The Crop Over festival is usually held annually from June until the first Monday in the month of August. Calypso is considered as one of the main highlights during the Crop Over season, where various Calypsonians go head-to-head to earn titles, such as the Party Monarch. A few events held during the Crop Over season are Bridgetown Market, Pic O De Crop, Pan Pun De Sand and the well-known Grand Kadooment (which is usually the last event). Many revellers tend to patronise with the popular Foreday Morning and the Grand Kadooment.

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