Have you taken a look at William Baffin. That rose grows like crazy - it can definitely become big but I dont think you will find any rose to cover the length of that chimney.

I've been looking up some info on New Dawns as I am considering getting one as well. They look like they can get HUGE.
http://www.southampton-rose-society.org/images/2007/gtfr/dsc_0273.jpg

I think it could eventually make it up your chimney, but I'm not so sure about it being able to vertically grow as there doesn't seem much to support the rose vertically. I would assume if it was that large it would just flop over as it has nothing to really grow up. I really don't know of any real ways you could peg it up as it grows to a chimney and you could always build a trellis outlining the chimney structure, but I'm assuming you want to keep the clean look of the chimney with just the rose with it. That's a toughy.

It could climb the chimney in probably two years. He is probably planning to drill the masonry joints and plug them for screw eyes supporting wires. His concern is how to get the canes to produce bloom except where they spill over the top and crawl over the roof. You would try to bend the canes is S-shapes so some of it is at 35-45 degree angles. I'm not sure it could be done with ND. Does he need a rambler, maybe Super Dorothy?

This is such a beatiful stone chimney. I would not cover it totally. I would plant the rose bush at the corner of the chimney/side of the chimney and train to go up then sideways when it gets between the 1st and 2nd floors, towards the edge of the roof. This way, you can also reach with a ladder if it needs to be pruned. All these experienced rose gardeners can suggest some roses, but it should have flexible canes and of course it should please you.

No advise, but HAD to agree with senko: Do NOT cover that gorgeous chimney!

I have to agree with senko's idea. That sounds pretty good now if I put my artistic imagination into visualizing it.

If you bought 2 New Dawns(HUGE!) and let them grow up the side and grow somewhat up the angle on the chimney before the 2nd floor, you could still see your chimney and have the New Dawn's quite large and possibly still able to lay on that angle somewhat. Also as a plus, you could let the New Dawns grow out somewhat and slightly fill the side of your 4 windows so that you see them peek in as you peer outside. I would think it would take some consistent pruning to keep those beasts in shapely form, but senko's idea sounds great.

You have a lovely home. JMHO, but I wouldn't want to cover the whole chimney either. New Dawn is so still and thorny, it'll beat you to death trying to prune it, trust me. I'd rather rig up some sort of "wire espalier" as previously mentioned and put a climbing pinkie or something on it; few thorns, very flexible, lots of blooms. For a fuller bloom than that, perhaps a Noisette (ie, La Biche) would be suitable.

meant to say New Dawn is very STIFF.. (not still) I'm going to bed now... LOL

You have a beautiful home! What a gorgeous chimney.

I'd be concerned about the wood exterior being covered by vegetation (ND will be spilling way beyond the chimney)--will it enable moisture damage, encourage rot, insect infestations? It's also a way for rodents climb up to your roof and into your attic (that's a problem here, may not be a problem in your area). You want to be very careful about what you allow to grow on your house. Damage can be very very expensive to repair on a house. A rose on a pergola--a pergola isn't your house, you know?

I agree with Hoovb here - about the possible damage to your house, since your house is made of wood.

I used to have a climber - a jasminoides solanum growing beside the wall of our old house. Three years later, there were cracks appearing in the inside of the house, and I had to get rid of it quickly.

Perhaps you could build an arbor leading to the chimmey or maybe framing the chimmey instead?