This article explains crossfading and how to enable it in Windows Media Player.
Windows 8.0 Professional – Enable Crossfading in Windows Media Player
Luckily, Windows Media Player 12 has just the feature to make this happen (for Windows Media Player 11, check out our tutorial on how to crossfade music in WMP 11 ). The audio enhancement feature in question is called Crossfading, and it can easily be set to happen automatically (if you know where to look, that is).
Once configured, you will have a new way of listening to your music library; this audio mixing technique will make the way your music collection is played sound more professional and more interesting to listen to. If you have already created your own custom playlists, these will also be processed when crossfading is set up. The caveat to using this facility, however, is that you cannot crossfade tracks on audio CDs.
If you'd rather set up this awesome audio effect instead of having to suffer through the (sometimes annoying) silences between songs, follow along with this short crossfading tutorial for Windows Media Player 12. You'll not only learn how to enable this feature (it's disabled by default), but also how to vary the time that songs overlap for that perfect crossfade.