This story has nothing to do with the 2025 TransVA Grand Depart, but that’s where the story starts nonetheless. It was late in the day of the 2025 TransVA grand depart when I pulled up to the Graden Market, 110 miles into my ultimately failed attempt number two at completing the Mountain 565 route.  Sitting on the floor in the shop was a fellow TransVA rider, eating pizza and talking with a third TransVAer.  Grubby and tired after nearly a hundred miles of hot, humid gravel, the young woman told me she was on her way to Washington, and that her plan was to ride straight through without sleeping.  That’s pretty badass, I thought to myself, as I wished her luck and got back on my bike.  My next thought after that was “someday, I’d like to do that.”  I also remember thinking that doing the 200 miles straight through was near impossible, at least for me.  Which it wasn’t, given that I’d done longer rides in the past.  But like I said, it was late in a hot, humid day and we were all tired and not thinking entirely straight.  I turned down the kind offer to share some pizza and got back on my bike.

Ten months later I changed my mind and decided it was time to try a DC-Harrisonburg non-stop myself.  Winter was coming, and even in early October the nighttime temperatures dipped to near freezing.  I figured I had to do it now or wait until spring.  So, on a Friday afternoon after work, I loaded up on drinks at the Subway next to my office in downtown DC and took off.

My plan was to follow the TransVA route to Harrisonburg, but I cut a few corners to save time.  I took the paved W&OD to Purcellville rather than follow the C&O canal.  This cut about 20 miles from the route, and gave me a lot more options for stopping to refuel and warm up along the way.  It also saved me the pain of riding some chunky gravel along the first 15 miles of the C&O.  I had ridden the path a few days before, and it was rough.

A few miles up from the Potomac, the trail flattened out and I made good time to my first stop, an Exxon station next to the W&OD in Leesburg.  The ride out there was boring.  If you think the W&OD is dull during the day, try riding it at night when all you can see is the dotted line down the middle of the path, along with the occasional critter scampering across the path.  Along with the animals were a few walkers or cyclists, many of them without any kind of lights or reflective clothing.  So, if you take to the W&OD at night, bring a good headlamp and keep your eyes on the path ahead.  And if you like walking on the W&OD at night, for God’s sake put on a reflective vest or one of those LED singlets.

Three hours or so into the ride I reached the end of the W&OD in Purcellville.  A few blocks later I pulled into the 7-11 on Main Street – the last open store on the route until Larkin’s Grocery, a good 90 miles down the road.  I was hoping to find an apple fritter and fill my bottles with a little extra to get me through the night.  Sadly, they were out of apple fritters, so I settled for a glazed donut, a Pepsi, and a lot of water and Gatorade.  And a pair of white tube socks.

My Tailfin Aeropack was stuffed with everything I could think of to keep me warm, but I had forgotten one thing – shoe covers.  Luckily, the 7-11 had large tube socks, so I got a pair and sat on the curb outside the store while I pulled the socks over my shoes and then cut holes in the bottom for the shoe cleats.  They looked idiotic, but they worked – my feet never got cold.  And, at $5 for two pair, way cheaper than the Castelli shoe covers I usually use.

Now past 10 pm, it was getting steadily colder.  But as long as I kept moving, I was ok.  Every time I stopped for more than a minute, I would start shivering.  In Purcellville, I pulled on my neck gaiter and warm gloves, but left the leg warmers and jacket in my pack.  Finally. around 2 am I stopped at the Old Zion Church, right on the route on Zion Church Road just north of Front Royal.  Back in May some generous trail angels, Paul and Kim, had set up a well-stocked aid station here for TransVA riders under the church’s outdoor pavilion.  But now, it was just me and a few brave moths who kept dive bombing my headlamp as I sat on a picnic table and put on my leg warmers and jacket.  What kind of moth still flies around when it’s 42 outside?  I started shivering almost right away, but once I got back on the bike again it was ok.

The next 30 miles was a half-paved, half-gravel endless series of rolling hills, adding up to a steady but barely perceptible rise.  For nearly the entire time, it was just me and an odd mix of unidentified, furry beasts that skittered across the road or looked at me from the bushes, unseen except for their glowing eyes.  They could have been foxes, cats, weasels, raccoons, bobcats, rabbits, elves, trolls, wombats, or something else.  The only animals I saw clearly were the deer and the rabbit I came within inches of flattening on a gravel road not far from the Old Zion Church.  For the next four hours I saw almost no cars, and didn’t pass through any towns.  If you want solitude, you’ll find it on this route in the middle of the night.

There’s something I love about riding all night.  Even at 50+, there’s something about it that feels illicit and rebellious.  It takes me back to when my friends and I would sneak out of the house at 3am to wander around Sioux Falls, running to hide in the bushes every time a car drove by.  I also just love the solitude, the black and quiet of the deep night broken by nothing but the sound of my tires on the gravel.

Around 4 am is when I really started to drag.  In addition to forgetting my shoes covers, I didn’t bring enough caffeine.  The matcha tea packets I had normally give me a good kick in the ass during the day, but on this night they weren’t cutting it.  I thought about pulling over and sleeping for a few hours, but didn’t like the idea (meaning I couldn’t bear the thought of) setting up a tent, inflating a sleeping pad, etc.  So I pushed on.  The riding itself wasn’t hard, but sleep deprivation makes even the simplest things harder.  Even small hills became a mental chore.

