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159 Family Entertainers serving Middleton, WI

Featured

Jonathan Elkins - Magician

5.0 (4)
6 Verified bookings

  • Middleton, WI
  • Magician / Family Entertainment
  • Starts at $350

Judy J. said “Jonathan kept our Cub scouts and their siblings very entertained at our recent meeting. The little kid giggles said it all. I would definitely hire him again.”

Caricatures by Bernie

5.0 (32)
Top Performer
57 Verified bookings

  • Madison, WI
  • Caricaturist / Family Entertainment
  • 5 miles from Middleton
  • $150 – $200 per hour

Lisa L. M. said “We loved having Bernie, it was a great time. If anything plan for a longer time!”

Classic Creations

5.0 (3)
7 Verified bookings

  • Madison, WI
  • Face Painter / Family Entertainment
  • 5 miles from Middleton
  • Contact for pricing

Maria A. said “Great attitude Quick response Beautiful art”

Twist N Shout Madison

4.90 (19)
30 Verified bookings

  • Madison, WI
  • Balloon Twister / Family Entertainment
  • 5 miles from Middleton
  • Starts at $44

Addie P. said “Joe was fantastic at our company picnic. He brought joy to our guests, and expertly made awesome ballon sculptures. I would recommend him for any ballon needs! ”

Premier Face Painting

5.0 (5)
1 Verified booking

  • Madison, WI
  • Face Painter / Family Entertainment
  • 5 miles from Middleton
  • Starts at $150

Danielle D. said “Wonderful job! Arrived on time, was super efficient and quick and the kids loved it. Would definitely recommend!”

James the Magician

5.0 (18)
25 Verified bookings

  • Madison, WI
  • Magician / Family Entertainment
  • 5 miles from Middleton
  • $300 – $5,000 per event

Dylan R. said “James performed for 90 minutes during the cocktail hour of my wedding. He focused on close up magic. James blew everyone away! His tricks were so good and he was very personable and professional....”

Swanky Social Photobooth

2 Verified bookings

  • Cross Plains, WI
  • Photo Booths / Family Entertainment
  • 8 miles from Middleton
  • Starts at $595

Since 2013, we been capturing the fun and adding sophistication to special events. We're all about elevating your occasion, bringing together the beautiful...

InkyDinkyDoo FacePainting

5.0 (1)
1 Verified booking

  • Sun Prairie, WI
  • Face Painter / Family Entertainment
  • 16 miles from Middleton
  • $100 per hour

Dylan H. said “Heather was so great for my party. She was able to bring to life some uniquely specific (the Titanic sinking for example) requests for kids and adults alike! She was a big hit and I had lots of people...”

Patrick's Funny Farm

4.79 (4)
11 Verified bookings

  • Marshall, WI
  • Petting Zoo / Family Entertainment
  • 23 miles from Middleton
  • Starts at $600

Megan L. said “I booked Patrick's Funny Farm for a campus event, and I could not have asked for a better vendor. The outdoor event had to be moved inside due to weather issues, and they worked with us so our...”

Fantasy Faces by Kelly

5.0 (2)
2 Verified bookings

  • Baraboo, WI
  • Face Painter / Family Entertainment
  • 29 miles from Middleton
  • Starts at $150

Jennifer K. said “Kelly came out to paint faces at my 12-year-old son's birthday party in May. Now, most 12-year-old boys probably aren't typically interested in getting their faces painted, but when you can be...”

Ryan Biddle

5.0 (3)
7 Verified bookings

  • Baraboo, WI
  • Caricaturist / Family Entertainment
  • 29 miles from Middleton
  • Contact for pricing

Gina V. H. said “Ryan was awesome. Everyone loved their picture. ”

Caricatures by the Funny Drawing Guy

5.0 (6)
12 Verified bookings

  • Baraboo, WI
  • Caricaturist / Family Entertainment
  • 29 miles from Middleton
  • $200 – $300 per hour

Morgan S. said “Tony was very personable and talented. All of the party attendees loved his work and had a wonderful time!”

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About booking Family Entertainment in Middleton, WI

Family events come to life with entertainment that delivers fun, laughter, and unforgettable memories for every generation. The right performers set the tone, whether it’s a lively musician or DJ getting everyone dancing, or a magician who amazes kids and adults alike. From face painters and balloon twisters to jugglers, clowns, and interactive games, professional entertainers transform birthdays, picnics, reunions, and community gatherings into joyful celebrations.

The cost of hiring family entertainers in Middleton, Wisconsin will vary depending on the type of entertainment, their experience, and the length of the performance. Services like balloon twisting may be cheaper than more involved performances like magic shows. Contact the local acts above to discuss your event and receive a customized quote.

As you explore Middleton family entertainers, check out profiles to learn about their party packages, browse photos, and watch promotional videos. Then, read reviews from past clients to see how they’ve brought the fun to similar events. When requesting a quote, communicate things like your event location, audience size, performance space, and desired atmosphere to get the most accurate pricing.

Once you find the performer you want to hire, finalize the booking on GigSalad. Our full-service platform makes it easy to book family-friendly entertainment. You can message the acts, 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 let the family fun begin!

Family Entertainment serving the Middleton, WI area

These Family Entertainment serve the wider Middleton and Dane county area and travel to Springfield, Madison, Waunakee, Verona, Fitchburg, Cross Plains, Monona, Dane, McFarland, Black Earth, De Forest, DeForest, Oregon, Mount Horeb, Morrisonville, Lodi, Windsor, Cottage Grove, Mazomanie, Sun Prairie, Sauk City, Belleville, Prairie Du Sac, Blue Mounds, Arlington, Brooklyn, Stone, Stoughton, Lake Wisconsin, and Merrimac.