Wow, Tori, you sure have captured the home of this route perfectly. The CHW originally - and first named the Chesapeake
and Western Rail
road - had intentions of going from somewhere on the Ohio River valley to Gloucester Point, VA (on the Chesapeake Bay)! That was ever only on paper... but some of that paper included surveys into WV and on the VA piedmont. The CHW did a political dance/battle with the B&O, and the desire to get rail service into the valley at prices lower than the B&O wanted to charge was one of the reasons it was ultimately built. The B&O had grand plans to get a line to Salem (next to what's now Roanoke). There is still a B&O stone viaduct just to the west of I-81 someplace south of Staunton (yes, pronounced Stanton!

)... you can still see that beautiful stone structure, covered with trees on either side, from the interstate. As history continued, Crozet - the brilliant civil engineer after whom a little hamlet west of Charlottesville, VA is named - came over and proved that crossing the Blue Ridge at Afton Mountain was better than a gap near Elkton or elsewhere, and the C&O went on through!

As you say, that is one steep climb at Elkton. The CHW's eastern terminus is at Elkton, where it met the N&W heading North/South along the east side of the valley. The Southern railway ended up going around the mountains, through Winchester, and terminated at Harrisonburg. And, of course, the CHW meets the C&O at Staunton, just about 1/4 mile from Staunton's C&O passenger station. It was planned for the railway to also go as far south as Lexington, but that was only partially completed, and later that leg of the railroad was demolished. It was also going to head west deep into Augusta County, VA but it stopped at Stokesville, VA and today the line has been torn up back to Dayton. There even used to be a narrow gauge logging line the CHW served past Stokesville.
Yes, the CHW is very likely the owner of trackage with farm gates across the track.

It's that kind of railroad; rural and quirky. They run caboose-first for flagmen, engines in the middle of trains, and so on. The old passenger station in Harrisonburg was trying to compete with B&O, so they built it way bigger than the city needed; the CHW's history is full of those kind of oddities. There are 2-3 trains a day, but these days much of the traffic leaves north out of Harrisonburg on NS (SOU) so the lines to Elkton and Staunton don't see as much traffic. Currently, there's also another railroad company - the Buckingham Branch Railroad (
http://www.buckinghambranch.com/) - that runs trains out of Staunton to Harrisonburg... running with trackage rights from NS over the CHW (CHW is now a subsidiary of NS). There's still enough industrial traffic in Harrisonburg itself that several trains are running in the city at once, but most of the railway is indeed fairly quiet. There's still occasional interchange traffic between NS and CSX at Elkton, but less often than interchanges at Waynesboro.
Yeah, lots of overgrown rails, weird grade crossings, there's a little station out there that was an antiques shop last time I was out there (years ago), and the station at Stokesville was restored but I don't know what its occupants are doing with it now. I was thinking about going out that way on a railfan/camping trip in a couple months, lots of nice camping in the valley, very pretty place. Been too long since I was out that way.
Initially, I was going to do the route completely unsignaled, but then I found Pike's tutorials and signals, and then I went kind of nuts with signaling after figuring out I could get AI trains to share a main track when signaled. I won't say I've signaled properly, though, that's for sure.

I also want to release the route without any payware, but I got so excited about Pike's signals that I forgot they were payware!

Fortunately, I've only signalised part of the route yet, so I'm probably going to do 1) a route without any (or very few) signals and 2) a route with the US default signals. I'm betting this community will pull together honest-to-goodness proper signals for major railroads - we're already on the way I think with stuff like Pike's and SMMDigital's signal work. Also, I agree about the "protofictional" approach, since I have not lived there, just visited.
I'm truly honored to hear that my route project is enticing.

Your C&O Alleghany route is a
huge inspiration.
Red