Then there was the added hassle of having to constantly take clothes off and put them back on to avoid overheating or freezing.  At the bottom of the climb up to Fetzer Gap I stopped and took off my jacket and heavy gloves, then started the steady, 2-mile climb up.  This was my kind of climb – long and steady on decent pavement.  The 8% grade was tough enough to be interesting, but not hard enough to force me to walk or start crying.  Near the top a car came around a bend, the driver probably muttering to himself about what kind of jackass rides up this climb in the middle of a cold, dark night?  At the top of the climb I stopped again, got dressed up, then eased my way down the other side.  During the day this is probably a fun descent to bomb down.  But in the dark, all I could think of as I rode the brakes down the hill was me losing control and plunging over a guard rail and down the side of the mountain.

The climb and descent definitely woke me up, but within a few miles the effect wore off and I was again desperate for sleep or caffeine.  But instead of a 7-11 or bed, it was the sun that gave me a reprieve.  Around 6:30 am I noticed the first bits of light on the horizon, giving me an instant jolt.  I was also on a steady downhill towards Columbia Furnace, where I knew there were stores that were open.  When I turned a corner and saw Larkin’s Grocery just a quarter mile ahead, I told myself that I had survived the worst of the ride.  Like most gas stations in the Shenandoah Valley, Larkin’s has a grill.  The very sweet woman behind the counter called me “honey” and made me pancakes, sausage, and hashbrowns.  I stood at the counter (the only seating is outside) and ate my breakfast with some weak coffee.  The guy at the front register said he was just getting into cycling and asked me a lot of questions about bikepacking.  With all the food, good company, and warmth I didn’t want to leave, but after almost an hour I reluctantly filled my bottles and got back on my bike.

The next thirty miles were the hardest of the route.  The gravel was smooth and the climbs (except one, more on that later) were reasonable.  The scenery was great.  Maybe it was the lack of sleep making everything feel harder than it was, but this 30-mile stretch felt like an endless series of small climbs.  And in a sense it is – in the thirty miles after Columbia Furnace you gain 2800 feet in elevation.  The average grade is only .8%, but I couldn’t help feeling like I couldn’t find a flat section or downhill for hours.  Just before one of the climbs I finally took off my jacket, leg warmers, and DIY shoe covers, mainly so I didn’t burst into flames on the climb.

The long slog upwards ended with a real doozy finish, but I can’t say I wasn’t warned.  About five miles past Basye is a hill David Landis marked on the map as a “steep wall climb.”  He’s not kidding.  I started climbing the gravel hill and was soon giving it everything I had just to keep moving.  I looked down at my Garmin – 21% grade.  I looked up and couldn’t see the end of the climb, so I got off and walked up the rest of the hill.  The steepest part of the climb was less than half a mile long, but I know my limits – I’m not too proud to push.  With the climb over I came out onto a three-mile long plateau with gorgeous fall views in every direction.  The roads were good and I finally felt like I was making decent time again.

About five miles later I hit another steep-ass climb, forcing me to push again – but just for a few minutes.  By now I could smell the finish, and that powered me through the ever-worsening fatigue.  By now, I’d been awake for more than 30 hours, and no amount of coffee could keep me feeling good.  Although I felt physically strong I was ever more wobbly mentally, and the small rollers between me and the finish were a mental drain.  My legs still felt good, but even dinky hills felt like torture.  I just wanted to be done.

The route smiled upon me, however, and except for one more longish climb the final 20 miles were mostly downhill (but with plenty of annoying rollers thrown in for not fun).  Around 3pm I finally rolled up to the finish line at the Rockingham County Courthouse.  There I met Carolyn and Cee, who had just finished the Harrisonburg-DC loop.  Whereas my wife and the good people at Larkin’s Grocery thought I was crazy for doing this whole ride in one go, Carolyn and Cee – in the way only a fellow bikepacker could – understood why I rode all night to get here.  We took some pictures together and talked about our bikes before rolling off in separate directions.  My wife picked me up in the car a few minutes later, and we celebrated by going to Buc-ee’s for enormous bbq sandwiches and fudge before driving home – a decadent and fitting end to a great ride.

A few notes on equipment:

• Tires – Specialized Pathfinder Pro 38mm – they were just right for the gravel sections, and feel fast on the pavement
• Gearing: GRX 1x, with a 38 tooth Wolftooth chainring in front and an 11-46 cassette in back.  The gearing worked well for me this time, and when I did the whole TransVA Valley Route in May.
• Lights: I have Son Delux dynamo hub, powering a Sinewave Beacon headlamp.  I have another light mounted on top of my helmet – the Sinewave is more than enough for night riding, but I love having the additional light on my helmet.  Having the light move with your gaze is great when you’re trying to spot critters in the bushes at night or find things in your bags in the dark.
• Bags: I love my Tailfin rack and cargo bag – more than enough room to stuff extra winter clothes.  My only complaint is that you can’t stuff things into the bag while you’re moving, but the new Tailfin cargo bag with mesh pockets on the sides might solve that.  Or, I could have just put a largish bar bag on the handlebars.