Too cold in winter for hanging baskets to be left out the whole time, unless you use something hyper-hardy like creeping junipers. Or if the season happens to be mild enough maybe miniature kinds of English ivy, these often hold up well.

Or hardy perennials that will survive baskets freezing up like bricks.

If you bring the planters down and protect them during Arctic fronts, then more flexibility.

Easiest thing would be to shop local independent garden centers for suitable plants, already started. Term "basket stuffers" is being used by the trade for kinds thought suitable for hanging planters.

You could try pansies, ornamental kale, primroses. They make it through winter and snowfalls for me even without shelter. Not so sure about hanging baskets, though. They would be more exposed as bboy points out, and I wouldn't want them swinging around or taking flight during one of our wild wind storms.

The nurseries will have displays and selections of good choices in September.

Lavender is a good plant for containers, but not baskets. I put mine under cover to avoid the winter wetness that can kill them. Still I lose some. They'd do better in well drained soil outside the patio in the ground.

Any flowering plant in a sunny basket will need daily water & weekly diluted fertilizer. Perhaps a nice cedar large rectangular planter with a combination of hardy perennials with seasonal accent plants would be the easy start you desire. An independent nursery will be able to help you select which will work for your situation. Bring a photo of your patio to help design what you'd like that fits that space.

If you want lots of flowers you'll need annuals. If you want easier care you might want self cleaning flowers not petunias and dahlias that need deadheading. Even easier are perennials for background color and blooms in season.

I have large wooden square planters lined with black plastic with drilled holes in the bottom. I've planted an assortment of mostly evergreen perennials in an informal design so if one doesn't make it I can add whatever I have on hand as well as an annual plant or two. A combination of some these repeated in 3 planters (2 on driveway by the front steps & another in driveway near shed) Bergenia, Sarcocca, Serbian bellflower, golden sweet flag, Purple Palace Heuchera, upright golden fuchsia Genii, Columbine, green common hosta, Carex (brown), lady's mantle, variegated vinca major and golden creeping Jenny. These pots have been planted now for 2 1/2 years, so I can lift & divide some of them if desired or just leave them to fill out more. The trailing stems are easily removed for other planters or back as groundcovers.

In some plastic window boxes I have more: one of the small varigated Carex, golden creeping Jenny, Emerald'n Gold Euonymus, variegated small leaf ivy, & spring pansies with added annual lobelia and short snapdragons. I tried spotted dead nettle in the fall, but it mildewed & died.

My easiest care 3 season large shade planters to the side of the porch steps are planted with our native lady fern and the invasive variegated bishop's weed.

Many of these plants I've received free at the Green Elephant plant swaps and have learned to propagate them myself either by division or layering. The GE is a great way to get plants that do well here without spending a dime. Save your money for planters, soil amendments, garden gloves & shoes, and tools.

will post a picture of the patio here soon once i get some light, currently midnight haha.

so hanging baskets for fall/winter not the best idea, what about some sort of row or basket trench that hangs from the railing? or is it best to use pots? and bring them inside as needed?

thank you so much for the time and replies so far, my dad was in town and I wanted to do this with him but with all the sightseeing and touristy stuff we didnt have time to work on this garden, want to surprise him next year when he comes back.

for a the time of year, would it best to start with something that is already sprouted, or to start from seed?

They do sell preplanted fall baskets. For reasons already given, they tend not to last well through the entire winter but can give you a start. Or you can always start your own.

Provided the patio railing trough is large enough, there are a number of plants you can use that would survive winter pretty much unscathed. Pansies, various groundcovers, heathers, a couple of tough, dwarf broadleaved evergreen shrubs.

Your simplest option is to plant up larger containers. Seldom will containers of any reasonable size planted with hardy plants need any sort of winter protection. I garden almost entirely in containers now and there is really no limit to what I can grow as long as it is appropriate for our zone (and a few that seem to thrive that are NOT appropriate for our zone!!). Local garden centers and nurseries often focus on fall planting and fall containers and you will typically find a wide range of suitable container plants that offer both seasonal color and winter hardiness.

FWIW, dwarf conifers are excellent container plants. Add a small grass, heather, heuchera or groundcover or two and you have an instant display :-)

I guess last winter was a mild one, I was surprised a lot of the plants in my window boxes survived all winter (unusual). I had pansies, sweet alyssum, some trailing plants with blue flowers I cannot remember the name of, mums and dusty miller. Oh and some perennial vinca. They didn't look great over the coldest part of winter but in spring, everything started growing again and all I had to do was add a few petunias!

I did cover the boxes a few times when we had some freezing nights, I figured they had made it so far I might as well see how long I could keep them going. Who knows what will happen this year.