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Tomatoes... our picky plants! Never water from the top. You know those big recyclable 4 gallon milk containers? As you plant each tomato plant, dig a deep hole beside it. Punch small holes in the milk container after it is filled with water. A wee bit of liquid fertilizer early in the season is a great addition. Remove lid to water plants, fill when needed and cap again, No overhead watering!
It will soon be time to plant tomato plants. This is a great way to make sure they get water all summer long.
After your soil has been prepared to planting, and you have your tomato plant or plants ready to put into the soil, do this. Take a 1 gallon plastic milk or juice jug, poke or cut a small hole near one corner (be sure to save the cap). Plant your tomato plant and bury the jug (with the hole toward the plant), up to the neck next to the plant.
Some gardeners have good luck using buried PVC pipe with holes drilled in it to water their tomatoes. This is a page about watering tomatoes underground with PVC pipe.