Drainage depends so much on your local soils and site conditions. We have silty soil here with the only way to dry out an area is to install a series of parallel drains that empty to daylight. The more impervious the soil, the tighter the spacing of the drains. You could start with one drain to intercept water as you suggested and see how much it helps

Water needs someplace to go and it's often against code to drajn it to the street or your neighbors. So, the first question is where would drains drain to?

My experience is a birch will, when it gets big enough, soak up a lot of water. You probably need the right sort of birch. I planted one in a wet spot and 10 years later, the birch was huge and lovely and the lawn beneath it no longer slways wet.

Consider hiring a landscape architect to help you evaluate drainage issues and possibly plan a gravel and stone rain garden with native plants, ground covers, and small trees that thrive in wet conditions.

Dry Streams, Rain Gardens and Bog Gardens · More Info

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The yard below isn't at all right for your yard, but it does show large yards can be divided into activity zones with connecting pathways. The conencting pathways might be as simple as stepping stones.

Your yard is very parklike already. Apart from the wet areas, think about creating zones for groups to gather--shade structure; eating area; fire pit with seating, etc. Go to small parks nearby and see how they do it. Keep an eye on Craigslist or Facebook Marketplace for attractive outdoor seating you can keep outside year around. But have a plan so that the whole and the parts relate aesthetically.

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"Park-like setting" can be interpreted many ways. On one end open, natural, free-flowing. On the other defined spaces, hardscape. If you want a sort of "bandshell" area, then planting more to "soak" up water will probably encroach on that, nor can you rely on that method when you find you need a dry surface (neighborhood picnic is set the day after a rain deluge). Adding a rain garden or gravel areas takes up space too and needs engineered for the amount of water if you have surface activity that is prioritized.

So it sounds like you will be heading towards underground drainage. In the 2nd pic I see a slope down into the yard, the 3rd pic looks like the neighbor behind you is lower. Water can continue draining onto your property, and you can continue to push it to whereever else. You just can't exacerbate the natural flow. So you have to evaluate all the grade elevations, where the water is coming from, where it can go, the soil characteristics, and the existing plantings in how they work with your activities.

I find willows are water hungry beasts and fit well into park like settings I love weeping willow to sit under too.

Wow, Akhilesh! Your "Photoshopped?" renderings are phenomenal. Each one introduced an idea or format I'd never been able to imagine. First, what program did you use to superimpose these on my lawn? I especially like the one with open space at the top as I do want people to feel welcome to view what's happening below. I grew up being able to play croquet or volleyball in my yard on a farm, so being able to view inviting activities along this slope is important. I can now picture paths that welcome neighbors passing by to perch a foot on a log for a lemonade chat, or putt a golf ball on an imperfect green down the slope. To the right, just behind my house, is yet another section with a firepit and stone barbecue. As all this progresses, I intend to have a circular stream and coy pond. It's never-ending as is my love of renovating/revitalizing this, my Central New York fairytale home. Thank you so much for your inspiration. *If I know the program you used I will be in 7th heaven! I'll post my own tweaks to what you posted. ...Thought I'd also post what it looked like when I purchased it. This photo shows the first little section of ivy I removed as well as the door I painted red right after my purchase. So elegant, yet a zoo-full of birds and varmints chirped relentlessly day and night among the ivy and stucco! K

I love your home so charming. I would love to see what you end up doing.

Seabornman... Thanks! Yes, your suggestion makes perfect sense. Below some really good soil is clay, frankly. About 1/3 of the way down the yard I was thinking of either a French drain or longish water garden w/drainage going toward the edge of the driveway, then downward. I have this bigger vision of a coy pond at the bottom. ...or maybe I just need to build a water park!!! :) Does it make sense to put a French drain across the yard halfway down a slope, or does it really need to be done at the very bottom? ...Yes, probably need to get a landscape architect out! Thanks for all your input!

Thanks, Kate, I'm glad you liked the renders. I'm using https://www.dreamzar.app/ to create them.

Having seen the latest picture can I just point out that your house wasn’t engulfed by English Ivy, Hedera helix, an invasive evergreen non native. It was Boston Ivy, Parthenocissus tricuspidata, a deciduous vine with fabulous fall colour.