Last Updated on: 19th September 2021, 11:40 pm
Skyline Drive is a stunning section of Shenandoah National Park in the middle of Virginia, easily accessible for those driving from Charlottesville to Washington, DC. The drive overlooks the Blue Ridge Mountains and stretches for a little over a hundred miles. This length makes it a short enough to enjoy in the middle of a longer driving day, but long enough that it can be it’s own activity.
My first introduction to Skyline Drive was in 2009, on a friends’ road trip through Virginia Wine Country. At twenty-five, this was right about the time we were all starting to ditch keg parties for events where people referenced their drinks with words like oak and vintage. I was shocked to learn a six-dollar bottle of Yellow Tail even had a vintage. I think we thought we were becoming adults. Seven years later I’m not sure if I’ll ever be one.
Shenandoah was the perfect way to end that weekend and drive back to Washington, DC (where I caught I Chinatown bus back to Philadelphia, the least grown-up form of transportation invented by man. Remind me sometime to tell the story of my last Chinatown Bus ride, circa 2011, and why I promised myself never again). Since then, I’ve gone back twice, most recently time was in January, while I was on my crazy, scatter-shot USA extravaganza.
Here are photographs from my three drives, in three different seasons: winter, summer, and autumn. Spring, I’ll have to come back for you.
My Favorite Travel Booking Sites for 2023
These are my favorite companies that I use on my own travels.
Protect Your Trip via Safety Wing
Find the best city tours, day tours, bus tours, & skip-the-line tickets on GetYourGuide and Viator.
Find the best deals on hotels & vacation rentals on Booking.com.
For English-speaking private airport transfers, book through Welcome Pickups.
For road trips and independent travel, rent a car through Discover Cars.
Find information and cruise reviews on Cruise Critic.
For packing and travel essentials order via Amazon.
Book an affordable family or romantic photography session on your trip through Flytographer (Use the code HISTORYFANGIRL for 10% off your first photoshoot).
For travel guidebooks to have with you during your trip, I always pick one or two from Rick Steves and Lonely Planet.
Skyline Drive in Winter








Skyline Drive in Summer





Skyline Drive in Autumn





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