- Wakefield, MA
- Face Painter / Family Entertainment
- 5 miles from Winchester
- Starts at $145
Kathleen said
“Cheryl was very good with the kids, truly the perfect edition to a Halloween event!”
The 105 Best Family Entertainers for hire in Winchester, MA
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241 Family Entertainers serving Winchester, MA
- Allston, MA
- Face Painter / Family Entertainment
- 7 miles from Winchester
- Contact for pricing
Sam S. said
“Paula was great! Incredibly professional and stayed a little late to ensure all the kids got their face painted. 10/10 would recommend and will be booking her again!”
- Boston, MA
- Magician / Family Entertainment
- 8 miles from Winchester
- $500 – $2,000 per event
Peter C. said
“Chandler's magic was amazing. He was also quite entertaining. We hired him for an annual holiday party of about 35 people. Everyone was thoroughly impressed and enthralled. He made the evening a...”
- Boston, MA
- Balloon Twister / Family Entertainment
- 8 miles from Winchester
- $450 – $3,000 per event
Elizabeth T. said
“Fantastic!!! My kids loved the balloons and energy.”
- Boston, MA
- Magician / Family Entertainment
- 8 miles from Winchester
- Contact for pricing
Jeanette B. said
“Matt did table side magic for 150+ seniors for our annual National Asisted Living Week Luncheon this past week and he was phenomenal! Very impressive, got the crowd going between dancing & dinner &...”
- Boston, MA
- Balloon Twister / Family Entertainment
- 8 miles from Winchester
- Contact for pricing
Caroline L. said
“Perfect for our low key backyard party, she was a pleasure to communicate with and to have at our home. She was great with the kids and made an effort to create balloons that went with our themes!...”
- Rockland, MA
- Magician / Family Entertainment
- 25 miles from Winchester
- Starts at $100
Berry X. said
“we had a great time with The Great Scott!”
- Burlington, MA
- Face Painter / Family Entertainment
- 5 miles from Winchester
- Contact for pricing
Joe S. said
“Ione did a great job! This is the second time we've used her ... and we shall use her again!”
- Boston, MA
- Magician / Family Entertainment
- 8 miles from Winchester
- Contact for pricing
Kristina T. said
“Mike put on an awesome show. He was punctual, prepared and very organized. He was engaging with the crowd and was just an absolute pleasure to be around. Everyone was amazed by his talent. Fun was...”
- Boston, MA
- Bubble Entertainment / Family Entertainment
- 8 miles from Winchester
- Starts at $375
Laura P. said
“Cami did a great job with the Bubble Show!!! Very entertaining and kept the kids excited for the next BIG Bubble. The favorite was the Snow!!!”
- Concord, MA
- Face Painter / Family Entertainment
- 11 miles from Winchester
- Contact for pricing
Olga said
“Raddo did a wonderful job. Adults and children enjoyed the face painting experience! ”
- Hyde Park, MA
- Face Painter / Family Entertainment
- 14 miles from Winchester
- Contact for pricing
Alyce said
“Regina provided airbrush tattoos at my daughter's 8 year old birthday party. The art work was great and the kids absolutely loved it. Regina was so professional and great with the kids. This was...”
- Westwood, MA
- Magician / Family Entertainment
- 17 miles from Winchester
- Starts at $400
Christine G. said
“The entire Donnino family was amazingly entertaining. Their performance left our guests in awe! As a family campground, it was the perfect act to book for an evening that was appropriate for all ages....”
Munsey's Magic
- Medford, MA
- Magician / Family Entertainment
- 3 miles from Winchester
- Contact for pricing
L N. said
“I hosted a surprise party for my friends 28th birthday. We had 16 guests. Not only did Jim carefully cooperate with me for the surprise to happen, he was an incredibly thoughtful guest! There was a...”
- Boston, MA
- Photo Booths / Family Entertainment
- 8 miles from Winchester
- Contact for pricing
Marco F. said
“Memento Photo Booth was absolutely incredible! From the initial communication through the end of our event, the team was professional, responsive, organized, and genuinely committed to making the...”
Stephanie Beach Magic
New member- Littleton, MA
- Magician / Family Entertainment
- 20 miles from Winchester
- Starts at $295
I use the art of magic to bring wonder, laughter, and memorable moments to audiences of all ages. From children’s birthday parties to strolling magic at...
- Arlington, MA
- Magician / Family Entertainment
- 3 miles from Winchester
- Starts at $400
Srividya M. said
“Jack made the event so much fun and catered to all ages it was a success!”
