Skyline Double

I’m convinced that Skyline Drive is the best place on the east coast to ride a road bike. For starters, the surface is sublime. You roll with little resistance and the chatter is kept to a bare minimum. And for a 104 mile road that travels down, up, and around mountains, it is engineered perfectly. The grade is challenging, but not too steep, and the curves are all banked so well that you rarely feel yourself terror-braking on the descents. Then there is the traffic, or rather, the lack of traffic. Other than peak foliage season, cars and RVs and motorcycles pass at a reasonable frequency and distance and adhere (mostly) to the posted 30-35mph speed limits.

Then there are the views.

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Sunrise and sunset (pictured) are predictably stunning. The panoramic views of the Shenandoah Valley are beautiful. And it seems like there is a scenic overlook at the top of every climb or the sweep of every curve.

If you’ve ridden there, you know all of this and you probably can’t wait to go back. I had the good fortune to get out there four times last year, and each time was better (and longer) than the last. All winter I daydreamed about going back and soaking in as much of the route as humanly possible. Of course, the best way to do that would be to ride the whole thing, but that puts you 104 miles away from your car, which means you need to grab a hotel in Waynesboro and ride back the next day.

Solution: just ride back the same day!

I didn’t find many takers, but a few cyclists with whom I have ridden stupidly long rides, Eric Williams and Dana Wise, were up for it. With an agreed upon wheels-rolling-time of 6:00am, we instead pushed off at 6:21am on Saturday morning because I am an infant and incapable of getting to any ride on time.

That was okay, because as we made it up the first climb – the ascent to Dickey Ridge – we were treated to the beginnings of a beautiful sunrise.

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The wind and cold were really bad for the first few hours and played havoc with our descents. I even got the dreaded wobbles going down one descent, spooking me enough to ride the brakes for a while until it warmed up and calmed down a little bit. Of course that didn’t really bother Eric or Dana and they just bombed every downhill we came upon proving once again that I am terrible at bike handling.

Another nice feature of riding Skyline is that the waysides are spaced pretty evenly apart. Big Meadows (we arrived at 10:03am) is easily my favorite and it’s halfway to the halfway point, which makes it…something. They also have excellent big breakfast sandwiches and if you are going to do any kind of reasonable ride, breakfast sandwiches are an important component of success. Of course, it’s a Big…Meadow and the wind is whippier and colder up there and the restart always kind of sucks on spring days.

Still, we were feeling pretty great and half an hour later we headed out. With the wind having died down, we tucked and flew down the hills and then ground up the climbs. It was just the best that Skyline has to offer with the vistas and wildlife and fresh air. The alternating surges of euphoria and adrenaline are absolutely addictive.

We rolled up to Loft Mountain wayside at 12:08pm, which was about mile 78. As full as I had been after Big Meadows, I suddenly felt like I hadn’t eaten anything at all. I ordered a king sized Payday and wolfed it down with a large gatorade and immediately felt better, mostly confirming my suspicions that I will get rich when I publish the Convenience Store Diet book in 2018. We were making great time and were less than 30 miles away from the southern entrance to the park – which is where we would pack it in for the day turn around and head back the way we came!

Clothing-wise I had been heavily layered to this point. Wool long sleeve baselayer, merino sweater, light windbreaker, merino wool gaiter, skull cap with ear flaps, wool cap, knickers, shoe covers. Most importantly, I had the appropriate Ridge Supply Skyline – Pink socks on.


It was now warm enough to remove the windbreaker and that carried me through to the southern entrance station at Rockfish Gap. At 2pm I arrived a few minutes before Dana and Eric (because I am a terrible teammate) and set my bike down against a storm drain and sat down. Suddenly I felt extremely fatigued. 104 miles and 11,000 feet in the bag and I was wiped out. I don’t remember if I even ate anything sitting there, but I started to get cold again and for the first time wondered if I was going to make it back to the start. OH MY GOD I AM GOING TO DIE OUT HERE. Then a few cars drove by and I pulled it together.

Dana and Eric rolled up minutes later, made a u-turn at the ranger station, and my whole mood immediately changed. It was like I hadn’t seen them in months. Yes, I am unstable.

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Eric took a quick pic of me laying in the storm drain (because I looked like an idiot), but since there were no services here we didn’t really treat this as a rest stop and pushed on. I still had more than a bottle of water and we all seemed to be in pretty good shape for the two hour trip back to Loft Mountain.

