I have successfully taken rose cuttings with both new and old wood. It is important to let the new stems sufficiently mature. The new wood is usually mature enough after the stem has just finished blooming. If you don't let the stem mature enough, then it usually becomes limp and will die before you can get it to root. I take cuttings from new rose stems in the spring right after the first bloom cycle. Then in early to late fall (in Southern California) I prefer to use more mature or old wood. When using old wood in the fall, I will remove the rose cuttings from the Mason jar, baggie, or mister, after only several weeks since it is cool enough then for them to root on their own as long as I water them daily.

When the rose hips are ripe, after about four months, cut them off the bush. Some rose hips will turn yellow, orange, or red, but others stay green even when they are ripe. You can open the hips as soon as harvested or you can store the unopened hips in the refrigerator for several weeks before opening. Then slice the rose hips in half, and open them with a knife. A butter knife will do just fine. Now, dig the rose seeds out of the rose hip with the knife, and throw away the pulp and outer shell.   
Selecting a disease-resistant rose is the single most effective way to avoid problems and the need for chemicals. You might start by considering some of the old rose varieties, many of which have natural disease resistance. You can also look to many of the modern roses, which are now being bred for improved disease resistance. Hybrid teas are notoriously disease-prone, and seem to lure every insect pest from miles around. They can be difficult to grow without an arsenal of chemical dusts and sprays.
While your cuttings take root, keep them covered and moist. In a garden bed, a simple DIY mini greenhouse does the trick. Just place a bell jar, a garden cloche or an overturned mason jar over the cutting. A clear plastic bottle with the bottom cut out and the cap removed works, too. Water the soil regularly to keep it moist, but not soggy. Your mini hothouse will keep the humidity high inside.
Select two roses that you want to cross-pollenate. The blooms should not be too tight, perhaps about one-half to 3/4 open. Carefully peel off all the petals. The rose stamens inside should look golden yellow and fresh. With sterile tweezers or cuticle scissors, carefully remove all the stamens at the base of the rose hip, so you do not damage the pollen sacs (anthers). Place the rose stamens into separate, clean film canisters, and place the canisters in a dry place, but not in direct sunlight.   
Ever wonder if you could root and grow roses from a branch of your favorite rose bush? Roses actually root rather easily. However most roses are grafted onto the rootstock of a different type of rose than the top, flowering portion, so the rose you root and grow may look nothing like the rose you started with. Grafting is done to improve strength, disease resistance, or hardiness, and even if you do get something resembling the parent rose you took your cutting from, it might not have that rose's hardiness. Rooting a rose cutting may not be hard to do, but it is something of a gamble.
I bought hybrid tea roses last year. Not long after the first blooms, we moved one because it was interfering with the sprinkler system. It looked unhappy at first, but continued to bloom throughout the season. This year, it does not have so much as one leaf, no new foliage whatsoever, however, there is still green inside the stem towards the base of the cane. Is it done for, or is there a chance it will come back in it's second rear?
Black Spot: Rose plant leaves with black spots that eventually turn yellow have black spot. This is often caused by water splashing on leaves, especially in rainy weather. Leaves may require a protective fungicide coating, which would start in the summer before leaf spots started until first frost. Thoroughly clean up debris in the fall, and prune out all diseased canes.
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