By spline I mean laminating up to six 1/4" thick X 15/16" wide X 8' long MDF lengths. You place risers vertically so that they are anchored that way, and with their tops at the grade you want, minus the height of the spline. You place a stout nail at the centerline, driven deep enough to provide resistance and an anchoring around which you bend the MDF lengths. You glue three to each other at a time, staggering their ends by about 3", let them dry and conform to both the grade and curvatures you impose on them by using small clamps of various configurations, and then go back and clamp on another two or three lengths to get the width of roadbed you need.
If you google "spline roadbed", you'll find plenty of sites describing it.
Cookie cutter means using a scroll saw or jig saw to cut the curves into 1/2" - 3/4" plywood. With the right width and lengths joined end-to-end, probably also on risers, you achieve much the same thing.
The trick is always to have a vertical curve into and out of any grades. No kinking or abrupt changes in grade, or your engines will possibly nose out on the rising rails, or the couplers behind the engine can decouple and your train rolls back down the grade. Splines make the vertical curve automatically, and also do easements into curves. Easements on horizontal curves are very important as your curves tighten in radius.
You can derive vertical transitions into grades with cookie-cutter sections by anchoring one end with screws driven flush, and then bending it up so that it sits atop the first riser. Obviously the placement of that first riser is key. The plywood will bend and give you a nice curve, provided you use the right quality of plywood, anchor it sufficiently at the non-grade end, and place the top of the first riser so that your grade is met by that point, and no more.
As a quick observation, you show a river coming from mid-right, under which you will have two tracks? This will necessarily be a very steep water course if you want the clearances you'll need between the rail heights below and whatever carries the water. It gets worse toward the inner curve of rail.
-Crandell