The school is located at the intersection of 19th St, Dudley Ave, St Mary's Ave, and Elberon Pl, although no one knew the name of the last street. It was just a small one or two block long glorified alley that ran along side of the Burwell Theater.
You'll note though that the intersection had 4 different street names approaching it. 19th St lined up with Elberon and St Mary's Ave became Dudley Ave. 19th St was actually a dogleg intersection in that it moved a couple hundred feet over and then ran east. There are a few other doglegs like that on Dudley Ave and St Mary's Ave.
The real mystery was why St Mary's Ave became Dudley Ave. They were the same street. No doglegs. No weird little reroutes. Just a straight street. The intersection is marked with a dot in the following image:

So, why the name change?
I looked through some old maps and finally came up with a reason I believe is correct.
St Mary's Ave and Dudley Ave were different roads. The same intersection is marked in the picture below.

Back when Parkersburg was a new town, they ran a turnpike to a town called St Mary's. The road running from it was called St Mary's Pike and is still called that in places. Where it enters town now, it turns into 36th St, but back when it was built originally, Parkersburg only reached 13th St. St Mary's Ave was where St Mary's Pike entered Parkersburg.
If you overlay the route of St Mary's Pike over the current city map, you get the following layout.

St Mary's Pike ran from 13th St to 19th St following the contours of the area. At about the 19th St intersection, it cut east for a little bit, then north. Thinking about it, about the only explanation I can come up with is that at one point, the tollbooth for the turnpike might have been located there or it had to follow property lines. In any case, when it turned north, it ran a couple hundred feet, then diagonally to what is now the intersection of 22nd and Oak, although 22nd did not exist at that time. It then ran along Oak to what we now call 26th St and ran along 26th St. At about the top of the hill, it followed the contour of the hill and ran somewhat diagonally along the hill to become what is now Broad St near 31st St and Broad St. (There is a small 1 block section of a street at the end of 27th St that was likely part of St Mary's Pike also).
It came as a fairly big surprise to me that Oak St was once the main road out of town to the north.
In any case, This is the explanation for why St Mary's Ave becomes Dudley Ave.