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šŸŽ‰ Festival Season at Wildside Winery: Magic in Every Moment šŸŽ‰

Sep 8, 2025
3 min read

As the leaves turn and the air takes on that crisp autumn feel, Wildside Winery comes alive with the spirit of celebration. For 21 years, our family-owned and operated winery has welcomed friends, neighbors, and travelers alike to sip, shop, and share in the joy of Kentucky’s harvest season. šŸ’œšŸ‡


This year’s fall festival lineup is packed with music, magic, and community — and you’re invited to be part of it.


šŸŽˆ Up, Up, and Away! Balloon Festival

šŸ“… Saturday, September 13, 2025

ā° Hot Air Balloon Rides: 6:30 PM (weather permitting)

šŸ’° $20 per person | Cash Only | First come, first served


Imagine hot air balloons rising into the sunset while music, laughter, and the smell of great food fill the vineyard. šŸŽ¶šŸ”


šŸŽ¶ Live Music: Matt Castle (2–5 PM) & Hi-5 (6–9 PM)

šŸ›ļø Handcrafted goods, artisan booths, and specialty boutiques

šŸ” Food trucks serving up seasonal favorites

šŸ· Wildside wines and slushees to enjoy all evening

šŸ“ Wildside Winery, Versailles, KY

🚫 Balloon rides are weather-dependent; no reservations accepted.



šŸ‚ Harvest Festival

šŸ“… Saturday, October 4 (12–7 PM) & Sunday, October 5 (12–5 PM)

Celebrate the bounty of the season with two days of music, markets, and community spirit! šŸŒ¾šŸŽØ


šŸŽ¶ Live Music Lineup:

Saturday: John McHugh (1–4 PM) & Trippin Roots (4–7 PM)

Sunday: Ben Lacy & Corey Cross (1–4 PM)


šŸ›ļø Shop handcrafted art, jewelry, and farm-fresh goods from local makers

šŸ” Food trucks with both savory and sweet seasonal favorites

šŸ· Sip Wildside’s seasonal wines while enjoying the beauty of the vineyard


Admission & parking are FREE — perfect for a fall family outing!





šŸŽƒ Pumpkin Festival

šŸ“… Saturday, October 11 (12–7 PM) & Sunday, October 12 (12–5 PM)


Fall’s favorite flavors and colors come alive at the Pumpkin Festival! šŸ

šŸŽƒ Wild Woman Axe Throwing — Saturday, Oct 11:Ā channel your fierce side with a supervised, festival-style axe-throwing experience in partnership with the Pumpkin Festival

šŸŽƒ Pumpkin-Spiced Wine

🌸 Mums for sale to brighten your porch

šŸ›ļø Local vendors, handcrafts, artists, and boutique finds

šŸŽ¶ Live music lineup (TBA)

šŸŽƒ Locally grown pumpkins to take home for decorating or baking

Admission & parking are FREE — celebrate autumn your way!



šŸ§™ā€ā™€ļø Witches & Wine Festival

šŸ“… Saturday, October 25 (12–7 PM) & Sunday, October 26 (12–5 PM)


Step into the magic — this isn’t just a festival, it’s a gathering of wild folks, magic-makers, and wine lovers. šŸŒ™āœØ


šŸŽØ Arts & crafts market featuring handmade creations

šŸ” Food vendors with seasonal favorites

šŸ”® Metaphysical market & astrology sessions

šŸ“š Magical books and spellbinding reads

🐺 Selfies with Wolves (Wolf Run Refuge)

šŸŖ“ Axe Throwing & Costume Contests with prizes

šŸ¹ Witches Brew Slushee, our signature festival potion


šŸŽ¶ Live Music Lineup:

Saturday: Elvis Cocktail (1–4 PM) & Blacktop Rodeo (4–7 PM)

Sunday: Nicola Cassetta & Jake Vanover (12–2 PM) & Five Below Band (2–5 PM)

Admission & parking are FREE — bring your coven and celebrate in style!



Why We Do This ā¤ļø


At Wildside, our festivals are more than events — they are the heartbeat of our community. We’ve been growing, creating, and celebrating here in Versailles for over two decades, and every festival is a chance to bring people together. From Wild Women gathering in circle to families sipping cider under the sunset sky, these are the moments that remind us why we’re here: to create magic, share wine, and nurture connection.


So mark your calendars, tag your crew, and join us this fall. Because at Wildside, the season isn’t just harvest time — it’s festival time. šŸ‡āœØ


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About Wildside Winery
Locally owned and wildly loved, Wildside Winery is a Kentucky destination for wine, community, and creativity. With more than 40 handcrafted wines, year-round festivals, and Wild Woman gatherings, we celebrate living boldly and sipping beautifully.

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Vendor Information

Visit Us
5500 Troy Pike, Versailles, KY
Mon–Sat 12–7 | Sun 12–5
(859) 879-3982
Family & dog-friendly • Free parking

​Outside food & drink not permitted

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