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Since you mentioned pots, have you thought about planting something in nice decorative planters there. That way if whatever you are growing isn't doing well, you can just move it to another spot.
Are you trying to see the plants from where you took the picture? It seems you need something with mass in order to see the plants from the road area.
Delphiniums register "cottage garden" in my mind. Lots of staking, pretty sensitive, labor intensive. Fine for flat, level gardens, but not sure how much of that you would want to do on a hill...
If you like the delphinium look, though, how about anemone japonica? They will handle dappled shade with a moist, loamy soil.
Anemonies would be a great choice, however they are invasive. I had some at my old house and I could not keep them under control. If they are in an area where this isn't a concern, they're good.
If you decide to go with daylilies, I can recommend smokeysdaylilygardens.com. They separate the categories into repeat bloomers, colors, and height, so you could be assured of getting the height you want. My repeat bloomers bloom all summer with just a bit of dry fertilizer a few times a year.
I have one which is 6 feet tall and another about 2.5 to 3 feet. I'm sure there are other varieties in between. What about Queen Anne's Lace? I love it.
Canna Lilies get huge depending on the variety and I've grown them in sun and shade.
Miscanthus and other ornamental grasses are a must for a tall border
Hollyhocks?
somebody mentioned liatris. Unless there is a variety I'm not familiar with I would never consider it "tall".
Look what I found? All I did was google Tall perennials for zone 7b and this came up.
With the shade and height requirement, I'd look into rhododendrons. They are spectacular, though for only a short period.
Big old fashioned roses, such as Hybrid Perpetuals, would be great, except it looks to me like you have too much shade. If my perception is wrong, then I'd go with pillar, grandiflora or hybrid perpetual roses.
Ooh I like the pictures. Now I've seen it...it looks like there is a tree there, too? I'd second noKudzu's suggestion of rose of Sharon. These self sow like mad, so I'd get a sterile cultivar.
In my yard they flower in shade and grow right up to the trunk of a norway maple. I actually hate them, but they'd live in the area and may look ok. They leaf out late and have pale yellow fall color. But hummers like the flowers. I'm not sure if a sterile one will be good for hummers, though.
I'm reading a great book called "Designing Gardens with Flora of the American East" by Carolyn Summers. Has someone recommended native azaleas? These like full to partial sun and have sweet smelling flowers in Spring. They're mostly deciduous. Some also have nice fall color.
If it is moist back there, you can try ostrich fern. I've read these can be invasive, but mine are in zone 7 and are anything but. I've also seen some in other gardens...and they behave themselves. There is a cultivar called the King that can get over 6ft tall. But like the Rose of Sharon, these wake up a tiny bit late, and don't seem very interesting in Fall. Not that I can remember, anyway.
I have Rose of Sharon's in my backyard on the wooded hillside. And they're more like medium height columnar shrubs.
I'm looking more for very small shrub or flowering plants. I know the rosemary was a shrub but it didn't get crazy big like a rhododendron can get ....or as big a-round as a hydrangea. It was the perfect medium -- taller than wide -- size.
Since tall asiatic lilies are an option -- in terms of a growth habit...would you say they can sprout up and spread to other areas where the weren't planted?
For example the rosemary just gets bigger and grows larger 'in place'...it might eventually grow wider -- but it doesn't spring up a foot over from where it was...and I won't have more plants of it than I started with. (which i not what I'm after)
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They leaf out late and have pale yellow fall color. But hummers like the flowers. I'm not sure if a sterile one will be good for hummers, though.
