- Boston, MA
- Balloon Twister / Outdoor Party Entertainment
- 4 miles from Winthrop
- Contact for pricing
Jayasree A. said
“She did so good. She kept children occupied for almost 3hrs. ”
The 161 Best Outdoor Party Entertainers for hire in Winthrop, MA
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295 Outdoor Party Entertainers serving Winthrop, MA
- Boston, MA
- Balloon Twister / Outdoor Party Entertainment
- 4 miles from Winthrop
- $450 – $3,000 per event
Kathy M. said
“Linda was a great addition to our event and was super engaging with all of the children and adults alike. ”
- Wakefield, MA
- Face Painter / Outdoor Party Entertainment
- 10 miles from Winthrop
- Starts at $145
Frankie M. said
“Cheryl was amazing. So detailed, thoughtful, and precise in her work. All the kids loved her! ”
- Hyde Park, MA
- Face Painter / Outdoor Party Entertainment
- 11 miles from Winthrop
- Contact for pricing
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 was absolutely beautiful and she kept the kids... ”
- Andover, MA
- Juggler / Outdoor Party Entertainment
- 21 miles from Winthrop
- $500 – $3,500 per event
Donna M. D. said
“Did a good job keeping kids attention ”
- Boston, MA
- Juggler / Outdoor Party Entertainment
- 4 miles from Winthrop
- Contact for pricing
Itty P. said
“Danny did a wonderful job! He arrived on time, was easy going to work with and moved with the flow of our event. He provided fun LED Juggling entertainment and the crowd enjoyed it! ”
- Boston, MA
- Bubble Entertainment / Outdoor Party Entertainment
- 4 miles from Winthrop
- Starts at $375
Tapoya A. said
“The entire park enjoyed the bubble show and he paid special attention to the birthday girl so the kids were happy and I was happy lol he was very patient with the kids and kept them entertained. 10/10 ”
Rainbow Face Designs
1 Verified booking- Allston, MA
- Face Painter / Outdoor Party Entertainment
- 8 miles from Winthrop
- Contact for pricing
Hi! I’m Paula, a professional face painter serving Greater Boston and New England. I provide face painting for birthday parties, festivals, corporate events,...
- Burlington, MA
- Face Painter / Outdoor Party Entertainment
- 14 miles from Winthrop
- Contact for pricing
Candice R. said
“I was extremely happy with the service ”
- Danvers, MA
- Fire Performer / Outdoor Party Entertainment
- 14 miles from Winthrop
- Starts at $200
Jess B. said
“Unbelievable show! The entertainers communicated in advance and arrived A bit early to the event to set up and make sure that the performance area was ideal and safe. The show was over the top amazing... ”
- Concord, MA
- Face Painter / Outdoor Party Entertainment
- 19 miles from Winthrop
- Contact for pricing
Alysa K. said
“We had such an incredible experience! He was amazing with the kids, helped each one feel comfortable, and made the coolest designs! Our 4 year old and his friends had so much fun with all the... ”
- Brockton, MA
- Mobile DJ / Outdoor Party Entertainment
- 20 miles from Winthrop
- $700 – $4,000 per event
Sarah V. said
“We gave him a list of music we wanted to hear, and he gave us a great mix. Non-stop for the full time we had him, and he would take requests off the parameters we gave him with no problem! Would... ”
Kevin Kinetic
- West Newbury, MA
- Juggler / Outdoor Party Entertainment
- 29 miles from Winthrop
- Contact for pricing
Dr.gula said
“Kevin is one of the most professional performers I have ever met always on time always gives it his all and always kills it so if you want some amazing mind blowing juggling for any type of event... ”
- Chelmsford, MA
- Face Painter / Outdoor Party Entertainment
- 25 miles from Winthrop
- Starts at $95 per hour
Gina H. said
“Sarah was very communicative with logistics and very flexible when we had to move locations. She is very talented, adding unique flare and glitter to her designs. We almost couldn't fit all the kids... ”
- Lynn, MA
- Face Painter / Outdoor Party Entertainment
- 7 miles from Winthrop
- Starts at $100
Sam S. said
“Professional, kind, patient and prepared! Exceeded expectations! ”
- Randolph, MA
- Balloon Twister / Outdoor Party Entertainment
- 15 miles from Winthrop
- Contact for pricing
Emely A. said
“Thank you again Mr. Balloon Guy, for your great service during our community cookout! Children and adults alike love your creations. We love having you join us each year. Mr. Balloon Guy showed up... ”
- Cambridge, MA
- Face Painter / Outdoor Party Entertainment
- 6 miles from Winthrop
- Starts at $150
Lauren S. said
“We had such a great experience! Amazing artist, came on time, kind and friendly. I highly recommend. ”
- Salem, MA
- Face Painter / Outdoor Party Entertainment
- 11 miles from Winthrop
- Contact for pricing
Cheyanne B. said
