Overlook just east of the continental divide.

Three general observations after a week on the Great Allegheny Passage and C&O Canal towpath:

• Six days would be perfect; the five-day schedule offered insufficient recovery/slack time and left me feeling rushed, despite good stretches at 15+ MPH. In my case, a rainy morning and the Fallingwater side trip ended up taking up a good chunk of day two, which left me with almost a century to accomplish on day three. Plus, the towns were more interesting than I expected.
• For the most part, you actually might not want to stay overnight in the most interesting towns (IMO: Ohiopyle, Cumberland, Harpers Ferry). Their attractions are mostly open during the day, whereas for an overnight location you mostly just want to eat dinner and crash. Specifically, I’d recommend stopping at Harpers Ferry during the day when the historic park’s attractions are open, then overnighting at Lockhouse 28, and then a leisurely reintroduction to metropolitan civilization the next day.
• The C&O’s surface varies tremendously. Some of the sections are, like the parts closest to DC, very rocky and tough to take at speed, but others are much smoother (and often muddier). I did appreciate taking breaks from it, though.

The daily itinerary, as it played out:

1. Pittsburgh to Ohiopyle, Penna. 77 mi. slightly uphill via McKeesport, West Newton, Connellsville. Stopped at Target in Homestead to buy a $30 tent, which did in fact pay off. Some of the Steel Valley towns would have been worth a side trip, but the main goal was to get out of town. Highlight: Appalachian Juice Company in Connellsville.
2. Ohiopyle to Meyersdale, Penna. 42 mi. uphill via Confluence, Rockwood. The morning trip to Fallingwater was very steep: it’s 780′ of vertical over less than five miles. By comparison, the GAP’s first hundred miles rise by about the same amount. I’d planned to make it over the divide to Frostburg, but had to stop 15 miles short once night fell — it’s really, truly dark. That said, Fallingwater is truly transcendent.
3. Meyersdale to Hancock, Md. 93 mi. mostly downhill via eastern continental divide, Cumberland, Paw Paw. Detour onto Western Maryland Rail-Trail. Highlight: dinner at Buddy Lou’s in Hancock.
4. Hancock to Sandy Hook, Md. (Harpers Ferry) 48 mi. flat via Williamsport, Sharpsburg. Detoured over land from Williamsport through Antietam Battlefield. This cut out about 16 miles by keeping us away from a particularly windy stretch of the Potomac; plus, the main uphill was from the valley up to Williamsport, where we were stopping for lunch anyways. Highlights: lunch at Desert Rose Cafe in Williamsport and Nutter’s Ice Cream in Sharpsburg. However, we did end up bypassing Shepherdstown, W.V., a town that other riders commended.
5. Sandy Hook to Reston, Va. 45 mi. via Leesburg, switching to W&OD via White’s Ferry. Took the Silver Line to Washington Union Station from there. Highlight: ultra-smooth cold-brewed Hopscotch Coffee. Although this was the only day that passed by any breweries (Crooked Run, Old Ox, Lost Rhino, Mad Fox, Bluejacket, etc.), we were in too much of a hurry for any stops.

Update, 1 June 2015, for benefit of whoever landed here searching for a five-day itinerary: Finished another trip last week. This itinerary was more balanced miles-wise, owing to an evening rather than midday ending on Day 5. Three nights of camping also helped keep the itinerary more flexible:

1. Pittsburgh > Braddock > West Newton > Connellsville 59 mi. Camped behind a supermarket (24-hour!) at the edge of town in Connellsville, which was convenient if not scenic.
2. Connellsville > Ohiopyle > Confluence > Rockwood 47 mi. Lunch at Ohiopyle was a perfect “last stop in civilization.” The surroundings get very rural past there, but Rockwood did at least have pizza and campsites.
3. Rockwood > Frostburg > Cumberland > Lock 62 campsite (past Paw Paw) 72 mi. Frostburg is empty after the college lets out. Stocked up on supplies in Cumberland ahead of the only night of primitive camping.
4. Lock 62 > Hancock > Williamsport > Sharpsburg > Shepherdstown 74 mi. Shepherdstown was a better overnight stop than HF, with better nightlife even when school’s not in session.
5. Shepherdstown > Leesburg > Herndon 55 mi. Spent a while lingering around Harpers Ferry during the day. Took the 5A from Herndon-Monroe rather than the Silver Line because it was rush hour, and got a warning from the bus driver about our front racks not fitting — but we were fine.