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The Perfect Fall Road Trip in Virginia!

va fall road trip

The perfect fall road trip is almost impossible to pin down: Virginia has such rich beauty and history that you simply can’t go wrong anywhere you go. While it may be tempting to read that as an endorsement of aimless travel, we think it’d be better to have a plan. That’s why we’ve come up with the following itinerary that would make anyone a Virginia lover.  


Milli Coffee Roasters, Charlottesville, VA

Get your coffee fix at Milli Coffee Roasters in Charlottesville before heading out on what promises to be a busy weekend road trip. Milli’s has an in-house small batch roaster, which allows them “to create the unique flavor profiles they want for their espresso drinks.” The bottom line: their coffee is delicious.

Driving Skyline Drive at Shenandoah National Park, Luray, VA

From Charlottesville, you won’t have to travel far before getting to your first scenic area. Skyline Drive is world-renowned for its beauty. The drive cuts through the Shenandoah National Park and has a maximum speed limit of 35 miles per hour. Pick any of the 75 overlooks along the way—you can’t go wrong. 

Element, Front Royal, VA

You’ll get off Skyline Drive around Front Royal and from there why not stop in the city for lunch at the elegant Element? Element has delicious and reasonably-priced American fare, with fantastic sandwiches and salads, along with vegetarian options.

Appalachian Trail, Harpers Ferry, WV

The Appalachian Trail stretches over 2,000 miles end-to-end, so you won’t be hiking the entire thing on this road trip. But that doesn’t mean you can’t hike a portion of it! Front Royal has an access point along route 522. Hike for as long as you like, just to say you’ve hiked the Appalachian Trail.

Stribling Orchard, Markham, VA

Now it’s time for a classic fall activity: apple picking! Head to Markham, Virginia, for some great picking at Stribling. At the orchard, you’ll find a variety of apples including Gala, McIntosh, Cortland, Red Delicious, Golden Delicious, Empire, and more. 

The Exchange Hotel, Gordonsville, VA

Got your apples? Good. Now it’s time to hold on to your head. The Exchange Hotel in Gordonsville, Virginia, just under an hour away from Drumheller’s Orchard, is Virginia’s only standing Civil War receiving hospital. Over 70,000 had been treated at the hospital before the end of the Civil War, and over 700 are buried on the grounds. Their ghosts haunt the halls at night.

Kindred Spirit Brewing, Goochland, VA

Up for another short drive? Great! After you’ve checked for ghosts, turn out of Gordonsville and hop on I-64 all the way to Richmond. Don’t stop until you pull in to Kindred Spirit Brewing’s parking. They’ve got over 17 of their own brews on tap with bar food and frequent live entertainment.

Perly's Restaurant & Delicatessen, Richmond, VA

You could take advantage of the free breakfast at the hostel, but when in Rome (or Richmond, in this case), you go to Perly’s. Perly’s is a retro chic Jewish delicatessen with amazing breakfast and brunch options. According to Your Definitive Guide to the Best Brunch Spot in All 50 States, “This is food that would make your bubbie proud.” 

Libby Hill Park, Richmond, VA

End your incredible weekend with a hilltop vista overlooking the James River at Libby Hill Park. The park spans seven acres and is in the Church Hill neighborhood, about a ten-minute drive from Perly’s. If you have time, head to the James River before heading back to see the beautiful changing colors and this hidden oasis in the busy Richmond streets. 

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