I've only been to one mutli-day festival, and that was the Bonnarroo 2007 Music and Arts Festival.
Line up highlights:
Tool
The Roots
Clutch
Ween
Rodrigo y Gabriela
The White Stripes
The Police
Tortoise
Gogol Bordello
Stanton Moore Trio
Flight of the Conchords
Demitri Martin
Dave Attell
Lewis Black
and enough drugs to kill all of mainland Europe and the Shetland Islands.
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