You just take off as much as you need. You can air dry it, too. It's better not to remove too much of the plant. Herbs are very easy to grow. My oregano overwinters and blooms in the spring. But, I live in a very warm climate, and I have it growing along the side of my house.
I have to cut my oregano back several times throughout the summer. Otherwise, it will take over my garden completely!
I planted 1 small plant probably 8 years ago. It never dies completely in the winter and just gets bigger every year.
No way I could ever use that much, but it's pretty to look at and great to smell.
I live in a warm climate and my oregano survives the winters here. It gets to 30 deg. F most winters. I cut half of it, wash it in plain water and dry it by hanging or laying on a towel and letting the air dry it (takes longer than hanging). After it's dried, I put in a container and freeze for at least a week. This is yucky, but it kills insect eggs that may have survived the washing. If you don't do this, you'll probably get critters in your jar. I share with friends who cook. It also makes a really good antibacterial salve. Good luck!
I only grow lavender and just started lemon balm. But I've picked up a couple of mesh produce bags from my local grocery store. I also found them at a farm stand (on a local farm). They're supposed to be for fruit and veggies and look like they can be used to rinse the produce when you get home. But I've used them to dry some herbs I've picked up. The mesh is pretty fine but still allows for air circulation.
Oregano is in the weed family. You practically need napalm to kill it. Be prepared for it to spread aggressively unless you really rein it in. I would cut it back by 1/3 to 1/2 when it gets to be about 8-12" tall, then give it regular trimmings after that. I love the flowers, and so do the bees and other pollinators. Oregano is such a useful and wonderful plant.
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