Answer: Pruning for this particular rose is done in the early summer right AFTER it blooms. The reason to wait until summer is that it blooms on old wood. I would not prune it now as we go into winter as this could result in excess cold damage in addition to removing your flowering stems for next spring.
As with other old fashioned once blooming roses -- and unlike the hybrid tea roses -- you would never prune this one off short. A severe pruning could severely shock the plant and possibly kill it. The rule of thumb with these is to prune no more than a third of the plant. First remove any dead or damaged stems, then reduce the overall size by removing the top third of each cane or stem. Then remove anything with a diameter smaller than a pencil. This once a year pruning should help restore some vigor to the plant. In addition, you could consider treating it with some TLC as a healthier plant will generally grow and bloom better.
I am concerned that your rose has only two main canes, usually this type of rose would have many stems coming up from the ground. (This is an old fashioned rose that can grow very large, in the 10 foot tall and wide range or even bigger usually with a thicket of canes in the center.)
To stimulate vigorous new growth, take care to water the plant deeply during dry spells. I would also suggest you top dress with a good quality compost in spring and fall, and use a general purpose or slow release fertilizer next spring and summer per the label directions. Also use an organic mulch year round, maintaining it in a flat layer about three inches thick. This should help feed the soil slowly as it breaks down over time.
Finally, to try to stimulate new cane growth from the base of the plant, you might sprinkle about a half a cup of Epsom salts (magnesium sulfate) on the soil around the plant once a month or every six weeks from spring through fall.
In a few years, if your plant develops lots of new canes from the base, youmight consider removing one of the very old stems, and then eventually the other original stem. Once it is growing vigorously and gets dense, I would suggest removing a few of the oldest canes each year by cutting them off as low as possible at ground level. But for now since it only has two, I would err on the conservative side and leave them both intact except for trimming the tips. Hopefully a regular pruning and care routine will stimulate new growth from the base of the plant and eventually you will be able to thin out the oldest canes a few at a time. But for now, leave them.
Good luck with your rose!
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