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The 115 Best Family Entertainers for Hire in Winthrop, MA

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190 Family Entertainers serving Winthrop, MA
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Kevin King - Magician / Family Entertainment in Boston, Massachusetts Featured vendor banner
Kevin King - Magician / Family Entertainment in Boston, Massachusetts

Kevin King

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4.96 (103)
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  • Map pin icon Boston, MA
  • Vendor category icon Magician / Family Entertainment
  • Travel distance icon 4 miles from Winthrop
  • Check mark icon 202 Verified Bookings

Emily F. said “Kevin was an awesome addition for our in-office family event! He engaged both kids and adults during the event and I received great feedback from others…”

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Colorful Creations - Face Painter / Family Entertainment in Boston, Massachusetts Featured vendor banner
Colorful Creations - Face Painter / Family Entertainment in Boston, Massachusetts

Colorful Creations

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4.69 (20)
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  • Map pin icon Boston, MA
  • Vendor category icon Face Painter / Family Entertainment
  • Travel distance icon 4 miles from Winthrop
  • Check mark icon 28 Verified Bookings

Erica M. said “Great service from start to finish. Prompt, clear, communication and fairly priced. Followed up with confirmations closer to our party date. Our "mermaid"…”

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Pop Art (Balloons by Dave) - Balloon Twister / Family Entertainment in Boston, Massachusetts Featured vendor banner
Pop Art (Balloons by Dave) - Balloon Twister / Family Entertainment in Boston, Massachusetts

Pop Art (Balloons by Dave)

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4.85 (23)
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  • Map pin icon Boston, MA
  • Vendor category icon Balloon Twister / Family Entertainment
  • Travel distance icon 4 miles from Winthrop
  • Check mark icon 46 Verified Bookings

Fritzie A. said “This is the 2nd year Victoria joined us for our party and she’s wonderful. We did glitter tattoos and balloon twisting. The kids couldn’t get enough!…”

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Great Scott Productions - Magician / Family Entertainment in Rockland, Massachusetts Featured vendor banner
Great Scott Productions - Magician / Family Entertainment in Rockland, Massachusetts

Great Scott Productions

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4.83 (53)
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  • Map pin icon Rockland, MA
  • Vendor category icon Magician / Family Entertainment
  • Travel distance icon 17 miles from Winthrop
  • Check mark icon 111 Verified Bookings

Lisa P. said “Scott was early, organized and ready to go! Had kids waiting inline before he got our of his car! The kids at our Backpack event for our Boston Community…”

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Mega Magic- Magician Mike D'Urzo - Magician / Family Entertainment in Boston, Massachusetts Featured vendor banner
Mega Magic- Magician Mike D'Urzo - Magician / Family Entertainment in Boston, Massachusetts

Mega Magic- Magician Mike D'Urzo

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5.0 (14)
  • Map pin icon Boston, MA
  • Vendor category icon Magician / Family Entertainment
  • Travel distance icon 4 miles from Winthrop
  • Check mark icon 10 Verified Bookings

Stephen T. said “• New out of the box thinking approach to delivering key motivational messages by combining magic with motivational speaking based on his real life experience…”

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Chris Herrick Magic - Magician / Family Entertainment in Boston, Massachusetts Featured vendor banner
Chris Herrick Magic - Magician / Family Entertainment in Boston, Massachusetts

Chris Herrick Magic

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4.98 (128)
  • Map pin icon Boston, MA
  • Vendor category icon Magician / Family Entertainment
  • Travel distance icon 4 miles from Winthrop
  • Check mark icon 64 Verified Bookings

Lidiane A. said “It was great, the kids had a really good time, Chris was very good with the kids and the adults also enjoyed the show!”

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Raddo - Face Painter / Family Entertainment in Boston, Massachusetts Featured vendor banner
Raddo - Face Painter / Family Entertainment in Boston, Massachusetts

Raddo

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4.79 (15)
  • Map pin icon Boston, MA
  • Vendor category icon Face Painter / Family Entertainment
  • Travel distance icon 4 miles from Winthrop
  • Check mark icon 2 Verified Bookings

Shauna B. said “Wonderful addition to our 4yr old’s birthday party. He was on time and did great work. Also, the kids loved him! Would definitely recommend and hire again.”

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Zanyacts - Balloon Twister / Family Entertainment in Boston, Massachusetts Featured vendor banner
Zanyacts - Balloon Twister / Family Entertainment in Boston, Massachusetts

Zanyacts

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4.98 (9)
  • Map pin icon Boston, MA
  • Vendor category icon Balloon Twister / Family Entertainment
  • Travel distance icon 4 miles from Winthrop
  • Check mark icon 6 Verified Bookings

Sabrina D. said “Our families at Fall Fest were so impressed by Linda.”

