While all of these games can be made to play, their "historic" nature means this is not always easy.  In other words, software written in the 80's may have problems running on Windows 10.  Even the popular "DOSBox" emulator, often used to run such old software, is getting pretty old itself - last updated in 2010.  Still, if you're curious enough, a full virtual machine running Windows 95 will probably play any game that doesn't play directly.  Good Luck!

Visual Pinball	This pinball emulator runs hundreds of pre-built pinball games. It also lets you edit games or even build your own.	This is not exactly a simple setup, but it’s worthwhile if you like pinball. Some tables can be found: here.
Zork Trilogy	These are classic “Interactive Fiction” text-based games where you type in commands to affect the plot of a story that has you as the lead character.	From a time before PC graphics were game-worthy: the 1980s. In fact, some original Infocom games are now valuable collectors items.  If this type of game catches your interest, start by reading about Z-machine.
Icy Tower	A simple but challenging climbing/platform game. Since it has no level breaks, you just keep playing until you lose.	Freelunch Design produced a bunch of other interesting games too, but alas, they have closed.  The link is to a fan site that still has a download of the last version.
SkiFree	This is a third-person game where you guide a skier down an infinite slope while avoiding obstacles, other skiers, and “snow monsters”.	This game was originally in one of the MS Entertainment packs but the author recently re-compiled it for 32-bit systems. Oddly entertaining despite its lack of sound.
Liquid War	An extremely unusual game - best described as the contents of two or more lava lamps fighting to the death. Internet play is also available on several hosts.	The 1 player mode is pretty challenging, but multiplayer mode is bound to be more fun.  Could be considered the graphic equivalent of the classic "Core War" game.
Snipes	One of the earliest network-ready games - originaly used to test NetWare. It involves text-based characters shooting other bits of text around an ASCII line-character maze.	Amazingly fun for a 30 year old game. Multiplayer mode is enabled by each player running the executable from the same shared network drive.  Also check out the other text-mode games this site hosts as well.