The Perfect Fall Road Trip in Virginia!

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.  

1. Start the trip out right with coffee from Milli Coffee Roasters

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 we want for our espresso drinks.” The bottom line: their coffee is delicious.

2. Feel your hair blow in the wind as you cruise down Skyline Drive

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. 

3. Grab lunch at Element

You’ll get off Skyline Drive around Front Royal, Virginia, 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.

4. Hike the Appalachian Trail—well, a portion of it

The Appalachian Trail stretches over 2,000 miles end-to-end, so we 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.

5. Pick apples at Stribling Orchard

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. 

6. Hop in the car and head to the haunted Exchange Hotel

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.

7. Visit the capitol and get a few drinks at Kindred Spirit Brewing

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.

8. Get to know other wayward travelers at the HI Richmond Hostel

Stay in the city in style at the HI Richmond Hostel. The hostel is in a beautifully restored, charming historic building right in the center of the action. The interior is rustic and modern. You can choose between staying in an all-female dorm, all-male dorm, co-ed dorm, or spring for a two-person private room. But part of the fun in staying at a hostel is meeting new people, so we suggest you take advantage of the cheaper rates and make a few friends.

9. Take a walk to Perly’s for breakfast

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.” 

Always a definite yes. #fishboard #perlys #rvadine

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10. Take in the James River and the city in Libby Hill Park

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. 

It's been almost 4 years since my guy and I sat on this bench, my arm through his, me in his jacket and him being calm and cool like he always was...like he still is. It was dark and the air was cool. It was late fall and it was our first "date." We didn't do much other than sit on this bench, overlooking the #richmond skyline and talk. But it was so comfortable and simple and good. There was something about him I was drawn to...maybe his quiet confidence or the way he knew all the right things to say, which I still kid him about because I thought he was just trying to use a smooth pick up line or two. Whatever it was, I liked it. And he was different. But more than that, he made ME different. I stopped looking around. I stopped wondering if where I was was good enough. I became content with things that I never could have thought I'd be content with. It was like My heart settled down into him and yet he ignited something inside me at the same time. So in honor of bf day (apparently this is a thing and I almost missed it), a big shout out to the man who makes me feel beautiful at my worst, lets me know I'm enough just the way I am, and who makes my heart still skip a beat when he's around. 💕 . . . #truelove #rva #hometownromance #libbyhill #libbyhillpark #richmond #skyline #bf #fall

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Virginia Search
Best Things To Do Near You
Best Things To Do Near You
Oct
16

Apple Harvest Festival

9:00 AM
Drumheller's Orchard Lovingston, VA
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Oct
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Richlands Dairy Fall Festival

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Annual Fall Festival

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Marcus Johnson

8:00 PM
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Apple Harvest Festival

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Drumheller's Orchard Lovingston, VA
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Oct
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Richlands Dairy Fall Festival

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Annual Fall Festival

11:00 AM
Coyote Hole Ciderworks Mineral, VA
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Oct
17

CMSCVA: American Romantics

4:00 PM
Trinity Lutheran Church Richmond, VA
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