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Jeff Kesses / Formal Portrait and Caricature Artist - Caricaturist / Family Entertainment in Malden, Massachusetts Featured vendor banner
Jeff Kesses / Formal Portrait and Caricature Artist - Caricaturist / Family Entertainment in Malden, Massachusetts

Jeff Kesses / Formal Portrait and Caricature Artist

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4.55 (3)
  • Map pin icon Malden, MA
  • Vendor category icon Caricaturist / Family Entertainment
  • Travel distance icon 5 miles from Winthrop
  • Check mark icon 5 Verified Bookings

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…”

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Scribble Dibble - Face Painter / Family Entertainment in Hyde Park, Massachusetts Featured vendor banner
Scribble Dibble - Face Painter / Family Entertainment in Hyde Park, Massachusetts

Scribble Dibble

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5.0 (16)
  • Map pin icon Hyde Park, MA
  • Vendor category icon Face Painter / Family Entertainment
  • Travel distance icon 11 miles from Winthrop
  • Check mark icon 3 Verified Bookings

Meredith H. said “Regina came to my daughter’s birthday party early to set up, and was so patient accommodating all the kids and their face painting requests! Her work…”

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Ione Entertainment - Face Painter / Family Entertainment in Burlington, Massachusetts Featured vendor banner
Ione Entertainment - Face Painter / Family Entertainment in Burlington, Massachusetts

Ione Entertainment

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4.83 (20)
  • Map pin icon Burlington, MA
  • Vendor category icon Face Painter / Family Entertainment
  • Travel distance icon 14 miles from Winthrop
  • Check mark icon 45 Verified Bookings

Shelly F. said “She was awesome! The kids and parents had a great time and I would definitely recommend her!”

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The Donnino Mentalists - Beyond Imagination! - Magician / Family Entertainment in Westwood, Massachusetts Featured vendor banner
The Donnino Mentalists - Beyond Imagination! - Magician / Family Entertainment in Westwood, Massachusetts

The Donnino Mentalists - Beyond Imagination!

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5.0 (14)
  • Map pin icon Westwood, MA
  • Vendor category icon Magician / Family Entertainment
  • Travel distance icon 16 miles from Winthrop
  • Check mark icon 8 Verified Bookings

Kristin M. said “The Donnino Mentalists were the "entertainment" for our end-of-year holiday gathering for our team at work. Everyone loved the show! People…”

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Magic Fred - Magician / Family Entertainment in Lowell, Massachusetts Featured vendor banner
Magic Fred - Magician / Family Entertainment in Lowell, Massachusetts

Magic Fred

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5.0 (29)
  • Map pin icon Lowell, MA
  • Vendor category icon Magician / Family Entertainment
  • Travel distance icon 25 miles from Winthrop
  • Check mark icon 26 Verified Bookings

Sudha D. said “We had a great experience with Magic Fred during a birthday party for our 10 year old. Prior to the event he was very prompt and responsive. During the…”

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30 Second Studios - Photo Booths / Family Entertainment in Boston, Massachusetts Featured vendor banner
30 Second Studios - Photo Booths / Family Entertainment in Boston, Massachusetts

30 Second Studios

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5.0 (1)
  • Map pin icon Boston, MA
  • Vendor category icon Photo Booths / Family Entertainment
  • Travel distance icon 4 miles from Winthrop

Allandalefarm said “Bill's photo booth was a great addition to our public fundraiser event--he was kind and professional and the photos turned out beautifully. Really…”

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Munsey's Magic - Magician / Family Entertainment in Medford, Massachusetts Featured vendor banner
Munsey's Magic - Magician / Family Entertainment in Medford, Massachusetts

Munsey's Magic

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5.0 (62)
  • Map pin icon Medford, MA
  • Vendor category icon Magician / Family Entertainment
  • Travel distance icon 7 miles from Winthrop

Sujata P. said “I usually get bored in magic shows after a while, because either they are full of too much sound and bytes, or the magician is not humorous or because…”

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Beth Parkes Face Painting - Face Painter / Family Entertainment in Billerica, Massachusetts
Beth Parkes Face Painting - Face Painter / Family Entertainment in Billerica, Massachusetts

Beth Parkes Face Painting

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5.0 (23)
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  • Map pin icon Billerica, MA
  • Vendor category icon Face Painter / Family Entertainment
  • Travel distance icon 19 miles from Winthrop
  • Check mark icon 53 Verified Bookings

Sarah S. said “Beth was an amazing addition to our company picnic - everyone had an amazing time! I can't recommend her enough and hope to have her back at our…”

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Dave MacDonald - Caricaturist / Family Entertainment in Chelmsford, Massachusetts
Dave MacDonald - Caricaturist / Family Entertainment in Chelmsford, Massachusetts

Dave MacDonald

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4.92 (92)
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  • Map pin icon Chelmsford, MA
  • Vendor category icon Caricaturist / Family Entertainment
  • Travel distance icon 25 miles from Winthrop
  • Check mark icon 234 Verified Bookings

Daniel P. said “Dave does an excellent job and he is our go to for our family parties at our assisted living community in Concord. Always does quality work, is friendly/outgoing.…”

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The Improbubble Poppy! - Bubble Entertainment / Family Entertainment in Boston, Massachusetts
The Improbubble Poppy! - Bubble Entertainment / Family Entertainment in Boston, Massachusetts

The Improbubble Poppy!

