Choose the "Options" tab. Tick the box next to "Part of a Gapless Album" at the bottom of the screen and click "OK."
Connect the iPod to the computer. Select the iPod when it appears in the left navigation menu of iTunes, then choose the "Summary" tab. Click the "Sync" button, wait for iTunes to tell you the sync has completed, then eject the device and enjoy your crossfade songs.
Apple's iTunes program supports gapless playback "crossfeed," which allows a song that is ending to bleed into the next one as it starts. It's possible to enable the same functionality on your iPod so long as you use a supported device -- namely, fifth-generation and later iPods, second-generation and later iPod Touch and iPod Nano devices and all iPhones. Re-sync the iPod with iTunes so that the iPod too crossfades songs into one another.
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