Piilu is a great one

I would suggest a viticella.
Or, Duchess of Albany will cover your obelisk quickly and flower for a very long time.
She does for me.

I considered Piilu but thought it might be too short. I think I'm going to put 2 piilus in pots to see if they will over winter. Duchess of Albany is really pretty! Do you have one & if so can you send a picture? Thanks

Piilu reaches the top of my 5' obelisk and folds back down over herself to the ground. Hard pruned every year.

Not sure I want to have pink because I have a pink John Davis rose next to this spot.

I have Ramona and Viola on 7' obelisks. They both fill them up nicely. I'd say that Viola is taller, more massive and more prolific.

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Viola
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Those are very pretty thanks for posting! I have a Romona It was pretty this year too. The Viloa is a nice color I might have to get one of those if I can find it.

I second Viola. I also have one growing on a pillar--it is gorgeous and long-blooming.

Kate