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5.0 (4)
  • Map pin icon Boston, MA
  • Vendor category icon Bubble Entertainment / Family Entertainment
  • Travel distance icon 4 miles from Winthrop
  • Check mark icon 8 Verified Bookings

Felipe H. said “Very fun - great for kids birthday”

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Bubbles McGee - Bubble Entertainment / Family Entertainment in Boston, Massachusetts
Bubbles McGee - Bubble Entertainment / Family Entertainment in Boston, Massachusetts

Bubbles McGee

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5.0 (7)
  • Map pin icon Boston, MA
  • Vendor category icon Bubble Entertainment / Family Entertainment
  • Travel distance icon 4 miles from Winthrop
  • Check mark icon 9 Verified Bookings

Katya said “Melissa was great in every way, she was prompt, nice, energetic, funny and the kids (and adults) had the best time! I would highly recommend her bubble…”

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Mr Twister "The Balloon Guy" - Balloon Twister / Family Entertainment in Randolph, Massachusetts
Mr Twister "The Balloon Guy" - Balloon Twister / Family Entertainment in Randolph, Massachusetts

Mr Twister "The Balloon Guy"

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4.88 (31)
  • Map pin icon Randolph, MA
  • Vendor category icon Balloon Twister / Family Entertainment
  • Travel distance icon 15 miles from Winthrop
  • Check mark icon 58 Verified Bookings

Amy M. said “He arrived early, brought everything with him and was ready to go when we needed him to start. We had a large community event with around 200 people there…”

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Local Color Face Painting - Face Painter / Family Entertainment in Chelmsford, Massachusetts
Local Color Face Painting - Face Painter / Family Entertainment in Chelmsford, Massachusetts

Local Color Face Painting

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5.0 (2)
  • Map pin icon Chelmsford, MA
  • Vendor category icon Face Painter / Family Entertainment
  • Travel distance icon 25 miles from Winthrop
  • Check mark icon 3 Verified Bookings

Satenik K. said “Will definitely use her services again! Great work!”

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Balloon Lady Clown - Balloon Twister / Family Entertainment in Boston, Massachusetts
Balloon Lady Clown - Balloon Twister / Family Entertainment in Boston, Massachusetts

Balloon Lady Clown

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5.0 (23)
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  • Map pin icon Boston, MA
  • Vendor category icon Balloon Twister / Family Entertainment
  • Travel distance icon 4 miles from Winthrop
  • Check mark icon 48 Verified Bookings

Wendi B. said “Kristen was so wonderful with the children at our event, everyone one of them seemed to have a balloon in one shape or another in their hand. I would…”

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Todd Migliacci: Magician - Magician / Family Entertainment in Boston, Massachusetts
Todd Migliacci: Magician - Magician / Family Entertainment in Boston, Massachusetts

Todd Migliacci: Magician

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4.87 (3)
Top Performer badge
  • Map pin icon Boston, MA
  • Vendor category icon Magician / Family Entertainment
  • Travel distance icon 4 miles from Winthrop
  • Check mark icon 2 Verified Bookings

Joe M. said “Todd came to our summer camp, and we had an awesome show. He has material for kids, but also kept the staff entertained. We will have him back in the…”

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Boston Caricature - Caricaturist / Family Entertainment in Boston, Massachusetts
Boston Caricature - Caricaturist / Family Entertainment in Boston, Massachusetts

Boston Caricature

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5.0 (8)
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  • Map pin icon Boston, MA
  • Vendor category icon Caricaturist / Family Entertainment
  • Travel distance icon 4 miles from Winthrop
  • Check mark icon 14 Verified Bookings

Virginia O. said “Very professional and very nice . The guest had a good time and the caricature artist was so accommodating. Extreme talent and friendly . My 30th birthday…”

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Crazy Davy, Children's Magician - Magician / Family Entertainment in Melrose, Massachusetts
Crazy Davy, Children's Magician - Magician / Family Entertainment in Melrose, Massachusetts

Crazy Davy, Children's Magician

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4.99 (9)
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  • Map pin icon Melrose, MA
  • Vendor category icon Magician / Family Entertainment
  • Travel distance icon 7 miles from Winthrop
  • Check mark icon 18 Verified Bookings

Katie C. said “He exceeded my expectations for entertainment. The show was fun, funny and he had excellent control over a young audience. Everyone absolutely loved the…”

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Geminelle Designs - Face Painter / Family Entertainment in Quincy, Massachusetts
Geminelle Designs - Face Painter / Family Entertainment in Quincy, Massachusetts

Geminelle Designs

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5.0 (4)
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  • Map pin icon Quincy, MA
  • Vendor category icon Face Painter / Family Entertainment
  • Travel distance icon 8 miles from Winthrop
  • Check mark icon 5 Verified Bookings

Lisa G. said “Amazing work and wonderful personality! Would hire her again in a second!!”

