Kingston works best when you keep your expectations local and walkable. The city rewards slow movement: coffee
a lakefront detour
an independent shop
then an evening set without needing a full itinerary.
The downtown core is strong because everything stacks. Music
food
history
and water are all close enough that the day can shift with the weather.
If you only schedule one anchor experience
make it something after dark. Kingston's smaller venues give the city a scale that larger festival markets often lose.