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Skye will not appear regularly in the valley until after you view the Black heart event, which requires you to talk to Lumina at least once (as all events require you to introduce yourself to the participants). A few days later he will start to appear. Sunday

10:00 pm - Appears on the path leading to Mineral Town
11:00 pm - At the bridge between the main area and Vesta's farm
12:15 am - Circles around the fountain in front of Lumina's mansion
1:40 am - Walking down the path between Daryl and the twins' house
3:00 am - Walking up the path from the turtle pond area to the main area
3:20 am - At the bridge between the main area and Vesta's farm
4:30 am - At Carter and Flora's tent
5:30 am - Leaves the valley
All other sunny days

10:00 pm - Appears on the path leading to Mineral Town
11:00 pm - At the bridge between the main area and Vesta's farm
12:20 pm - Goddess Pond
Remains at the pond until you wake up at 6:00 am