The Shaw Festival season runs April through October, which is also the main tourist season. Summer weekends can be very busy — Queen Street fills with visitors and parking on the main streets becomes difficult. May and September are the best months: the festival is in full swing, the wine country is at its most appealing, and the crowds are lighter.
Winter is quiet and many of the smaller shops close, but the town itself is pleasant and the wineries remain open. Ice wine harvest typically happens in January when temperatures drop far enough to freeze the grapes on the vine.