My 2 cents...don't do a brick ring. They are so old school and look cheesy. Also when your talking a solitary tree your better off creating a smaller mulch ring so you don't draw attention to the circle but the tree. Multi-stem or low branching trees you can go with a larger diameter ring. I'd take a shovel dig about 2" down to create an edge about 3'-4' in diameter...you could even cut 3" inside that ring you cut and remove that grass and flip it upside down on top of the grass to the inside...that will create a nice little trench for the mulch to grass transition. The grass you put upside down then gives it a little more depth. Don't use round-up just cut it real short and/or use newspaper to put over the grass then put the mulch over it. Not a ring...but an example of the look you can acheive. I just did this one 3 weeks ago.

I suggested wood chips to hubby but that's a no go also :( He wants to kick a soccer ball around w/ the kids. @owlnsr when you say you grow "turf" in shade, do you mean grass in a traditional sense? Last summer we had a major drought (like no rain for all of July & August - not normal for Boston) so it was a dustbowl, but we've only owned the house a year and the real estate photos showed a green lawn in years past that upon further inspection was weeds. We did have some weeds last summer and also ferns popping up in the areas that are always in shade. I just get worried when I see so much online about "you can't grow grass unless you have 4 hrs of sun" - don't want to waste money/time on a doomed enterprise. I've been researching ground covers and am looking into Corsican mint. Even if we get grass to grow, I fear that mowing/watering will never be our strong suit...

Can you add some additional photos from within the yard? Its hard to judge how significant a slope you are dealing with and we can't really see the retaining wall. Some photos facing the house would also be helpful.

@JoJo (Nevada 9A) I like the woodland garden idea, but not sure what that could look like. Do you have a picture you can share? Great point about the trees taking much of the soil. I know very little about gardening or plants (learning as I go – more of my husband’s territory), but the soil does feel very different here. Almost clay like. The soil is definitely full of roots -there’s tons that are poking up through the soil. Is that a sign the bedrock is right under the surface and we need to be careful with what we plant? @callirhoe123 When we first moved in we had a ton of vines on the fence and we didn’t love the look, especially since there’s so much fence line to cover. @Christopher CNC A gate in that section of the fence does sound good – especially when my daughter tossed a frisbee over the fence and it was a long walk to go get it. Love the idea of painting it black. Starting to think everyone is right- it probably just needs a good clean up and it will make a huge difference. Especially since we’re not replacing the fence. @ken_adrian Adrian MI cold Z5 I love your questions – and yes I am being generous calling it a retaining wall! Some more pictures of the property below. We have almost an acre, but the property is very wide, not deep. There is an inground pool on the right side of the house on the hill – that’s the additional fencing you see. It’s abandoned and needs fixing, but that’s hopefully in the budget for next year or following. For the portion with the retaining wall (actual wall, not just rocks scattered about 😉 ) we are thinking of potentially building a fire pit area in that space? That’s just an early thought though and we haven’t spent time investigating. Maybe at the base of the stairs we’ll level out the yard a bit and put pavers down to build a patio area? Feel free to tear apart these ideas and impart some wisdom!