Does this have gapless playback?

[rurutia10]

And if so, how do you enable it? I always hear an interrupting sound when it transitions to the next song.

[phred]

This should do what you want:
Edit > Preferences > Player > Sound Effects > Remove Silence at Start and End of Each Track

[Alumni]

Yes, MusicBee can do it. Gapless is the default playback state, but keep in mind your audio files might have gaps in them already, depending on the way they were ripped or encoded.

[rurutia10]

This should do what you want:
Edit > Preferences > Player > Sound Effects > Remove Silence at Start and End of Each Track

Did seem to make a difference, but sometimes it's still there. Is there any other setting I can try?

[phred]

No other settings that I'm aware of.
Did you read Alumni's reply?