Everybody has a story to tell of how their grandma would stick a piece of rose stem into the ground and then place a Mason Jar over the stem to make it grow. There are tales of how the early American settlers of the 1800's traveled to the far reaches of the wild west in covered wagons, with grandma bringing along "starts" of her favorite roses from back home. Perhaps the treasures of these "monsters on wooden wheels" were raided, and they discovered the Yellow Rose of Texas hiding under the bonnets of the women. Or maybe the settlers used their precious "starts" to barter for provisions along the endless dusty trails.
You may even wish to cut your cuttings down to 3" to 4" and double your plants, but they will be more prone to rot or dry up faster if you let the soil dry too long. The cuttings that are 6" to 8" seem to do much better, and if cuttings are even longer, the water has a longer length to travel up and down, and the cutting may end up more dehyrated with the upper part dying off. So 6" to 8" is a happy medium.
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.
Allow rose hips to develop by leaving dead flowers on the plant. The flowers are typically pollinated by insects, or pollinate themselves in some varieties, so there is no need to pollinate by hand unless you are breeding specific plants together. Leave the flowers on the rose plant without cutting them. After they wither, small fruits known as rose hips will develop in their place.
Take a sterile Q-Tip or small sable artist's brush, and dip it into the rose pollen you want to use. Then dab the pollen-coated Q-Tip or brush onto the stigma of the rose you have selected as the seed (female) parent. You could also simply use your finger to apply the pollen to the rose. Repeat this procedure after four hours, and then again after another four hours. Label the rose hip with the name of the seed parent as well as the pollen parent, i.e. Fairhope x Miss Flippins. The name that appears first is always the seed parent (the mother), and the second name is the pollen parent (the father).
Protect the roses over the winter. Roses that are left tall may be damaged by heavy winds and frosts during the winter. Trim the canes down to 2 feet (0.6 m). Tie them together with twine, to help protect them from inclement weather. Heap a mound of compost around the base of the bush, then top it with a layer of straw. When the weather warms to above 51 degrees, remove the compost mound.
Cover the cutting loosely, pot and all, with a plastic bag or plastic wrap and keep the soil moist. Putting a tall stake into the pot will hold the plastic away from the leaves. If the plastic touches the leaves, they remain wet and can succumb to a fungus disease. Along the same lines, make sure the condensation can escape from the plastic or the stem will rot.