know what you've got before you've actually downloaded an item.
Westwood Studios FTP Archive
An enhanced version of the Westwood FTP, with some extra content thrown in, by Nyerguds, a well-known C&C enthusiast and author of the unofficial C&C v1.06 patch.
The Chaos Regime
A site about games by Bitmap Brothers. Features demo downloads, screenshots and interesting info.
Interplay Official Website
The official website of Interplay Entertainment. They've got tech support for their old games, as well as demos, patches and other extras like PDF manuals and, in some cases, even music (e.g. downloadable MP3s of Descent II CD tracks).