- Boston, MA
- Magician / Family Entertainment
- 8 miles from Winchester
- Contact for rates
Sean B. said
“Matt was fantastic, highly reccomend! ”
The 105 Best Family Entertainers for hire in Winchester, MA
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240 Family Entertainers serving Winchester, MA
- Boston, MA
- Magician / Family Entertainment
- 8 miles from Winchester
- $500-$2,000
Lauren N. said
“Days later and the guests from my event are still talking about the magic! Dave was a huge hit and I could not be more pleased with not only the performance aspect of working with him, but also the... ”
- Boston, MA
- Balloon Twister / Family Entertainment
- 8 miles from Winchester
- $450-$3000 depending on travel distance/ style
Elizabeth T. said
“Fantastic!!! My kids loved the balloons and energy. ”
- Boston, MA
- Balloon Twister / Family Entertainment
- 8 miles from Winchester
- $150-200/hr per artist
Kathryn H. said
“Taylor texted me the night before the event to confirm everything. She was punctual and great with the kids. Her face paint was fantastic and the balloons were such a hit! ”
- Boston, MA
- Balloon Twister / Family Entertainment
- 8 miles from Winchester
- Contact for rates
Stephanie D. said
“Balloon Lady Clown provided entertainment for my daughter’s first communion party. She was so accommodating and kind toward all of the adults and children at the party. We booked her for an hour.... ”
- Rockland, MA
- Magician / Family Entertainment
- 25 miles from Winchester
- $100 and up
Curtis B. said
“Scott made it easy to plan the visit. His 15 minute singing telegram show has funny moments. Scott has a really good voice and his Harry Heart costume surprised a teenager birthday party and caused... ”
- Burlington, MA
- Face Painter / Family Entertainment
- 5 miles from Winchester
- Contact for rates
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 rates
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
- Face Painter / Family Entertainment
- 8 miles from Winchester
- Contact for rates
D D. said
“The face painting and balloon twisting were a hit. The kids had a great time. The artist was prompt, professional and made sure veery child got to participate in both activities. 10/10 would... ”
- Concord, MA
- Face Painter / Family Entertainment
- 11 miles from Winchester
- Contact for rates
Kim said
“Raddo was perfect in every way. Very professional, excellent at what he does. Will hire him in the future. The children loved the face painting and balloons. Very reasonably priced as well. ”
- Hyde Park, MA
- Face Painter / Family Entertainment
- 14 miles from Winchester
- Contact for rates
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... ”
Munsey's Magic
- Medford, MA
- Magician / Family Entertainment
- 3 miles from Winchester
- Contact for rates
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... ”
- Salem, MA
- Caricaturist / Family Entertainment
- 13 miles from Winchester
- $100 and up
Candice M. said
“Josh was very professional, easy to work with, and created awesome caricatures of our students for our school event! ”
- Chelmsford, MA
- Caricaturist / Family Entertainment
- 16 miles from Winchester
- $100 to $150 a hour
Joan C. said
“Dave,
Great job! You certainly were busy yet your grace prevailed.
Warm thanks.
Joan ”
- Chelmsford, MA
- Face Painter / Family Entertainment
- 16 miles from Winchester
- $95hr, + travel time
Katy K. said
“Sarah did a tremendous job and fans loved her face painting on the main concourse! It's a pleasure working with her. I highly recommend! ”
- Boston, MA
- Magician / Family Entertainment
- 8 miles from Winchester
- Contact for rates
Lorie K. said
“Peter O'Malley is a true magician. He engages the crowd and makes it fun for all. ”
- Boston, MA
- Magician / Family Entertainment
- 8 miles from Winchester
- $400+
Bradley S. said
“Tarek has an outstanding show and is excellent with the crowd. His magic was very interactive which was great for a party, and the whole show was well put together. He was very professional throughout... ”
- Randolph, MA
- Balloon Twister / Family Entertainment
- 21 miles from Winchester
- Contact for rates
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!! ”
- Arlington, MA
- Puppet Show / Family Entertainment
- 3 miles from Winchester
- $225 and up
Gloria L. said
“We had the absolute best experience with Margaret and her incredible puppet show! From the moment the show started, the kids were completely captivated—laughing, shouting with joy, and totally engaged... ”
- Wakefield, MA
- Face Painter / Family Entertainment
- 5 miles from Winchester
- $145 and up
Pat M. said
“Everything about the service was fantastic - punctual, accommodating and very talented. Wil definitely hire again! ”
- Cambridge, MA
- Face Painter / Family Entertainment
- 6 miles from Winchester
- $180 and up
Fiona H. said
“We had the pleasure of having Color Me Funky join us at the DDS-sponsored Family Fun Day at the beautiful Museum of Science along the Charles River, and we could not have been happier with the... ”
- Wilmington, MA
- Magician / Family Entertainment
- 7 miles from Winchester
- $300 and up
Ester D. said
“Really good! Everybody enjoyed the card tricks ”
- Boston, MA
- Caricaturist / Family Entertainment
- 8 miles from Winchester
- $150 per hour
Bhavin G. said
“John the caricaturist who attended the event was phenomenal . We were amazed by his ability to very creatively integrate a child’s preferred theme e.g. Star Wars, Disney Frozen, unicorn etc into the... ”
- Brookline, MA
- Magician / Family Entertainment
- 8 miles from Winchester
- $200 and up
Daniela K. said
“Oliver brought such great energy to my birthday party at my home! His tricks were amazing, and he was so charismatic and funny. I 100% recommend Oliver. ”
- Salem, MA
- Face Painter / Family Entertainment
- 13 miles from Winchester
- Contact for rates
Lauren M. said
“Trace was so amazing to work with. She was incredibly responsive, accommodating when we had to shift the party time due to weather, and did absolutely beautiful work. She made all of the kids feel... ”
- Quincy, MA
- Face Painter / Family Entertainment
- 15 miles from Winchester
- Contact for rates
Tim M. said
“She was ready to go when the guests arrived and received rave reviews from everyone ”
- Lowell, MA
- Face Painter / Family Entertainment
- 15 miles from Winchester
- Contact for rates
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. ”
- Stoneham, MA
- Puppet Show / Family Entertainment
- 3 miles from Winchester
- $250-350. travel fees may apply.
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... ”
- Malden, MA
- Caricaturist / Family Entertainment
- 4 miles from Winchester
- Contact for rates
Kathleen R. said
“Hello, all, Jeff Kesses had a table at the Eliot Church of Lowell MA 150th year anniversary on June 23, 2019. He set up his table, and did caricatures of church members, families and children as the... ”
- Somerville, MA
- Face Painter / Family Entertainment
- 5 miles from Winchester
- $125 and up
Kristin K. said
“Elizabeth was great—on time and lovely designs:) ”
- Cambridge, MA
- Photo Booths / Family Entertainment
- 6 miles from Winchester
- Contact for rates
Eddie R. said
“OMG this was way too much fun at my sons party. The printing of the pics and the digital boomerang videos were so cool. This is definitely something to have at any party. They cover any type of event.... ”
- Cambridge, MA
- Magician / Family Entertainment
- 6 miles from Winchester
- Contact for rates
Caroline O. said
“Edraz wowed everyone at my 30th birthday! His mix of comedy and magic was perfect and was the best addition to make the night unforgettable! ”
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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.