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How to Plant Tomatoes in the Winter. Part of the series: Tomato Gardening Tips. Tomatoes may need extra protection from the elements if you plant them in the winter, so prepare yourself with a plastic cover or an indoor area for potted tomato plants to stay when the temperature drops. An expert gardener gives you the details in this free video on tomato gardening tips. Read more: http://www.ehow.com/video_7502603_plant-tomatoes-winter.html