Completed my GAP and C&O ride last week and thought I'd share my experiences.
I took Amtrak from Denver to Pittsburgh with a transfer in Chicago. It was $100 for the ticket and then $20 for the bike roll on service ($10 for each train). 30 hours but cheaper than flying and didn't have to deal with the hassle of dismantling my bike.
I had a lot of time so it was nice relaxing. My longest day was only 60 miles.
Day 1: Pittsburgh ----> Buena Vista: The GAP starts at Point State Park, a short distance from Amtrak. Camped at the Dravo Cemetery. Free hiker/biker sites with well water and vault toilets. Fire rings with free firewood also available. They had 3 or 4 wooden shelters for tents and plenty of grass/trees for tents/hammocks.
Day 2: Buena Vista ---> Ohiopyle: Camped at Wilderness Voyageurs. They offer free camping for hiker/bikers in the pavilion behind their business. I used their pavilion to hang my hammock .They have a bath house with free hot showers. It's open 24 hours but they don't have electricity. If you're going east it'll be on the right BEFORE you cross the pedestrian bridge into town. If you cross the bridge you can turn left onto the highway and cross the auto bridge and it'll be on your right as soon as you cross the train tracks... Speaking of which, if you're a light sleeper I wouldn't stay here. The camping is 10 feet from very busy train tracks. They run all night long and blow their horn 4x and it's on a curve so their wheels screech. It didn't bother me though.
Day 3: Ohiopyle ---> Meyersdale: Camped at the Maple Festival Grounds in town. $15/night. Hot showers, bathrooms with electricity, pavilion for hammocks and a huge yard for tents. The pavilion and stage have lights and electricity. Free firewood as well. WiFi works but not the strongest signal. This place is only available when the grounds are hosting the Maple Festival or other local events so be sure to check the calendar or call ahead.
Day 4: Meyersdale ----> Cumberland: Camped at the YMCA, a mile off the route on a busier road. $12/night. You have full use of the YMCA until they close at 10pm. Showers, bathrooms, pool, basketball courts etc. WiFi is pretty crappy. Pavilion with electricity and poles to hang hammocks. Large grass area for tents. Much like Ohiopyle, this is right next to the train tracks BUT they don't run as often and they're much quieter.
That's the end of the GAP. The trail was amazing... That's where the nice trail ends and the C&O begins.
Day 5: Cumberland ----> Hancock: Camped at C&O Bicycle. $15/night gets you a hot shower, WiFi, outhouses, a place to wash your bike (you'll need it if it rained recently), lights, power outlets and a bunk in their "chicken coop" behind a locked gate right off of the trail. Their "chicken coop" is a screen off area with ~20 beds (10 sets of bunks). Mattress pads provided. The C&O was really muddy this day.... We rode the paved Western Maryland Rail Trail (WMRT) the last 10 miles to Hancock. They're building more access points on the C&O to the WMRT so soon you'll be able to ride the last 12 miles to Hancock.
Day 6: Hancock ---> Harpers Ferry: Rode the WMRT until about a mile before it ended (the last access point to the C&O) and dealt with the mud until Williamsport. I wanted to see Antietam Battlefield so in Williamsport I jumped onto local highways to get to the battlefield. It was a nice change of scenery and vehicle traffic was minimal. A bit hilly and shoulderless in places but a great ride. Stop by the visitor center in Brunswick for detour directions if it's still closed. I got back onto the C&O at Dam #4. The C&O between Williamsport and Dam #4 was, at the time I was there, one of the worst sections. That played into skipping that section too. The last miles to HF were nice and not too muddy. I spent 2 nights at the Harpers Ferry/Civil War Battlefields KOA. It was extremely expensive. $65/night. Nice for hammocks but their tent sites are on a hill. They don't enforce quiet hours and overall it was a miserable experience. I spent my day off touring the Harpers Ferry National Historical Park. $5 entrance fee for pedestrians. It was worth the day off.
Day 7: Harpers Ferry ---> Leesburg: Rode the C&O to Brunswick where the trail was closed. The official detour to Point of Rocks was along hilly country roads (nothing more than a 5% grade) with okay shoulders and minimal vehicle traffic once you leave the city. The C&O from Point of Rocks to Whites Ferry was the best section of the trail IMO. At Whites Ferry I took the ferry across the Potomac ($2 cash only fare for pedestrians) to Virginia. It runs 365 days a year unless the Potomac is flooded from about 6am to 10pm. Highway 15 was a nice ride into Leesburg until it spilt to the regular highway and the business route. The shoulder here disappears and the fog line becomes the shoulder for about 500 feet in the VERY heavily used stretch of highway. I waited until there were no cars coming and gunned it. Stayed the Red Roof Inn on Market St. $75/night in a newly remodeled hotel within walking distance to everything the town has to offer.
Day 8: Leesburg ---> Washington DC: Part of the reason I chose the Red Roof Inn was because the Washington & Old Dominion Trail (W&ODT) runs right behind it. The W&ODT is a paved trail that runs between Purcellville and Arlington. I rode this to Arlington and it was great. It's heavily used and towns are no more than 10 miles apart. In Arlington where the train ends you have to cross the street and go to your right. From there get onto the Four Mile Run Trail and follow the signs for the Mt. Vernon Trail. Once you're on the Mt. Vernon Trail follow the signs for Washington DC. It'll take you across the Arlington Memorial Bridge and drop you off right next to the Lincoln Memorial. A friend of mine lives in Dupont Circle in DC and that's where I stayed for 2 nights before flying home out of BWI.
Happy to answer any questions etc!