I would say make reservations now for CO Springs for dropping off. Last year we did a cross country move and dropped DD off in the middle. We arrived a few days before I-day so she can rest after some long driving days and gave her some more time to acclimate to the elevation.
We have always planned out out cross country trips by visiting national parks, picking a few we definitely want to see and then finding some rest stops in between. There are some wonderful state parks as well that are often less crowded than the national parks. Not sure if you camp, but this is what we did and just pitched a tent along the way. Regardless, if you are camping or not, best to figure out a plan and make reservations now. Just make sure that you can cancel them, if needed.
From CO to MD, we camped at Yellowstone, Grand Teton, stopped at Mount Rushmore and stayed at Custer State park, headed up to the Michigan Peninsula to Pictured Rocks and then back down to PA for a stop at Ohiopyke for the natural waterslides. My younger kiddos had a great time after they dropped their sister off. Before we dropped her off, we did do a stop at Arches National Park, which if I recall was about a day or 2 drive from USAFA.
Looking forward to hearing what you end up planning.