You need to look at the days-to-harvest numbers on the particular variety and plan your garden accordingly. As a general guide, okra takes 50-55 days from seeding to first harvest, pickling cucumbers take 50-60 days, slicing cucumbers take 60-65 days, summer squash takes 45-55 days and winter squash 80-100 days. You can count back from the day you want harvest to begin and get your approximate date of planting.
One additional note is that okra and winter squash does fine in the summer. Cucumbers and summer squash may not set and develop its fruit well in the blazing heat of a southern summer.
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