Celebrate the Harvest Season at Winchester VA Fall Festivals

A teen boy checks his watch while walking through thick woods at sunset winchester va fall festivals

Looking for a way to ring in the harvest season this year? Look no further than these awesome Winchester, VA fall festivals! Each of these festivals offers a unique take on celebrating everything autumn has to offer. Check it out!

Kick Off The Season Fun With These Winchester, VA Fall Festivals

Old Town Winchester Oktoberfest 2023

Oktoberfests are Old World festivals deeply rooted in German culture that celebrate a bountiful harvest, gathering as a community, and, of course, great beer! Old Town Winchester’s Oktoberfest exemplifies all of the goodness of a classic Oktoberfest celebration. Featuring local and widespread Virginia breweries, guests can enjoy delicious beer while taking in live entertainment, delicious food, and a very festive atmosphere. Plus, all proceeds go to supporting literacy in the community – what’s not to love about that?! You can stroll Old Town Pedestrian Mall for shopping and dining as you sample beer. Indulge in some Crim’s Concessions Kettle Corn, enjoy the Shenandoah University Band, and capture fond memories in a photo booth. It’s a celebration that sells out quickly, so be sure to get your tickets sooner rather than later!

A teen boy in a blue jacket stands with arms crossed in the woods winchester va fall festivals

Richards FruitMarket

The Richards Family has been selling fruit like apples and peaches to their community since 1953. Today, their legacy lives on in the next generation of Richards farmers. Their Fruit Market is open year-round and sells a variety of seasonal produce, baked goods, meats, eggs, and even Virginia wine. In the fall, their Apple Festival brings a crowd of visitors to celebrate the harvest season – and it’s free admission! Enjoy live music, farm food including their own burgers and farm-to-crust pizza, wine and craft beers, and, of course, lots of apples and apple products! Kids will love exploring the petting zoo, playing lawn games like cornhole, and getting a taste of life on the farm. 

Full Moon Night: Harvest Moon

Fall isn’t just about pumpkins, apples, and flannel shirts; the Harvest Moon is also to be celebrated. The Harvest Moon is the full moon closest to the autumnal equinox, typically at the end of September every year. Known for its unusual brightness, it’s been called the Harvest Moon because its heightened illumination was helpful to farmers and harvesters, who could work late into the night beneath the glow of the moon. It’s also become quite a cultural phenomenon and has been an integral reference in songs, poetry, and other folklore. The Full Moon Night: Harvest Moon event is a celebration where people can gather to symbolically and spiritually acknowledge the beginning of a new phase. Enjoy full moon activities and guided meditations as you “harvest” your own growth and everything you’ve been working towards in the past months. Celebrate the Harvest Moon and yourself! 

A teen boy in a blue jacket runs a hand through his hair at sunset in thick woods

Festival of Leaves

The Festival of Leaves in Historic Downtown Front Royal is a huge celebration of the fall season! You can wander through the booths of over a hundred arts and crafts vendors. Searching for the perfect treasure you didn’t even know you needed! Enjoy three stages of live music, a beer garden, delicious food vendors, and so much more. Kids will love the bounce houses, and families will appreciate taking advantage of all of the downtown shops, restaurants, and historic attractions. It’s the ideal way to gather, celebrate the harvest season, and indulge in tasty treats as you shop!

Winchester VA Fall Festivals

Make sure you squeeze one of these Winchester, VA fall festivals into your schedule – you’ll be so glad you did! From the delicious food and drinks to the family-friendly activities, the spirit of the season will be alive and well at each of these awesome events. 

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