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Biking Blog: Does This Go Through? Exploring the Roads of the Shenandoah Valley

There was a time when I hated riding my bike.

Strange for a professional cyclist, right? Couldn’t stand it. At that time, I absolutely loved racing, but riding for fun was not something I was interested in. Training was only a means to an end.

After a winter of very poor training I gained more than 10 pounds and had trouble finishing races. Shortly after the dismal season came to a close, I moved to Harrisonburg, VA to begin my college education. I quickly discovered that Harrisonburg, in the heart of the Shenandoah Valley, had deep cycling roots.

In my first week in Rocktown (Harrisonburg’s original name) I discovered how to love riding.

Without knowing any of the local routes or the safest ways out of town, simply figuring out the roads surrounding Harrisonburg was enough to wet my appetite. I wonder where that goes. Does this go through? How do I get there? More often than not, I never answered those questions. I was still a little afraid of exploring the roads.

So I enlisted the help of an acquaintance I had met on the racing circuit who lived in town. Andy McKeegan, already a veteran route builder and mapping extraordinaire, immediately took me not on training rides but adventures. Five or six hours in the mountains, over dirt roads, through creek crossings, and through the valleys. Half of the time he wasn’t sure if the road we were on went through or how to get to the next one, but that was half of the fun!

As we would continue to explore and get lost, we also nick named regions; Narnia (there is only one way in and you will exit one hour later completely confused, but three actual hours have passed), Middle Earth (exactly what it sounds like), The Swiss Alps, and more.

On these routes I shed the weight I had gained, actually looked forward to riding, and made a great friend. Andy and I would dream about racing professionally, encourage each other in endeavors on and off the bike and keep each other honest with the training. We’d meet at 10 – that’s a lie, ‘Meet at 10’ really meant 10:40 – and find new roads and routes, often coming back nearly frostbitten and in the dark.

My wife and I have since moved, just one valley away, and I don’t often get to ride the routes that taught me to love cycling. With Strava, Ride With GPS, and Garmin Connect, it’s a lot easier to share these routes than in the past. Below are a few links to a few of these digital que sheets – my favorite routes. Please enjoy them, stay safe, and never stop exploring!

There are many cyclists before and after me who have had the pleasure of riding in the Shenandoah Valley, and who have all discovered and created their own routes, or added twists to already popular loops. And though new riders will come upon roads many times traversed already, they will will still wonder ‘Does this go through?’ And the answer will continue to delight.

Connor Bell, U23 US National team rider climbs a dirt road. From my Instagram @curtiswinsor
Connor Bell, U23 US National team rider climbs a dirt road. From my Instagram @curtiswinsor

Recommended Routes leaving from Rocktown Bicycles in Harrisonburg, VA.

Supine Lick Adventure – 90 miles, lots of dirt, plenty of short punchy climbs.

Cub Run PLUS – Two challenging rides, combined into one 90 mile climbers loop.

Crooked Run Death March – Long steady stretches to and from Crooked Run, a steep dirt climb to a cell phone tower.

Guaranteed to Flat – This route features a seldom ridden fire road in West Virginia connecting two of the Reddsih Knob climbs. If you don’t flat, you will certainly damage your rims. Worth it.

One Way – Every March, the town of Montery hosts a maple festival. What better way to prepare to prepare for glutenous maple-everything eating, than a climbing -heavy bike ride?

No Quiche Loop – With 116 miles and 12,000 feet of climbing this route is a bear.

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