My advice? Don't do it. You will soon get tired of cleaning up the dropped fruit. Steve in Baltimore County.

I'm going to plant it in the woods were we don't usually walk, outside the fence. It'd be great for deer and such.

In that case may I suggest a semi-dwarf Winesap from Miller Nurseries in New York State. However there is a fellow in Virginia who has developed some seedlings particularly adapted to this area. They are relatively disease free and quite drought tolerant. My son planted a couple on our place 10 yrs ago. They only attain a height of 12 ft or so. If you are interested could possibly find out who and where, Steve in Baltimore County.

I'd try the fruit/orchard forum here. I have a lot of apples espaliered as a screening fence, but have not heard of a 'wild' apple. Most don't like much shade either. There are some varieties that have evolved to need less spraying if you wanted to pick some too (e.g. Liberty, Williams Pride, Pristine, etc), but fallen fruit tend to also draw undesireables. I don't know that winesap is the best for this area. You need to be prepared for the whole lot of wasps, hornets, skunks, racoons, oppossum, etc.

If it is just for wildlife, you may be better off planting a serviceberry. They are a small tree or multiple stem shrub that also have showy flowers and fruit. They can get by with a little more shade, the fruit is good for wildlife, but not large enough that dropped fruit turns into a pest issue. Blueberries also take some shade and produce fruit for wildlife.

I grew up in western New York, in an area that has since been extensively developed but was farmland in the 30's, 40's and 50's. There were "wild" apples in what was probably an abandoned orchard near my house and many of the apples were quite good, although it varied from year to year. The "wild" apples you see are probably either similarly from abandoned orchards, or are seedlings that have grown up from ordinary cultivated apples from such orchards or tossed by people so they are probably the same species as the common domestic apple. The only other wild apples you would see up there are various Crataegus species, most of which have very small fruits.