I've been working toward that goal for a few years and am slowly, gradually seeing more color every month and fewer weeks of just foliage. This year I added a new chapter to the garden notes I keep--I'm tracking what's in bloom on a week-by-week basis so I can look back and see where I've got gaps. I'm actually doing better than I thought! I started tracking the things in bloom the last week of May so I won't have a full year picture until next spring.

One thing over which we have no control is the weather and I expect things bloom at slightly different times every year if there's an early warm spell or a late cold/rainy spell.

Last year I added toad lily in my shade bed and it bloomed right up into October, right beside the black snakeroot. It was great having something in bloom that late in the season.

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I did that by buying whatever was blooming every month in the nurseries. It has worked pretty well over the years.

I've been gradually working on this, and in some ways, it is easier as the garden gets bigger. So, even if one section doesn't have anything in bloom, another section does. One thing I haven't managed to keep up with is cutting things back as they are done blooming, to keep it looking too shaggy and forlorn. ;) But, in general, I try to group 2-3 things that bloom at the same time in the same area, and then something else that blooms later in between in that area, so each area gets a couple bloom times. Sometimes it works better than other times, of course! One thing that worked well was planting bulbs between some of my late-summer/fall blooming plants (agastache and boltonia). The tulips, alas, got munched by the deer, but the alliums (caeroleum - sp?) were perfectly visible as the agastache was still relatively small, and now that they are done, they are completely covered up.

I also try to plant things with good-looking foliage, so I don't have just a bunch of bare stems something is done blooming. Tho I do have some plants that I need to cut entirely back at some point, of course. And I'm sure Christopher Lloyd does, too - he just doesn't show those parts in his books! Every plant goes through a scraggly or awkward transition stage, pretty much.

Gardenweed,what are those pretty white flowers?? Those are gorgeous!!
TFS
Kathi

I'm on my first year with my garden, but so far my strategy has been to pick flowers with a loooonnnnnngggggg bloom time. If the flowers last only a month, forget it! Here are some of the plants that have been blooming for months on end:

Lupines -- yep, still blooming, even with my halfhearted deadheading
6 Hills Giant Nepeta
May Night Salvia
Roses
Dollar Princess Fuchsia (I'm really hoping this is hardy in my microclimate!)
Zonal Geraniums
Snapdragon

The lupines and snapdragons are going downhill now after a whole season of continuous blooming, but I've got dahlias and hydrangeas to continue the show. If you're going for a strictly herbaceous perennial border then this approach might not work so well, but I'm sure you can still find plants that will bloom a long time and still have something closer to an actual cottage garden. I think next year I might skip the geraniums (I got them this year because I just wanted some color, fast!) but the snapdragons have been such workhorses that I plan to winter sow lots of them for next year.

I suppose I could care more about what the garden will look like come winter, but really? At my latitude in winter it's still dark when I leave for work and dark again by the time I come home, and I don't really care to be outside on weekends either when the skies are almost permanently covered with low dark clouds. I'd rather have masses of blooms all spring and summer.

The plant in the pic with the toad lily is black snakeroot, otherwise known as cimicifuga, aka bugbane. It's a wonderful plant for the shade. I want to post on this topic -- just don't have the time right now.

Merilia, the Six Hills Giant Nepeta is one of my all time favorite perennials through the years. I have found that I can cut it back when it gets to tatty looking and it will bloom again in the fall (though much shorter plant).
Self seeding annuals are great for filling in gaps both in time and spacially in the garden. I adore the asters, black eyed susans, helenium and other plants that work so hard for us in the fall. I have also found that being real slow about cleaning up the fall garden leads to some interesting garden views, especially if you plant some roses (for hips) or other structural plants. Autumn Joy sedum I never cut back, love the way it mounds up with snow in the winter. The same with the coneflowers/B E susans and the like. I have always found the fall interest in the garden to be the most challenging all the way around. This year it is going to be particularily hard because many of my old standby's do not do well in Alaska. It is quite confusing to me having "spring bloomers" blooming in July. It looks like the main garden season here is pretty much July and August when it is a veritable explosion of blooming growth. Lot's of challenges and exciting experiments ahead for me!