Our bike trip began with a lot of logistics. We drove two cars out to the mountains, leaving one a the southern end of Skyline drive, and driving the second car and bikes to the northern end. The plan was to ride 50 miles–the halfway mark–to Big Meadows Lodge on day 1, and then 55 miles on day 2 to Rockfish Gap where the first car would be waiting. We would then drive back up to the northern end, retrieve car number two and drive home.
It didn’t quite work out that way!
On Saturday we began at a bike shop picking up a few last minute supplies.

From the bike shop we drove southwest from Arlington across the Shenandoah Valley. It was peak fall foliage and gorgeous weather and the drive was exceedingly pleasant! We decided we would make a stop at a winery and the best choice on our route was the Prince Michel Vineyards & Winery. It was clearly a good day for a romantic date at a Virginia winery so Brett and I felt a bit out of place!
I can tell you, however, on an empty stomach that wine makes one silly pretty fast! When we finished our tasting we decided to take a self-guided tour to sober up a bit before getting back on the road. The winery had a lot of beautiful memorabilia, and the tour of the tanks and barrels was interesting. When we left they were setting up outdoors for what was going to be a really perfect wedding!
Next it was time for lunch and we selected a quintessential Virginia BBQ joint that could easily have been featured on the Food Network. It was called the Pig N’ Steak in Madison, VA.
It was about 5 miles down the road from Prince Michel and when we walked in it felt like we’d entered the past! There was an Uncle Remus Flour poster on the wall and country music playing. Everything on the menu looked epic so we asked our waitress if we only had one shot, what should we have? She directed us to the Pulled Pork Sandwich with some of the best baked beans I have ever had. The bbq was spectacular and had the distinct flavor of something that had been slow-cooking all day long.
Now well fed and watered, we headed to Rockfish Gap, the southern end of Skyline Drive. This tiny hamlet is located between Charlottesville and Waynesboro and is the point at which Skyline Drive becomes the Blue Ridge Parkway. At this point what had been a beautiful drive became almost overwhelming in its beauty!

We arrived at Rockfish Gap just a little before sunset. The Afton Inn has a large parking lot and allows people to leave their car overnight. From this elevated piece of ground the view was inspiring!

Saturday night. In hindsight this may not have been the blessing it seemed!
We found a couple fun spots in Winchester including the Picadilly Public House and Brewbakers. This is where my teenage daughter and her friends would simply say, “YOLO!!!” (you only live once) but not only am I not convinced that this is true, it does a person no good when they have an olympic level bike ride ahead of them.
One would think that in my 50+ years I would have learned this lesson before and while I have indeed taken this class many times, I clearly have not learned the lesson!
We got back to our hotel in Winchester at around midnight and settled in for the big bike ride the next day.
In my next post I will detail the ride, the views, and the challenges. There was a lot of each!
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