- Lexington, KY
- Face Painter / Outdoor Party Entertainment
- 18 miles from Winchester
- Starts at $85 per hour
Melissa C. said
“Exactly what we needed! Arrived on time, great with kids. Will book again! ”
The 11 Best Outdoor Party Entertainers for hire in Winchester, KY
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164 Outdoor Party Entertainers serving Winchester, KY
- Lexington, KY
- Face Painter / Outdoor Party Entertainment
- 18 miles from Winchester
- Starts at $100
Todd P. said
“Kids loved it! Thank you so 6! ”
- Lexington, KY
- Balloon Twister / Outdoor Party Entertainment
- 18 miles from Winchester
- Contact for pricing
Lauren B. said
“She was wonderful! Highly recommend! ”
- Lexington, KY
- Stilt Walker / Outdoor Party Entertainment
- 18 miles from Winchester
- Contact for pricing
Michael T. said
“We hired Hannah Kay, to come to our event. She was a great addition.
Arrived before scheduled, performed and stayed longer than scheduled.
We recommend her. ”
- Georgetown, KY
- Balloon Twister / Outdoor Party Entertainment
- 26 miles from Winchester
- Starts at $100 per hour
Shelley said
“Mandy showed up early to set up. The children loved her balloons. We had more kids than expected and she handled it with ease. Will definitely hire her again! ”
- Frenchburg, KY
- Face Painter / Outdoor Party Entertainment
- 30 miles from Winchester
- Starts at $100
Kristen R. said
“Great addition to the party! They were great organizing the kids and both kids and adults loved the glitter tattoos! Lots of patterns and colors! Would 100% recommend!!! ”
- Lexington, KY
- Mobile Game Activities / Outdoor Party Entertainment
- 18 miles from Winchester
- Contact for pricing
The Rec Shuttle LLC, is a mobile recreation company. We offer a variety of event set ups and rentals. We accommodate functions such as field-days, tailgating...
- Nicholasville, KY
- Party Inflatables / Outdoor Party Entertainment
- 23 miles from Winchester
- Contact for pricing
Welcome! Thank you for visiting and for your interest in our exciting line of inflatable attraction rentals from U Bounce Inc. Here you'll find Lexington's best...
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About booking Outdoor Party Entertainment in Winchester, KY
Outdoor parties are all about enjoying fun in the sun and creating an atmosphere guests won’t forget. The right entertainment sets the stage, whether that means a live band filling the air with music, a DJ keeping the energy high, or a magician amazing guests with close-up tricks. From stilt walkers and petting zoos to face painters and balloon twisters, professional entertainment brings the spark that transforms any backyard celebration, kids party, or festival into an unforgettable experience.
The cost of hiring outdoor party entertainers in Winchester, Kentucky will vary depending on the type of act, their experience, and the length of the performance. For example, a strolling juggler for a few hours will cost less than a full band or stage show. Contact the local entertainers above to discuss your event details and receive a customized quote.
As you browse Winchester outdoor party entertainers, check out their profiles to learn about their services, browse photos, and watch promotional videos. Then, read over reviews from past clients to see how they’ve entertained at similar events. When requesting a quote, include key details such as your event location, audience size, performance space, and overall vibe to get the most accurate pricing.
Once you find the entertainer you want to hire, finalize the booking on GigSalad. Our full-service platform makes it easy to book outdoor party entertainment. You can message the performers, confirm the details of your agreement, and make a secure payment all in one place. Every GigSalad event is covered by our Worry-Free Guarantee, so you can rest easy knowing we’ve got your back. Just sit back and enjoy your party!
Outdoor Party Entertainment serving the Winchester, KY area
These Outdoor Party Entertainment serve the wider Winchester and Clark county area and travel to North Middletown, River, Mount Sterling, Judy, Paris, Clay City, Waco, Richmond, Lexington, Jeffersonville, Eastern, Sharpsburg, Stanton, Winston, and Moorefield.