Perennials you can WS outside now...in a protected spot away from the critters. Rule of thumb on edibles is to count backwards(6-8 weeks) from your areas last predicted frost date for starting date for your tomatoes,peppers,eggplants,herbs and other edibles.My last predict frost date is April 15..so my 6 weeks out date would be Feb 11th and 8 weeks out would be March 25th. I love my light and heat mat set up. I sell at Farmers market so anything to get me ahead of the game is ok by me. I'll be sewing perennials ,shrub,trees and the like after Xmas in my un-heated greenhouse. Starting out under lights on the heat mat w/ perennial herbs and by 2 week of Feb.,they should be ready to move off the heat so I can start my tomatoes,peppers,eggplants and tender annual herb such as basils in the third week. I wait until 3 week of March to start my "quick" vegetables..i.e.: squash,cukes,melons,okra..etc..out in the GH. These vegs. only take 1-3 weeks to be ready to set out in the garden. Peggy

I'm just 2 miles south of the MA state line and I consider it too late once November rolls around even though the ground doesn't generally freeze for another 6-8 weeks. If the plants are dormant when you set them in the ground, it shouldn't really matter since they aren't going to start growing again until next March or April anyway. I've never planted anything after Thanksgiving but am guessing that would be an "iffy" call. My rule of thumb has always been mid-October for planting perennials altho' I've never planted anything on your list other than liatris and I planted that in spring. When in doubt, one year I did plant more than a dozen winter sown perennials in gallon pots that I set into a deep trench that I then filled in around the pots with dirt. Didn't lose a single thing that road. Just another option.

enjoy : your question begs a subjective answer. Where in zone 5 is the first variable, and the types of annuals is the second. Here in the center of the country, the weather at a particular time will be far different then , say, the east coast. Our last average frost date shows April 15th. You have to be well aware of the weather patterns in your neck of the woods. It MAY not frost after April 15th, here but it well could until about the end of April. Your annuals may coinside with the tomato planting calander only to that end. I would find out the best soil temperature for your flowers and or plant them out a couple of weeks after the last average frost date for your area. Be aware that many weather factors affect success, but planting at the correct time may only be a concern with freezing and soil conditions. Remember we are only stewerds and the planet has been doing this for a long time, plants, especially native to your area, are extremely able by design to survive the ebb and flow of the different climate and micro-climate changes, such as the natural ones we are going thru presently. Tom

Thanks for the additional photos and the bed measurements. I am fairly sure from looking at your photos that your house doesn't face due north, since in all your photos there is sun either on the front of the house (first photo, taken either early morning or late afternoon) or on the bed itself (last two photos, taken an hour or two before or after noon, based on the shadow from the house next door.) So you should probably go to Google Earth (which always has north up like a map) and find your house to figure out what direction it's really facing before we go any further on plants. It looks more like it gets close to a half day of sun and even when in shade, the shade will be bright, so you have more flexibility on what you can plant beyond shade plants. I'd still love a photo from across the street or plot plan that shows how deep the lot is and how wide, so I can figure out where to put a tree or two which are the only things large enough to ground your house and how to pull the landscape out some to also help ground the house. I would also love to be able to see both corners to see how to frame the front of the house, perhaps some flowering small trees or a taller spire of an evergreen. I still think that a more vase-shaped medium sized tree such as a Heritage birch would look great offset from the house, both over toward the right side and well out into the yard. Plant it so that the ultimate width won't overflow into the neighbor's yard. I am thinking generally that the front beds need to be made just a bit deeper and planted with two rows of shrubs and in front of that a row of perennials in just 2 or three colors with several plants per group for mass effect. One row of shrubs should be all one kind of evergreen that will stay below window height or shorter, one a long flowering shrub such as one of the reblooming Hydrangea macrophyllas such as your current Endless Summer (since it is doing well) or one of the longest blooming, and then a front row of perennials in just 2 or three colors. Depending on the evergreens and the flowering shrubs, you might have either closest to the house (though plant leave at least 2 feet with no plants behind the ultimate shrub size for maintenance and to prevent house damage.) On the walkway side, the perennials can be on the side away of the walk away from the house, continuing across the entire front in a straight line but filling in back to the shrubs on the right side of the house. This will give you something with enough mass to be visible against the house from the road (unlike the current one of this and one of that), and walking to the house will be through the garden rather than in front of the garden. Look at the first photo in thisthread from the blog of a wonderful landscape designer in the Detroit area, Deborah Silver, for something of the effect I am thinking of for your house's shrubs. She used H. paniculata Limelight, a taller hydrangea that is only just starting to bloom here, but you can choose one that will reach a height that come to just about your window sill level. The evergreens provide some color and structure for the five or so months that the Hydrangeas are bare, but don't need to be a formal sheared hedge as this yew hedge is. They can be a looser, naturally low growing evergreen. For your proportionately taller, narrower house (compared to the one in the blog), I would plant the trees off the corners, whether small flowering trees or taller narrow spires and a larger tree off to the side farther out into the yard toward the road as I mentioned above. You might even consider a medium hedge out closer to the road (though not close enough to be in conflict with winter snow plowing) to help bring higher the "ground feel" from the road (which looks like it must be lower than the house) to balance the house height. Something low maintenance with flowers such as some of the newer low care shrub roses or rugosa roses, or Hydrangea paniculata might work. For your current plants, move them to the back or side yard if you have a place for them, or advertise them as free if the taker digs them.