Labor Day weekend is a transition period for the island. The first Monday in September marks the end of summer—droves will have left the island by then. It’s also the start of school, the beginning of fall. Shopping at the Stop and Shop will tell you it’s Autumn for sure (the Halloween candy is already out). But don’t rush to put on boots and drink pumpkin spice lattes just yet or you’ll miss one of the best “seasons” on-island.