🍂 10 Best Fall Side Trips from Richmond, Virginia

Virginia is one of the best states for a Fall Road Trip - with mountains, wineries, small towns, and so much history just a short drive away. So grab your flannel and a cozy latte, here are 10 amazing fall side trips from Richmond, VA that’ll make you fall even more in love with this state. 🍁

1. Shenandoah National Park

🚗 2 hours from Richmond

Shenandoah is Virginia’s ultimate fall destination, with the Blue Ridge Mountains glowing in shades of gold and crimson. Cruise along Skyline Drive, hike to Dark Hollow Falls (pictured) or Stony Man, and pack a picnic to enjoy among the views.

Pro tip: Here is my Perfect 1-Day Itinerary at Shenandoah National Park and the Best Fall Things to Do in Shenandoah blogs.

2. Albemarle County & Charlottesville

🚗 1 hour from Richmond

Home to Thomas Jefferson’s Monticello, rolling vineyards, and the charming Downtown Mall, Charlottesville has all the fall vibes. Wander the Carter Mountain Orchard for apple cider donuts (and that panoramic view), stop by Chiles Peach Orchard for some Pumpkin picking or grab a bit at the 1784 Michie Tavern.

Pro tip: Here is my Perfect 1-Day Itinerary in Albemarle County for more Fall things to do in the area.

3. Jamestown

🚗 1 hour from Richmond

Where American history began! Explore Historic Jamestowne and Jamestown Settlement surrounded by fiery fall foliage. Combine it with a drive on the Colonial Parkway, one of the most scenic drives in Virginia, especially this time of year.

Pro tip: Here is my Complete Guide to the Historic Triangle with tons of things to do and see.

4. Yorktown

🚗 1 hour 15 minutes from Richmond

Yorktown offers gorgeous riverside views and Revolutionary War history with small-town charm. Stroll the Yorktown Riverwalk, pop into local shops, or check out their fall festivals. Bonus: The Yorktown Battlefield is stunning with fall colors!

Pro tip: Here is my Perfect 1-Day Itinerary to Yorktown, where you can get your whole day planned out for ultimate Fall vibes.

5. Colonial Williamsburg

🚗 1 hour from Richmond

Stepping into Colonial Williamsburg in fall feels like walking through time with crunching leaves underfoot and flickering lanterns lighting the cobblestone streets. Tour the historic homes, watch a blacksmith at work, and end your day with a cozy meal. This is just the best!

Pro tip: Colonial Williamsburg has a lot going on and can be confusing, so make sure to read my guide on the Best 10 Tips for your Trip to Colonial Williamsburg.

6. Blue Ridge Mountains

🚗 2 hours from Richmond

If you’re chasing the iconic Virginia fall foliage, the Blue Ridge Mountains always deliver. The scenic drives here (like the Blue Ridge Parkway) are unreal in October. Stop for overlooks, hiking trails, and maybe a weekend cabin stay. Perfect for a romantic fall getaway or cozy solo trip.

Pro tip: Here is my Perfect 2-Day Itinerary to the Blue Ridge Mountains with tons of things to do and see in the Fall.

7. Alexandria

🚗 2 hours 15 minutes from Richmond

Alexandria is the definition of cozy fall charm. Picture cobblestone streets, historic brick townhouses, and twinkle lights reflecting on the Potomac. Spend the day exploring Old Town or shop along King Street. Plus it's close to D.C. if you care to wander over there!

Pro tip: Watch my 5 Best Things to Do in Alexandria Vlog, which is filmed in October with tons of things to do and see in the Fall.

8. Harrisonburg

🚗 2 hours from Richmond

A hidden gem in the Shenandoah Valley! Harrisonburg has an artsy downtown, cool murals, and easy access to mountain trails. Do a cider tasting at Sage Bird Ciderworks, grab a latte at Broad Porch Coffee, or wander the campus at JMU for Fall foliage.

Pro tip: Watch my 5 Surprising Things to Do in Harrisonburg vlog where Lukas and I visit Harrisonburg for the first time exploring all the cozy things to do and see.

9. Staunton

🚗 2 hours from Richmond

One of Virginia’s prettiest small towns! Staunton has a walkable downtown packed with antique stores, charming cafés, and historic architecture. Don’t miss the American Shakespeare Center or the Woodrow Wilson Presidential Library. Plus, the fall colors surrounding the town? Unreal.

Pro tip: Watch the vlog where I take my parents to Staunton and the surrounding areas for some fun things to do in Fall.

10. Middleburg

🚗 2 hours 15 minutes from Richmond

Middleburg is a serious vibe - rolling hills, horse farms, and chic countryside inns. Visit Mt Defiance Distillery and Cidery, explore downtown boutiques, and grab lunch at Red Fox Inn, one of the oldest taverns in America. It’s Virginia luxury meets small-town charm.

Pro tip: Watch the video of our stay in this area, where we cover Everything to See & Do near Middleburg.

🍁 Final Thoughts

Whether you’re chasing leaf-peeping perfection in the mountains or cozying up in a historic town, these day and weekend trips from Richmond show off Virginia’s best fall magic. So grab your favorite Fall-loving friend and let’s make this fall unforgettable!

I hope you found this list helpful! There are more blogs on my website about Richmond travel tips.

You can also follow me on YouTube for my lifestyle vlogs & travel videos in Richmond or Instagram for daily updates.

If you have any questions or comments, feel free to DM me on Instagram any time.

💚 Lauren