I'm playing the Union
1861 - Week 29
In the West:
Captured Cape Giradeau, My divison in ...
Mmm!, you should be able to take Winchester in the week 29, you can move 4 volunteer division to do so and one battery. I advise to create and move some militia from the north to reinforce the weakest points near Washington. You can leave only one volunteer division in Washington, maybe you can reinforce 2 spots close to Washington, and wait to reinforce Ft. Monroe until November 1861.
For Grafton I advise to move 2 cavalry units nearby, plus your 2 volunteer brigades, one skirmisher and one battery, and these forces are enough to take down Grafton, use the skirmisher first to kill the CSA battery. Afterward reinforce Grafton quickly as the main forces of CSA will head to the East area, meaning Grafton and Winchester plus Washington. I advise to build some rifle divisions a.s.a.p.
In the West Cape Girardeu should be taken rapidly and you have to reinforce this city rather quickly with a division coming from St. Louis (a built one), you can move your volunteer division from Springfield to take Ironton, etc., but I have preferred to leave it there, due to is a week point in your west defense.
I think that a better plan is to close the pass to the north to CSA reinforcing the line on the river, and then bulk in evansville and go for Nashville - Chattanooga. Same time you have to go for Lynchburg in the East to collapse the axis Chattanooga - Lynchburg in both ends and go for Knoxville.
Interesting to know next progress.