Sometimes the path you’re on feels like it will never end. Your seat feels like a column of marble. Your legs feel like they’re gelatinous. Your skin, your legs, and your lungs, all burn for different reasons. If you’ve ever felt this way, then you may have been on a long-distance bike trip. If these symptoms seem familiar then you’ve known the struggle, but you might also feel a subtle grin blossoming right about now, as memories of one or more such trips flicker back, painlessly.

David, in his “ Younger Years,” at Harper’s Ferry.

I began regularly taking long-distance bike trips in 2012 when an in-shape friend with a bike told me about the Great Allegheny Passage (GAP) and asked me if I wanted to go. Of course I did, I was in. No matter that I didn’t have a bike, hadn’t really biked for 15 years, and wasn’t in any shape to tackle 335 miles in four days (83.75 miles per day). Those minor details would be worked out later, the siren call of this epic and historic trail had captured me, and I was going.

I acquired a bike for free, a used no frills Trek 930 built in 1997. After a few training rides and adjustments (seat, neck, pannier rack, etc.) it was ready to go (I still ride it today). Gliding along the Anacostia River trail from my home in the Brookland neighborhood of DC, chasing sunsets at Lake Artemesia in College Park, I really felt like I could do it, I could ride from Pittsburgh to DC and camp out along the way. A training ride out to Harper’s Ferry and back disabused me of that notion; an old ankle injury led me to believe it would be too much, so I settled on Rockwood to DC, 219 miles in three days, skipping the 105 mile slow climb out of Pittsburgh (and 1.5 days). My friend did the entire thing, we connected in Rockwood and went the rest of the way together.

Hurricane Sandy required a late season start and there was already snow!

This was two weeks after hurricane Sandy (our original schedule having been right when Sandy hit). There was snow on the ground, very few people, and most places closed that catered to the trail. Twice we had hostels to ourselves. It was perfect. Endless miles of only hearing the occasional bird and the rustle of your tires on fine gravel. Of mountains and streams, farms and woodlands. The struggle was real, and it was worth it. Camping alongside a river, startling a bald eagle into majestic flight, rolling into small towns you’ve never heard of and quickly forgotten.

Yes, the downhill to Cumberland is as fun as it looks.
The tunnel at the top.

The routine of the pace is relaxing, just absorbing whatever the next curve presents as you quietly pump your legs up and down, over and over, like an oil rig of necessity. Time is your only friend and your only enemy; the need to keep going and beat the sunset to your destination; the lack of any desire to do so lest you miss something. As you may have gathered by now, for me it’s all about the journey. I want my bike rides to be relaxing, enjoyable, memorable. Sometimes, yes, they can be a struggle, depending on equipment failures, terrain, weather, sheer distance; but the goal is the experience of the journey, not the destination.

Since that original trip, my friend and I have completed the journeys listed below and enjoyed every one. Keep reading and consider if one of these might be for you.

Greenbrier River Trail – Maybe the most beautiful of them all, this trail is the longest of its kind in West Virginia. Once a C&O rail line, the Greenbrier River Trail follows 78 miles of the longest free-flowing river on the east coast. The trail provides many breathtaking views as it passes through several small towns, crosses 35 bridges, goes through two tunnels, and cuts through some of West Virginia’s most remote areas.

I’ve done this trail twice, most recently in September of 2023, and it was amazing both times. Camping in this area in the late summer is perfect, swimming in the river is wonderful, and the changing trees call your eyes upward with every turn.

Lush forest with river views the entire time.
Sunset over the swimming hole.

Richmond to Williamsburg Century Ride – Virginia Capital Trail This is a very pleasant trail, given that it’s entirely paved, and there’s quite a bit of history along the way. I wouldn’t call the scenery all that interesting, but if you’re looking to bag a century in a day, it’s hard to beat.

Virginia Capital Trail trailhead.
Along the Virginia Capital Trail.

C&O Canal Path to WO&D Century Ride No longer possible given the closing of Whites Ferry (insert sad emoji). This is a great training ride given you’re never very far from civilization. Definitely more populated than many other rail trails, but it makes up for this drawback by being very close and easy to access from anywhere in the DC region. Some sections are paved, and most of the rest are well maintained.

Baltimore to York Overnight Out and Back Take the train to Baltimore from DC, bike to Cockeysville, MD, and get on this 40-mile gem to York. Camp out and ride back. Plenty of water features, farmland, and woodlands. Nice trail, relatively easy grade, beautiful country to bike through.

Forest, fields, farms, and streams abound betwixt York and Baltimore.

Delaware Canal State Park Trail Number two on my list of most beautiful, this easy (very flat) trail along the Delaware River was quite the experience, given that it rained day one, temps dropped, and we had a serious breakdown. Given the time of year (late fall) we rode in the dark pouring rain for what felt like ages. We made it to Easton alive (60 miles) and were succored back to health by the most endearing British-American woman you’ve ever met (AirBNB host). The next day was perfect for the ride back, and we have some amazing memories. The colors during the fall leaf change were epic, small town shops and restaurants were a definite bonus and something you should leave time for.

Fall colors, cool temps, cool gents.

Cumberland to DC Take the Amtrak out and ride back, this 100 mile ride takes you back through American history along the rivers. An easy grade, plenty of campsites, and just the right amount of distance for two days of riding.

Harper’s Ferry overnight out and back This is a very doable ride in two days at a leisurely pace. Harper’s Ferry is very beautiful and has so much history to explore. Long enough to test your mettle and your equipment, make sure you have enough water with you during the winter, as the wayside water pumps get turned off. (Note, a recent 20-mile jaunt with the kids to Brunswick found the well water labeled as no longer potable!).

Shepherdstown overnight out and backAdding some miles to the Harpers Ferry version, this ride takes you a bit farther to another historic town. Plenty of campsites and water and beautiful vistas along the river. Very peaceful and quiet between Harpers’ Ferry and Shepherdstown with less people overall.

Regardless of your tolerance for pain, level of fitness, or biking acumen, I encourage everyone to try it at least once. Bike somewhere far, really far, spend the night, then come back. Maybe take a train somewhere with your bike and come back. Everywhere is biking distance if you have the time! You’ll (eventually) forget the muscle pain, the sunburn, the dehydration. You’ll remember the culture, the wildlife, the smells, the people you meet, the sense of accomplishment, the wonderment of that vista that can only be seen if you biked that far on that day.

Recommended Equipment

  • First off, you don’t have to spend a lot of money to make this a reality. A simple bike with some simple gear should cost no more than $500. And if you buy stuff a little used it can be much less.
  • Mountain bike or hybrid. A mix of utility, comfort, and durability is the goal. You don’t want shocks, although a suspension seat post is a nice addition.
  • Repair kit with extra tubes and patches. You can go years without a single flat, and then get three in a day (like me!), be prepared.
  • Racks! Depending on the length you’ll need more racks, then add paniers to carry stuff. For most rides a single rear rack with a double panier will be sufficient.
  • The right clothing, footwear, glasses, and protection from the elements. I’ve had a bug stuck deep in my eye socket, felt like I was going to die from humidity, and shivered in the dark under a bitter driving rain. You don’t want those times to be the times you regret spending a little bit more for something that offers more protection.
  • Last but not least, relish the moments. The trail is like a spa for your mind. We’re blessed with a ton of a great trails in the Mid-Atlantic so take advantage. Even if things go terribly wrong, you’ll have memories of both overcoming hardship and the journey itself, you won’t regret it.