Fall Festivities in Northern Virginia & the Eastern Panhandle: September & October 2025

1. Bluemont Fair – September 20–21, 2025
Bluemont, VA
The Bluemont Fair is a Loudoun County classic, nestled at the base of the Blue Ridge Mountains. Expect live music, local crafts, delicious food, and a kids’ fair that keeps little ones entertained all day. Don’t forget to stop by the wine garden or hop on a tractor-pulled hayride.

Perfect For: A full day of local flavor, mountain views, and nostalgic small-town fun.

2. Leesburg Airshow – September 27, 2025
Leesburg, VA
One of the most thrilling family events of the fall! Watch pilots show off daring stunts, skydivers float down in style, and vintage planes take center stage. Pack a blanket, grab food from local trucks, and be ready for an action-packed day at Leesburg Executive Airport.

Tip: Bring ear protection for little ones—those jets can roar!

3. Harpers Ferry Oktoberfest – September 28, 2025
Harpers Ferry, WV
Celebrate German tradition in one of the most scenic towns around. Pair bratwursts and giant pretzels with craft beer, live music, and a Blue Ridge Mountain backdrop. The atmosphere is unbeatable, and the food? Even better.

Don’t Miss: The oversized pretzels—soft, salty, and unforgettable.

4. Mountain Heritage Arts & Crafts Festival – October 10–12, 2025
Jefferson County, WV
Shop over 200 artisans while enjoying live bluegrass, regional wines, and classic fair food (funnel cakes included). It’s a one-stop shop for unique holiday gifts or something special for your home.

Bring Home: Handmade jewelry, pottery, or woodwork you won’t find anywhere else.

5. Clifton Day Festival – October 12, 2025
Clifton, VA
For one day, the historic town of Clifton transforms into a vibrant street festival with antiques, art, food, and live music. Pony rides, kid activities, and train rides into town add extra fun.

Pro Tip: Take the VRE train—it’s stress-free and adds to the adventure.

6. Capon Bridge Founders Day Festival – October 18, 2025
Capon Bridge, WV
This small-town celebration brings history, parades, arts and crafts, and live entertainment together for a charming community event. Just across the WV border, it’s a fun day trip with a cozy, neighborly feel.

Best For: History buffs, parade lovers, and anyone craving authentic local charm.

7. The Great Pumpkin Ride – October 25, 2025
Warrenton, VA
Grab your bike and pedal through Fauquier County’s fall scenery. Choose from routes of 11 to 67 miles and enjoy farmland views, small towns, and colorful foliage along the way. The best part? The ride ends with pumpkins, cider, and fall treats.

Bonus: Every mile supports the Fauquier Trails Coalition.