As an example, look at the player piano:  This existed in a couple of versions:  One was very much like a music box, and it played with very little expression.  A more sophisticated one make recordings that captured the style of the person making the recording (pianist)

https://en.wikipedia.org/wiki/Player_piano

The principle is pneumatic -- air powered -- for all but the last generation.  Lots of instruments can be automated, but many are difficult to do at a volume suitable for a outdoor workforce.  All of them require a person pumping bellows, changing paper rolls,etc.  

One of the most versatile entertainments for this situation is the work song.  I have done many canoe trips as troubadour singing songs of work, war, love, and life.  I had about 8 hours of repertoire.