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Edited to answer questions in the comments.

I live in an oldish house, about 125 years old. I'm a renter so I know a lot less about the house than a buyer would but have a friendly relationship with the landlords, hence room for home improvement.

I have a terribly uneven lawn in my backyard and need to level it for safety reasons as well as aesthetic ones. It's vaguely bowl shaped, with ripples and bumps, especially near the fence line. It's also made up of many different plants, including wild violet.

My neighbor feeds local wildlife and my yard is surrounded by walnut trees, which has turned it into a small wildlife highway. I know from other questions here the rodents can burrow under the lawn, this might be part of why I have so many ripples.

I know that some plants prefer to be planted in the fall and get to overwinter (like tulips) and some plants prefer to be planted more in the season you expect to grow them in (like pansies).

I live in USDA plant hardiness zone 5A and winter is oncoming, which leaves me time to do lots of research for next year. This also means that the ground will freeze and snow will blanket the lawn for many, many, many months. We also typically see a relatively wet summer and my yard currently does not drain super well, which means that puddles form.

I don't want new grass to freeze or flood. When should I level my lawn to best balance these factors?

newtolawns
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    You say your lawn doesn't drain well. When was the last time you aerated it? If it's "never", now is a good time to do that, as the winter will cause the plugs to disintegrate. What kind of soil do you have? Do you live in a newish house? If so, your lawn is probably the "spoil" from digging the foundation, so it's a subsoil. Possibly on top of topsoil, which gives you a perched water table. Why is your lawn so uneven? Again, if newish construction, then that could be to blame. Perhaps settling of the water or sewer/septic lines? Leveling may involve adding soil, not using a roller. – Jurp Oct 25 '22 at 22:03
  • I live in an old-ish house (about 125 yrs) and I've been here 1 yr. I'm not sure about the soil and I have no idea if it's ever been aerated. Unsure about why lawn isn't level, but we do have lots of burrowing rodents (neighbor feeds them and other wild animals) and my dog running after tennis balls with his whole heart probably hasn't helped. It's a little bowl-shaped towards the middle but with lots of ripples in it, very uneven to walk across – newtolawns Oct 26 '22 at 13:56
  • The curve is deep enough that I'd assumed I'd have to add in soil, so it's reassuring to know that I'm not super out of line there. – newtolawns Oct 26 '22 at 13:57
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    Where does your sewage go? A house that old may have an elderly cesspit in the yard (even if connected to a public sewer now) and those can make a very large depression in the lawn if the wooden cover finally collapses (if they were not filled in when taken out of service - or if they are still in service!) – Ecnerwal Oct 26 '22 at 14:14
  • @Ecnerwal this is a very good and concerning question. I will have to check with the landlords! – newtolawns Oct 26 '22 at 14:19
  • @Ecnerwal We're connected to the public sewer but still trying to figure out if there used to be a cesspit. If my landlords don't know, how could I find out? Would that be something I could look up at through municipal records (when was the house connected to the sewer)? There's always digging, but hoping there's an easier way – newtolawns Oct 26 '22 at 15:00
  • Since you've clarified that you are renting, even though you are willing to do yard work, I'd not go too far off the rails looking for an old cesspit, unless you notice a distinct depression roughly 4-8 feet in diameter while working on the general lawn grading. Assume that it was properly filled when the sewer was connected, if there was one at all. – Ecnerwal Oct 26 '22 at 15:05
  • I do have a four-ish foot spot at the back of the yard that is lower than everything else and very distinctly doesn't grow grass like the rest of the yard. I'd assumed that was because water pools there and it's under the shade of the maple tree in the back yard, making it unfriendly to grass. Does that sound like what I should look for? – newtolawns Oct 26 '22 at 15:13
  • Quite possibly. You can try shoving a probe into it and see if there's a sudden lack of resistance, but really, I would not go looking, in your shoes. Fill the depression, if you like, and it will either sink further, or not. If it does, I'd class it as "really the landlord's problem to solve" since a proper fix will probably involve a small excavator and a load of gravel or stone - it would be one heck of a workout by hand, and involve considerable risk of ending up in the hole, which you definitely do NOT want to do. People die that way (from gasses as well as soil collapse.) – Ecnerwal Oct 26 '22 at 16:51
  • The property I lived on as a kid had a cistern collapse and I spent many an afterschool afternoon filling it in with my brother. Fine exercise at 17 but not as exciting in my 30's. I appreciate the clarification! – newtolawns Oct 26 '22 at 16:59

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You're a couple of months late (or 10 early) for ideal lawn planting time in your area, per most resources - later summer into early fall is the ideal planting time for new grass. However, new grass is not necessarily required, depending how you approach leveling. However, if your soil is bad and your grass is poor, you may want to bring in better materials, till the whole mess, and start over.

Link to answer about gradual leveling.

As for flooding and poor drainage, you should resolve that issue with adequate drainage - leveling (to a slightly non-level for surface drainage 1% slope that will be about as level as a lawn should be) can only do so much, if the ground underneath does not drain well.

Ecnerwal
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  • Also https://gardening.stackexchange.com/a/23988/6806 – Ecnerwal Oct 26 '22 at 01:49
  • I think I conversationally understand poor soil (low in nutrients or clay/sand instead of loam) but is there a standard for testing I should be looking at? Like, can I go to the hardware store and get a reliable, appropriate soil testing kit? – newtolawns Oct 26 '22 at 14:28
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    Normally you send a soil sample in to a laboratory (often associated with an agricultural university) for testing. "Home test kits" are marketed, in some cases, but generally considered unreliable .vs. a proper lab. – Ecnerwal Oct 26 '22 at 14:51