- Chelmsford, MA
- Face Painter / Family Entertainment
- 16 miles from Winchester
- Starts at $95 per hour
Roberta A. said
“Sarah is great! My daughter and her friends loved her glitter paintings, and shiny tattoos!
She really made our party!
Highly recommend Sarah for her skills and professionalism.”
- Chelmsford, MA
- Caricaturist / Family Entertainment
- 16 miles from Winchester
- $100 – $150 per hour
Megan R. said
“We had a small “corporate” event of about 60ish people. Dave banged out tons of portraits for my employees and they all loved it! 10/10 recommend Dave and will hire again when needed. Thanks Dave!”
- Boston, MA
- Magician / Family Entertainment
- 8 miles from Winchester
- Contact for pricing
Lorie K. said
“Peter O'Malley is a true magician. He engages the crowd and makes it fun for all. ”
- Lynn, MA
- Face Painter / Family Entertainment
- 10 miles from Winchester
- Starts at $100
Mallory P. said
“I have never seen face painting like this. It was amazing and all the kids loved it. You will be contacted for any future events. Thank you.”
- Salem, MA
- Caricaturist / Family Entertainment
- 13 miles from Winchester
- Starts at $100 per hour
Candice M. said
“Josh was very professional, easy to work with, and created awesome caricatures of our students for our school event!”
- Randolph, MA
- Balloon Twister / Family Entertainment
- 21 miles from Winchester
- Contact for pricing
Erin C. said
“Hire him! He kept kids ages 1-7 entertained with his magic and balloon twisting for the duration of our party. You won’t regret it! Thank you Mr. Twister!! ”
- Allston, MA
- Puppet Show / Family Entertainment
- 7 miles from Winchester
- $250 – $500 per event
Courtney said
“Brenda was very kind and professional planning and performing the Bella Show. The two year-olds were captivated! She really went above and beyond to make it a very special experience for my toddler....”
- Wilmington, MA
- Magician / Family Entertainment
- 7 miles from Winchester
- Starts at $300
Ester D. said
“Really good! Everybody enjoyed the card tricks”
- Boston, MA
- Caricaturist / Family Entertainment
- 8 miles from Winchester
- $150 per hour
Colleen W. said
“Great fast professional and above all FUN ! ”
- Brookline, MA
- Magician / Family Entertainment
- 8 miles from Winchester
- Starts at $400
Rick G. said
“Oliver came to our restaurant and did magic for our guests that were dining and drinking. Everyone had an amazing time and Oliver really brought some fun and excitement to the dining room. We can't...”
- Salem, MA
- Face Painter / Family Entertainment
- 13 miles from Winchester
- Contact for pricing
Jennifer B. said
“I cannot recommend The Funky Brush Face Painting highly enough! From the moment I reached out, Tracy was incredibly responsive, answering every message quickly and making communication effortless....”
- Lowell, MA
- Face Painter / Family Entertainment
- 15 miles from Winchester
- $150 – $175 per hour
Medeiros said
“Kim was great at communicating when and where she would be able to come. She was very excited about painting the faces of the children and adults. Thank you very much.”
- Lowell, MA
- Face Painter / Family Entertainment
- 15 miles from Winchester
- Starts at $300
Hannah B. said
“Ahna was so great! She was really awesome interacting with the kids, and her face painting designs were fabulous.. she's a very talented. She was also easy to communicate with prior to the event,...”
- Natick, MA
- Game Show / Family Entertainment
- 16 miles from Winchester
- Contact for pricing
James M. said
“We hired The Traitors Experience for my daughter’s 11th birthday, and it was a huge hit with all 12 girls! They loved getting into character, searching for clues, and solving the mystery. He was...”
- Stoneham, MA
- Puppet Show / Family Entertainment
- 3 miles from Winchester
- Starts at $250
Anais G. said
“We did not get to see Maggie’s show because she fell sick the day of the performance but she moved heaven and earth to find a replacement at the last minute. Debbie was able to fill in and was...”
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About booking Family Entertainment in Winchester, MA
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 Winchester, Massachusetts 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 Winchester 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 Winchester, MA area
These Family Entertainment serve the wider Winchester and Middlesex county area and travel to West Medford, Woburn, Stoneham, Arlington, Medford, Arlington Heights, Melrose, Malden, Belmont, Lexington, Burlington, Wakefield, Somerville, Waverley, Everett, Reading, North Waltham, Cambridge, Watertown, New Town, Charlestown, Saugus, Chelsea, Allston, Wilmington, Pinehurst, Revere, Hanscom Afb, Nonantum, and Waltham.