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Glitter and Gore ™ - Face Painter / Family Entertainment in Quincy, Massachusetts
Glitter and Gore ™ - Face Painter / Family Entertainment in Quincy, Massachusetts

Glitter and Gore ™

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5.0 (8)
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  • Map pin icon Quincy, MA
  • Vendor category icon Face Painter / Family Entertainment
  • Travel distance icon 8 miles from Winthrop
  • Check mark icon 14 Verified Bookings

Rachael O. said “Rebecca did such a great job and brought so much joy to the kids after completing their requests! She didn’t even have pictures for kids to refer to!…”

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Margaret Moody Puppets - Puppet Show / Family Entertainment in Arlington, Massachusetts
Margaret Moody Puppets - Puppet Show / Family Entertainment in Arlington, Massachusetts

Margaret Moody Puppets

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5.0 (13)
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  • Map pin icon Arlington, MA
  • Vendor category icon Puppet Show / Family Entertainment
  • Travel distance icon 9 miles from Winthrop
  • Check mark icon 24 Verified Bookings

Hermiline P. said “My liberty Kids Preschool loved the puppet show. She arrived on time. The children enjoyed it. It was really fun and interactive.”

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The Magic of Joe Ferranti - Magician / Family Entertainment in Wilmington, Massachusetts
The Magic of Joe Ferranti - Magician / Family Entertainment in Wilmington, Massachusetts

The Magic of Joe Ferranti

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5.0 (18)
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  • Map pin icon Wilmington, MA
  • Vendor category icon Magician / Family Entertainment
  • Travel distance icon 15 miles from Winthrop
  • Check mark icon 26 Verified Bookings

Cassendra L. said “I hired Joe for my graduation party and it is a decision I am so happy I made! He got along with the guests so well and allowed us to interact with him…”

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Fancy Faces - Face Painter / Family Entertainment in Lowell, Massachusetts
Fancy Faces - Face Painter / Family Entertainment in Lowell, Massachusetts

Fancy Faces

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5.0 (17)
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  • Map pin icon Lowell, MA
  • Vendor category icon Face Painter / Family Entertainment
  • Travel distance icon 25 miles from Winthrop
  • Check mark icon 40 Verified Bookings

Lisa D. said “Kim was absolutely fantastic. Beautiful face painting, prompt, fast, great with kids. Worth every penny. She was the kiddos favorite part of the event!…”

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Family Entertainment in Winthrop, MA


Finding entertainment that’s full of variety and fun for all ages doesn’t have to be difficult. You just have to know where to start!

First, you’ll want to determine what your event needs. For small celebrations, strolling performers are a popular option for creating a fun atmosphere. For bigger gatherings, carnival games and inflatables are a big hit! Once you’ve determined what type of entertainment to book, search online for professionals in your area. Most entertainers and vendors have online profiles that show their services, and many offer various party packages to fit your budget. Check out performance descriptions and photos, and if possible, read through reviews from their past clients. When you’re ready to contact an entertainer for their rates and availability, make sure to give them as much information about your event as possible. Discuss important details such as performance space, power supply, expected number of guests, and any unique aspect of your event. The more info you give the professional, the easier it is for them to provide a customized quote. Lastly, confirm the agreement and details in writing. With GigSalad, everything you need to find and book family entertainment is in one simple platform. Browse profiles, get free quotes, and book with the added security of our Worry-Free Guarantee! Search for Family Entertainment in Winthrop, Massachusetts above.

Please note that these Family Entertainment may also travel to East Boston, Charlestown, Nahant, Roxbury Crossing, Hull, Dorchester, Roxbury, Dorchester Center, Brookline Village, New Town, Swampscott, Allston, Jamaica Plain, West Medford, Mattapan, Brighton, North Weymouth, Milton Village, Roslindale, Chestnut Hill, Waverley, Newton Corner, Arlington Heights, Hyde Park, East Weymouth, Newton Center, West Roxbury, Nonantum, Newtonville, and Lynnfield.

Find Family Entertainment in nearby cities

Chelsea Revere Boston Everett Malden Somerville
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