04/05/2026
Our attempt at biking Skyline Drive across Shenandoah National Park. Theme of the week…HILLS! We didn’t quite make the entire 150 miles but we did cover 115 miles and tons and TONS of elevation. Biking day one was by far the most difficult with 15 notable climbs. Not sure why we thought ending the day with a straight uphill hike was a good idea, but the legs were 100% shot by sundown. Thank goodness the yurt we rented had a hot tub. More research was needed on the exact access to the yurt as a hike up a hill, down an illegal fire road, with a bike, was the only direct route back to Skyline Drive. Biking day two was much better. Overall very few cars (and very few bathrooms), one beautiful overlook after another and our sag wagon driver had an easy time following us. The third night we stayed in Charlottesville and found a fun speakeasy and very good seafood spot. For the final biking day we headed from Charlottesville towards Richmond on some beautiful roads and past some gorgeous wineries. Sadly the only winery open on Friday afternoon was the worst wine I have ever tasted. The owners were so sweet (appropriately so) and kept bringing us HUGE tastings of one sweet concoction after another. We needed to find very creative ways to dispose of it. Our final lading spot as Richmond and we took a few days to take in the history and some great restaurants. The days were long so the card playing was short and Jen dominated the game! Happy to share the itinerary, cycling maps, accommodations and other tips for those interested in this bucket list ride!