Can I replant herbs that have wintered in the garden?
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I think you'll find the info in this article helpful-http://www.offthegridnews.com/survival-gardening-2/herb-garden-maintenance-for-fall-and-winter/
I think you will find that most herbs are hardy and will survive the winter you can repot or leave them where they are and they will be ok.
Oregano yes! Cumin no but you can harvest and plant seeds. So very easy to get even small starts from many perennial herbs And other perennials he may have left behind. Think of them as a gift from him every year they come up! Enjoy!