As the temperatures drop and the leaves start turning fiery shades of red, orange, and gold, the Shenandoah Valley becomes a true autumn paradise. From farm festivals to arts & crafts fairs, there’s something for everyone. If you’re planning a fall outing this year, here are the must-do fall festivals in and around the Valley, including Charlottesville and Waynesboro.

🎉 Top Fall Festivals You Won’t Want to Miss

🍂 Massanutten Resort Fall Festival
📅 Saturday, October 11, 2025
📍 Massanutten Resort
Why go: Chairlift rides with mountain views, live music, pumpkin painting, and a beer & wine garden. Fun for the whole family!
🔗 Massanutten Fall Festival

🍎 Shenandoah Autumnfest (Woodstock, VA)
📅 Early October (check dates annually)
📍 Shenandoah County Fairgrounds
Why go: Crafts, local food, live music, and apple butter-making demos. A classic small-town festival.
🔗 Visit Shenandoah Autumnfest Info

🥧 Shenandoah Valley Apple Harvest Festival (Clear Brook, VA)
📅 Mid-September
📍 Frederick County Fairgrounds
Why go: Apple pie contests, vendors, pony rides, and even a classic car show—fun for all ages.
🔗 Apple Harvest Festival Info

✨ Queen City Mischief & Magic (Staunton, VA)
📅 Late September
📍 Downtown Staunton
Why go: Wizarding-themed fun, live performances, and family-friendly activities. A whimsical fall favorite.
🔗 Queen City Mischief & Magic

🏇 Shenandoah Downs & Autumn Events (Woodstock, VA)
📅 Fall weekends
📍 Shenandoah County
Why go: Harness racing paired with seasonal food, music, and local festivities.
🔗 Shenandoah County Events

🍏 Fall Into Fun Festival (Chiles Peach Orchard, Crozet, VA)
📅 September (check dates annually)
Why go: Pumpkin patch, apple picking, hayrides, kids’ crafts, and live music.
🔗 Fall Into Fun Festival

🌽 Liberty Mill Fall Farm Festival
📅 Late September 2025
Why go: Corn mazes, pumpkin patch, farm playground, local vendors, and seasonal treats.
🔗 Liberty Mill Fall Festival

🍎 Graves Mountain Apple Harvest Festival
📅 First three weekends in October
Why go: Bluegrass music, apple picking, pony rides, and hayrides—classic mountain autumn.
🔗 Graves Mountain Apple Festival

🎬 Virginia Film Festival (Charlottesville)
📅 October 22‑26, 2025
Why go: Arts & culture in fall—films, panels, screenings, and indoor festival fun.
🔗 Virginia Film Festival

🎨 Fall Foliage Art Festival
📅 Saturday, October 11, 2025
📍 Downtown Waynesboro
Why go: Artist booths, crafts, food vendors, live music, and a festive stroll.
🔗 Fall Foliage Art Festival

🏃 Fall Foliage 5K & 10K Race
📅 October 11, 2025
📍 Constitution Park, Waynesboro
Why go: Run or walk through beautiful fall scenery—great for fitness enthusiasts and families.
🔗 Fall Foliage 5K & 10K

🍂 Why You Should Visit These Festivals

All the senses: Crunchy leaves, cider, barbecue smells, and live music.
Family-friendly: Crafts, pony rides, and interactive fun for all ages.
Local flavor: Handmade goods, seasonal produce, apple cider donuts, and more.
Perfect weekend road trips: Combine a festival stop with a scenic drive, pumpkin patch, or orchard visit.