Fall. I do all Welcome to Chicagoland's closest orchard--Heinz Orchard in Green Oaks, IL (next to Libertyville)! Mid to Late July. Berry picking on Long Island is a popular activity during the summer’s warmest month, July. When in season, these are the berries that practically demand shortcake treatment, or at the very least a bowl of just-whipped cream. When to Pick Berries: Berries are generally in season from spring through summer, and some go into fall, but every state will have a slightly different berry season, so check your particular area on this Harvest Calendar ~ it will tell you when each berry will be ripe and ready to pick in your state. Seasonal fruits are also great for adding a dash of color to your vegetables and salads. Joy Business Academy does more than just provide job opportunities.