Joining songs on Windows Media Player is commonly referred to as crossfading. Crossfading gives you the ability to blend songs. The concept of blending songs enables two songs to play simultaneously to create a new adjoined sound. Although this feature is not preinstalled in Windows Media Player, it can be installed as an add-on component so properly formatted songs can be joined together for simultaneous playback.
Open Windows Media Player.
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Create a playlist in Windows Media Player to place the songs you want to join in a specific order.
Double-click on the first song for playback. When the song begins playing, click the "Now Playing" tab at the top of the screen.
Click the downbar below the "Now Playing" tab when the Windows Media Player screen redirects. Select the "Enhancements" tab and click "Crossfading and Auto Volume Leveling."
Adjust the crossfader at the bottom of the "Now Playing" window by moving the lever from left to right. Moving the lever toward the left lowers the volume of the song playing to make the next song in the playlist louder for equalizing the blend. Moving the lever to the right does just the opposite.