When is the best to plant tomatoes? Our soil is terrible.
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http://www.thevegetablegarden.info/planting-schedules
if you are planting the plants outside put them out when all danger of frost is gone. I have to start my plants from seed, and it takes about 6 weeks for the plant to be big enough to go from the grow pot to the dirt. Check with your county extension office and see if they have a master gardener on staff. They are very knowledgeable about should grow well, and what amendments to help the soil..
If you can't find a way to enrich your soil, you may consider using really big pots for tomatoes.
This depends on the area you are in. I've actually planted very early for TN using 5 gal buckets and plastic cozy coats around the plant. I purchased the cozy coats at a local nursery. They are plastic and fluted. You fill the fluted part with water. We had early tomatoes and used good soil in the container.
We have clay under our top soil so nothing grows. We grow out to orators and pretty much everything else in containers.
First amend your soil, this should be done every year prior to planting. Always plant after the last frost, if those dates are in question you can check the farmers' almanac for details.
You can plant them in pots . Put stones (golf ballsize) at the bottom and however far up you want. Put in soil, and take it from there.