My preference would be to plant a clematis, but I am biased by the fact that I truly love clematis. Look at Betty Corning which would nicely cover the bench and should be hard pruned in winter so the bench is visible. It has lovely lavender bells and is a large vigorous clematis. If you want a small clematis that will leave more of the bench exposed, look at Arabella which doesn't climb but you could guide onto the bench. It's also a hard prune clematis like Jackmanii, and either would look great with Jackmanii.

You could use 2 different vines to add depth and dimension --- One flowering and one not, or one green and one variegated. Are you looking for a winter-hardy perennial? If so, what Zone and I'll try to find some interesting suggestions. You could turn that tired old bench into a focal point with the right plant. And any preference for color?

Thank you for the responses. I ended up choosing clematis "Snow Queen" for the site, mostly because I was at the local garden center for other reasons and spotted a nice one. I looked high and low for Boston ivy around here, but alas, I couldn't find any. I'm technically in Zone 6a, but we've had a couple of 5b winters the last few years, so I try to make sure all my perennials are at least winter hardy to 5.

Well, if you stumble across a Boston Ivy in the future, I think it would add a nice contrast to your Snow Queen. Would look cool with them planted at opposite ends and would blend in the middle. =)

That's my exact idea! Actually, I planted the clematis in a large galvanized bucket I found (which I then weathered with acidic toilet bowl cleaner, and then drilled a bunch of large holes in the bottom). It was a good thing, too, because the original spot I intended on planting it was just a bit too shady for a young plant without long vines yet. So I moved the planter to a sunnier spot on the other side of the bench, and I have the vines trailing along the rock border of me bed for now, close to the bench but not quite long enough yet. If I find some Boston ivy I'll plant it on the other side. Am I correct in assuming that Boston ivy will tolerate a bit more shade?

While I'm on the topic, how should I protect the clematis over winter, since it is in a metal planter that is only about 15" in diameter? That's not a whole lot of soil to offer protection from freeze/thaw cycles. I'm thinking of mulching the top and then wrapping the bucket in some foam or an old towel and then plastic to keep out the snow and rain. If it wasn't a vine or if it was a Type 3 clematis I'd just prune it and bring the whole thing into the shed. But if the vines start climbing up the bench as planned, that's not really an option.

I don't know if you can keep a clematis in a bucket that size for any length of time. They have quite large root systems, and I've only seen them in containers more the size of a whiskey half-barrel.

Thanks NHBabs. I wondered about that. A half-barrel pot would be too large for the space. Hmmm. I might have to transplant it in the ground along the back fence and come up with another use/plant for the bucket.

The other option would be to cut out the middle of the bottom and use the bucket as sort of a "raised planter" ... The roots could extend beyond the bucket into the ground itself but keep the look you were going for. As for winter protection in that case, my mom protects her roses in Zone 5a Nebraska by putting a tomato cage over them and filling with leaves/mulch. I'm thinking the same should work for you. I'm thinking foam or an old towel would retain too much moisture and you definitely don't want to cover in plastic ... maybe burlap, if anything.
As for Boston Ivy, it prefers full sun but will tolerate partial shade ... Full sun allows them to achieve maximal fall color.

I like realcoke's idea if you decide not to plant it in the ground. A hefty pile of mulch around the bucket might work as well if there isn't anything planted close enough to be hurt by it.

Thanks everyone. I decided it was probably best if I plant the Snow Queen clematis along the back fence, where it can mingle with the Jackmanii I have there already. It should be a lot happier there. I used the galvanized bucket for some corydalis lutea, which does really well towards the front end of my border. I found a large wooden bucket that I'm using as a planter on the side of the bench for now, until I can find a nice vine that will do well in the shade.

The problem with ivy is they tend to be invasive. My neighbor has ivy and it has completely ruined my cedar fence. I have to break my back every spring trying to pull out the encroaching ivy.

Danielle, whether ivy is an issue is dependent on where you are and how cold it gets. It is a major issue in the Pacific northwest and probably some of the other warmer areas of the country, but shouldn't be an issue in the poster's location in zone 5b/6, I don't think. Here in northern zone 5 I can't grow it except as an annual.