We continued north to a familiar pattern. I would lead up the hills, Eric and Dana would catch and pass me on the downhills. By the time we got to Loft Mountain, at around 4pm, I was beat. I grabbed a cup of coffee and a pack of aleve and a king size payday from the restaurant and went to lay down on a picnic table. With a double metric already in the bag, Dana and Eric were pretty tired, too. Dana took some of my aleve and they both ate and I tried not to move. I was feeling all of my 46 years. What the hell was I thinking? This was hard. Whaaaaa. Dear god I was annoying myself just having to listen to my internal monologue.

I wasn’t really in pain, just worn the fuck out. We ended up spending an enormous amount of time there – 40 minutes and I don’t know that I felt all that great when we left. But we didn’t have a choice.

That’s the beauty of this ride. You don’t really have a choice but to keep going. Your car and your loved ones are too far away to do you much good. Outside of a medical emergency, your legs are getting you home and that’s that. So you make peace with that and you keep moving.

I was a little worried that we weren’t going to make Big Meadows before it closed. Eric was not feeling tip top (none of us were) and we only had a little over two hours to get there before the wayside closed. Getting there and having it be closed? That would be bad.

As I crested the hill with about 15 minutes to spare, the site of Big Meadows was beautiful. If I wasn’t so old and dehydrated I would have cried.

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We were able to get inside and order food but they were closing the restaurant and wouldn’t let us sit down. So I headed outside to eat what I consider the absolute best bike ride food I have ever had in my life. Warm blackberry cobbler with blackberry ice cream. It’s an underrated super food and the fact that you can get it to go in a white trash styrofoam fast food container makes it even better. The container is so white trash that I will fight you if you don’t agree with me.

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The cobbler was the good news. The bad news was that it had gotten too cold to eat outside. So I brought it back inside and ate standing up. Eric was struggling with digestive issues, I was freezing, and Dana was popping aleve like a ritalin-addicted rich kid. We were not a pretty sight. As is the case with most long rides, I eventually ended up in the bathroom shoving my hands against the hand dryer for a selfish amount of time.

At 7:15p we finally got our act together and headed out. Except there was a problem. I had stepped in some soft dirt and jammed up my cleat on the bottom of my bike shoe and couldn’t clip in on the left side. I have speedplay (lollipop) pedals which are basically impossible to pedal if you aren’t clipped in. I was embarrassed enough that I didn’t say anything to Dana and Eric as they took off down the drop that leads north from Big Meadows. I tried to follow them, unclipped, but started to wobble and freaked the fuck out. They disappeared in the distance and I pulled off at an overlook to look for a stick to try to dig out my cleat. After what seemed like an eternity (non dramaboy time five minutes) I was finally able to get everything cleaned out enough to clip in. Eric and Dana were long gone.

This was the low point. The sun was setting, I was freezing cold, and I assumed I wouldn’t see my guys again. You have this point in every stupid long ride or run, a point where it just sucks. This was it for me. I decided to just focus on what I could control, which meant getting warm by grinding it out as hard as I could on the uphills and generate enough heat to keep me warm on the flats and descents. Plus I had the sunset and that always cheers me up.

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That actually worked and after a while I came upon Eric and we rode together to the top of a climb where Dana was waiting. At this point we had about 30 miles to go and two hard climbs – one of which was Hogback, a name which does not do it justice.

At this point it was dark but the bright moon and stars were out and the Shenandoah Valley was glittering with lights. I kept reminding myself that despite how destroyed I was, I needed to soak this in and retain it. You do rides like this so you can experience this kind of beauty.

I remember going up the backside of Hogback and saying out loud – “this climb will never fucking end.” For some reason that struck me as funny because it literally ended one minute later.

At Eric’s urging we had agreed to stay together as much as possible in the dark, both for the shared power of our lights and the strength of numbers. If one of us got to the top of a climb before everyone else, we waited. We talked a lot, about what I couldn’t tell you. It helped pass the time and that makes a big difference.

Eventually Dana whizzed by me and we hit Dickey Ridge and coasted downhill for almost four miles to the end. The Dickey Ridge descent is one of the great payoffs in local cycling. You beat your brains out climbing and climbing and climbing but you get 6-8 solid minutes of 30-40+ mph descending to finish. Another reason Skyline is the best.

We made it back to the car just before 11:00pm, about sixteen and half hours after we started. We rode 208 miles and climbed 20K feet and I burned 8,000 calories.

A proper bike ride.

5 thoughts on “Skyline Double

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