“The Funky Brush did an amazing job at my daughter’s birthday party! We had a lot of kids, and she was able to paint them quickly, but the artwork was flawless. Lots of parents asked me for her info.... ”
- Lowell, MA
- Face Painter / Outdoor Party Entertainment
- 25 miles from Winthrop
- $150 – $175 per hour
Elizabeth K. said
“Kim did a wonderful job for my company outing. The kids and kids at heart really enjoyed her work! ”
- Lawrence, MA
- Mobile DJ / Outdoor Party Entertainment
- 25 miles from Winthrop
- Contact for pricing
Bonnie W. said
“We wanted to add something fun to a surprise 50th birthday party, and hiring a DJ was a great choice. Jimi was professional and easy to communicate with. I highly recommend All Pro Events DJS! ”
- Pawtucket, RI
- Balloon Twister / Outdoor Party Entertainment
- 40 miles from Winthrop
- Contact for pricing
Matt C. said
“Christine was fantastic to work with. We had lots of communication prior to the event and she did a fantastic job during the event and it was well received. We would definitely hire her again ”
- Boston, MA
- Mobile DJ / Outdoor Party Entertainment
- 4 miles from Winthrop
- Starts at $300
Erica A. said
“Djdamion did a great job and his price was very affordable! ”
- Boston, MA
- Fire Performer / Outdoor Party Entertainment
- 4 miles from Winthrop
- Starts at $375
Joe W. said
“I recently hired Katastrophi to provide fire art for the Somerville Open Studios weekend of art. She was extremely professional. I had never hired a fire artist before so she walked me through the... ”
- Boston, MA
- Face Painter / Outdoor Party Entertainment
- 4 miles from Winthrop
- Starts at $150
Jonathan K. said
“We had Characters do a Jedi party for us, and it was awesome! Both of our kids loved the Jedi master and Darth, who trained them to be Jedi knights. We appreciate them making the event fun and... ”
- Boston, MA
- Fire Performer / Outdoor Party Entertainment
- 4 miles from Winthrop
- Contact for pricing
Andrew P. said
“Had to cancel because of thunderstorms, but Kayla was extremely professional. Offered to come regardless, and even suggested the following day. ”
Flowy Jane
1 Verified booking- Boston, MA
- Fire Performer / Outdoor Party Entertainment
- 4 miles from Winthrop
- Contact for pricing
Through her unique blend of flow arts, modern dance, and freestyle movement, Flowy Jane creates captivating performances that articulate music and emotions in...
- Boston, MA
- Bubble Entertainment / Outdoor Party Entertainment
- 4 miles from Winthrop
- Contact for pricing
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 show. I had a lot of friends at the party asking... ”
- Boston, MA
- Stilt Walker / Outdoor Party Entertainment
- 4 miles from Winthrop
- Starts at $800
Ceasar M. said
“The performers were punctual and just blew the crowd away! Costumes were beautiful and the talented walkers were able to wow the crowd and engage in a way that will be memorable and everlasting!... ”
- Somerville, MA
- Face Painter / Outdoor Party Entertainment
- 6 miles from Winthrop
- Starts at $125
Kristin K. said
“Elizabeth was great—on time and lovely designs:) ”
DJ Remy P
1 Verified booking- Lynn, MA
- Mobile DJ / Outdoor Party Entertainment
- 7 miles from Winthrop
- Contact for pricing
Always bringing the vibe and creating the moment. Known for being a high-energy DJ, seamless blends, creative transitions and genre-bending sets that keep the...
- Quincy, MA
- Face Painter / Outdoor Party Entertainment
- 8 miles from Winthrop
- Contact for pricing
Amy Y. said
“Amazinggggg job. Everyone at the party was wow'ed by her artwork. Highly recommend, would definitely hire for a future party. ”
- Quincy, MA
- Balloon Twister / Outdoor Party Entertainment
- 8 miles from Winthrop
- $115 – $350 per event
Debra L. said
“Josef was incredible with the kids and provided such fun balloon twists for them! A charity event for the first event for Bikers Against Bullies, USA in the Northeast and Josef will be sure to be with... ”
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About booking Outdoor Party Entertainment in Winthrop, MA
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 Winthrop, Massachusetts 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 Winthrop 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 Winthrop, MA area
These Outdoor Party Entertainment serve the wider Winthrop and Suffolk county area and travel to Chelsea, Revere, East Boston, Charlestown, Boston, Everett, Nahant, Malden, Somerville, Cambridge, Roxbury Crossing, Saugus, Hull, Dorchester, Lynn, Roxbury, Medford, Melrose, Dorchester Center, Brookline Village, New Town, Brookline, Swampscott, Allston, Jamaica Plain, West Medford, Quincy, Mattapan, Arlington, and Brighton.