I have been thoroughly charmed by the Chestnut Rose trimmed up into a tree at Louis the Plant Geek: http://www.louistheplantgeek.c...

Grafted standard roses don't speak to me at all, but this rose would make a lovely small tree next to a playhouse. Are there any reblooming roses with similarly thick, trunk-like canes? Thanks!

There is a reblooming Chestnut Rose but it is very thorny so it might not be a first choice next to anything like a playhouse.

Does ARE's rebloom. That's what I ordered for spring. If not, where could I find one? I've seen a very old specimen and it was awesome! : )

If it is the double one, I believe it will.

Thank you, Pork Pal!

If it is the double form of R. roxburghii -- "Chestnut Rose" -- it will probably repeat -- but NOT the sort of heavy repeat bloom you would get from a China, or Tea, or a modern rose. It's an "occasional repeat."

HOWEVER -- take heed of Porkpal's mention of prickles. Chestnut Rose is a THORNY DEVIL.
See:
http://www.helpmefind.com/rose...

For a rose that would climb a tree and repeat bountifully -- in a mild enough climate -- you might look at 'Mutabilis'.

Though it is not "billed" as a climber, I have seen 'Mutabilis' aggressively climbing an oak tree.

Oh yes! It's an absolute beast..... more like a huge shrub, but really amazing hips. What about one of the old ramblers?

Wowza!!!! That is amazing!!!

Both Mutabilis and Louis Phillipe are nearly thornless, will climb a structure with support and would be good next to a playhouse. My Louis Phillipe grew over 20 foot tall into a pear tree. Both roses would need support though.

Thanks for the input everyone! I've found a couple of candidates for a rose tree.

Mrs. BR Cant
https://www.rosesalesonline.co...

And "Miss Atwood" found rose.
Here's a 6-year-old MONSTER of a shrub, 11'H x 16'W:
http://www.helpmefind.com/rose...

And here's a single-trunked specimen:
http://www.helpmefind.com/rose...

Other roses that grow to enormous free-standing shrubs in my zone, and may lend themselves to trimming up, include Monsier Tillier and Prosperity.