Places worth a stop: Eastbound

Terminus: Pittsburgh, PA - Mile 0

A vibrant city, but if you arrive on that early morning greyhound you will be disembarking at dawn. The station is in the northern section of downtown and about ½ a mile away from the start of the trail. Head south down Liberty/Grant Ave until you hit the bike trail along the Monongahela River, turn east into the rising sun, cross the “Hot Metal Bridge” and you will be on your way. You may have to get creative in finding a place to throw away the rather large bike box that is now useless.

Camp One: Connellsville, PA - Mile 60

On your first day you will start in the metropolitan downtown of Pittsburgh and ride out into the wilderness, passing old suburbs and industry towns in the pits of metamorphosis. There is nothing too special about Connellsville, but it is a good target to pass before the end of your first day. Connellsville is home to some easy country restaurants and there is camping available right as you ride into town. I’d recommend getting a hot meal here to reward your first trail day, quickly resupplying, and tacking on a few more miles if you have the energy and daylight. You can find some lovely wooded spots to pitch your tent outside of town if you are creative and don’t mind a little solitary dry camping.

Point of interest: Ohiopyle, PA - Mile 77

If you don’t mind putting in a few miles before breakfast, or putting away extra miles on Day 1, Ohiopyle is a charming town to spend some time in. Many old-timey restaurants and Bed and Breakfasts grace this town, since outdoor adventurers have been visiting here for decades to bask in the exquisite surrounding nature and watch the Youghiogheny River tumble down the beautiful Ohiopyle Waterfalls that bisect the town.

Camp Two: The Eastern Continental Divide - Mile 124

Elevation 2,392 feet. The tallest on the trail, and the beginning of the most glorious downhill you’ll find on your journey (if you take the trail eastbound). Grab dinner in Meyersdale ten miles prior and camp a little past the peak to wake up to few miles of gravity doing your work for you. Bask in the views, and pedal like hell through the Big Savage Tunnel, the longest on this journey, cutting directly through a mountain for 3,294 feet. It is an easy coast from the divide to a good breakfast in the town of Frostburg, and then on to the trail merger at Cumberland, Maryland.

Point of Interest: Cumberland, MA - Mile 148

Cumberland is the merging point of the GAP and C&O trails, as close to a satisfying halfway point as you will get, though you still have about 185 miles left to go. You’ll probably get to Cumberland a little too late for breakfast and much too early for dinner, but if you hurry, or don’t mind being late, you can grab an early lunch in the quaint downtown before starting on your new path, the C&O Canal. The C&O is much more rustic and sparsely populated than the GAP, so definitely resupply fittingly.

Camp Three: Little Orleans, MA - Mile 192

You should have found out by now, that the C&O is a whole different beast compared to the GAP. While it doesn’t feature any insurmountable obstacles, the crushed limestone path is a little bumpier, and towns are few and far between. This also makes for more efficient biking and less distraction from nature. The environment around this trail is spectacular, and there are a lot more rustic resources here than on the GAP. You will pass a biking campground with a hand-pump well and fire ring every five miles or so. And the towns, while small and spaced out (like Little Orleans), will feature places to resupply and eat. You’ll either need to pedal hard or keep yourself well supplied to make up for the different distribution of resources.

Camp Four: Shepherdstown, WV - Mile 261

While not technically on the trail, Shepherdstown was my favorite trail-town of the trip. It takes a little more effort to get to, since you have to cross West Virginia on an elevated bridge over the Potomac, but it is well worth the extra effort. If you have the energy and daylight I would recommend biking in for a beer and the end of the day meal at Maria’s Taqueria. The downtown is a unique vestige of trendy small town America, and home to many a good bar and restaurant. There are an abundance of lodging options as well, if you want to spend your last trail night in a bed, but I wouldn’t recommend giving up on your camp so soon, the section of the riverside trail between Shepherdstown and Harpers Ferry is especially beautiful.

Point of Interest: Harpers Ferry, WV - Mile 273

Dinner in Shepherdstown is made complete by breakfast in Harpers Ferry. The historic town is best known for being home to the arsenal that John Brown raided in order to fuel his failed 1859 slave revolt, but sitting on the confluence of the Potomac and Shenandoah rivers - whose merging point serves as the border between Virginia, West Virginia and Maryland - has made Harpers Ferry an important location for most of American history. The town and its surroundings are quaint and beautiful, if not a little touristy, but definitely a great place to pick up a country breakfast before starting your final push to DC.

Terminus: Washington, DC - Mile 334

The eastern terminus of the trail, Georgetown, the finish line. The canal ends at the waterfront where freight was originally swapped between seafaring ships and the mule-hauled barges. Today, Georgetown is one of DC’s most vibrant neighborhoods and cultural centers, be sure to grab an overpriced beer here to celebrate your victory. About 12 miles before you cross over the final stop you will hit Great Falls, the most majestic water feature on the trail. Be sure to take a quick stop to take in the category 5 rapids and falls as the Potomac drops 77 feet in less than a mile.