Fall Into Fun: Fall Festivals Near Winchester
There’s nothing like fall in Winchester—cool mornings, colorful leaves, and plenty of chances to get outside. One of the best parts of the season is the variety of festivals happening in and around town. From pumpkin patches and corn mazes to live music and apple cider, there’s truly something for everyone.
Whether you’re new to the area or a long-time local, these events are a great way to enjoy the season with friends, family, or neighbors. In this guide, we’ll highlight some of the top fall festivals that bring our community together.
Fall Festivals Near Winchester:
- Celebración of Winchester
- Shenandoah Valley Apple Harvest Festival
- Great Country Farms: Pumpkin Harvest & Corn Maze
- West Oaks Farm: Fall Harvest & Apple Harvest Festivals
- Wayside Farm Fun: Corn Maze & Fall Activities
- Marker‑Miller Orchards: Apple & Pumpkin Festivals
- Bear Chase Brewing: Beer & Wine Festival
- Tips for Attending Fall Festivals
Celebracion of Winchester (September)
To kick off the season, Celebración of Winchester is all about community. You’ll find live Latin music, dance performances, crafts, and authentic food that reflect the city’s diverse culture. As a result, it’s one of the most festive and family-friendly ways to welcome autumn.
Shenandoah Valley Apple Harvest Festival (September)
If you love apples, this is the one to mark on your calendar. Held at the Frederick County Fairgrounds, the Apple Harvest Festival features food vendors, live music, pony rides, a car show, and of course—plenty of apple pie. In fact, it’s such a beloved tradition that locals are known to return year after year.
Great Country Farms Fall Festivals (September-November)
Great Country Farms in Bluemont is a favorite spot for families, and their fall festivals are packed with activities. Throughout the season, you’ll find something new to enjoy:
- Apple Gala & Cider Fest (September weekends): Try fresh-pressed cider, grab a cider donut, and stroll through the corn maze.
- Family Flashlight Nights (September evenings): Bring a flashlight and take on the corn maze after dark. Marshmallows and bonfires make it extra cozy.
- Fall Pumpkin Harvest Festival (October): Pick pumpkins, watch pig races, explore the maze, and catch P-Rex, the pumpkin-eating dinosaur, in action.
- Pumpkin Chunkin’ (Early November): End the season with a bang—literally—by launching leftover pumpkins through the air.
No matter when you visit, Great Country Farms delivers festive fun for all ages.
West Oaks Farm: Apple & Fall Harvest Festivals (October)
Just a short drive from town, West Oaks Farm Market hosts two popular fall events. Both are wonderful ways to enjoy the fresh flavors and scenery of the season:
- Apple Harvest Festival: Enjoy apple picking, hayrides, live music, and carnival-style games. Free to attend, it’s a great day trip with friends or kids.
- Fall Harvest Festival: Later in the month, you’ll find even more seasonal fun—produce, food trucks, kids’ games, and local entertainment all in one place.
Wayside Farm Fun: Corn Maze & Family Attractions (September–November)
Looking for a spot where the kids can run wild? Wayside Farm Fun in Berryville has it all. From farm animals to slides, there’s an activity for every energy level:
- Corn Maze & Pumpkin Patch: A giant themed maze and an 8-acre pumpkin patch.
- Pig Races & Petting Zoo: Weekend races and friendly farm animals like goats, calves, and donkeys.
- Farm Attractions: Mega slides, Hay Mountain, a jumping pillow, duck races, and more.
- Food & Market: Burgers, kettle corn, and sweets, plus a farm shop full of local goodies.
Altogether, this spot makes for a day of laughter and fresh-air adventure.
Marker-Miller Orchards: Apple & Pumpkin Celebrations (October)
A true Winchester favorite, Marker-Miller Orchards is known for its welcoming atmosphere and fresh produce. To boot, their fall festivals feature apple picking, hayrides, homemade treats, and local crafts. It’s a relaxed, family-friendly outing that’s close to home.
Bear Chase Brewing: Beer & Wine Festival (October)
If you’re looking for something more adult-oriented, Bear Chase Brewing in Bluemont is a great choice. Their fall Beer & Wine Festival features craft tastings, live music, food trucks, and stunning Blue Ridge views. Consequently, it’s the perfect way to enjoy fall flavors in a scenic setting.
Tips for Attending Fall Festivals in Winchester
Before you head out, keep these tips in mind to make your festival days even better:
Pack a bag: A reusable tote is perfect for apples, crafts, or baked goods.
Dress in layers: Mornings can be cool, afternoons warmer.
Wear comfy shoes: Corn mazes and hayrides mean lots of walking.
Bring cash: Some vendors don’t accept cards.
Go early: You’ll avoid crowds and have the best pick of pumpkins.
Take photos: Golden hour makes the prettiest fall pictures.
By planning ahead, you can make the most of every festival this season.
Celebrating Fall in Winchester
Fall in Winchester is full of opportunities to get outside and enjoy the season. Whether you’re picking apples, sipping cider, or cheering on pig races, these festivals are a great way to make memories close to home. Above all, they remind us why autumn is one of the most celebrated times of year in our community.
Looking for even more local tips and happenings? Check out what’s going on around downtown and see why living at The Local Apartments in Winchester, VA, keeps you close to the action.