- Boston, MA
- Balloon Twister / Outdoor Party Entertainment
- 8 miles from Winchester
- $450-$3000 depending on travel distance/ style
Elizabeth T. said
“Fantastic!!! My kids loved the balloons and energy. ”
The 131 Best Outdoor Party Entertainers for hire in Winchester, MA
0%
Just a couple more things…
We need some additional information to ensure we find the perfect talent for your event!
299 Outdoor Party Entertainers serving Winchester, MA
- Boston, MA
- Balloon Twister / Outdoor Party Entertainment
- 8 miles from Winchester
- Contact for rates
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!... ”
- Hyde Park, MA
- Face Painter / Outdoor Party 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... ”
- Andover, MA
- Juggler / Outdoor Party Entertainment
- 14 miles from Winchester
- $500-3500
Candice H. said
“The performance exceeded our expectations. Students were completely engaged. I would highly recommend Bryson for his professional, ease to communicate with, flexibility, engagement of students and a... ”
- Burlington, MA
- Face Painter / Outdoor Party 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
- Juggler / Outdoor Party Entertainment
- 8 miles from Winchester
- Contact for rates
Brigitte B. said
“Danny is an incredible performer. He and his colleague put on a show that blew the audience away! From the costumes to the performance pieces themselves everything was 5 star worthy! They truly... ”
- Boston, MA
- Bubble Entertainment / Outdoor Party Entertainment
- 8 miles from Winchester
- $375 and up
Zarina O. said
“Kids loved it ”
- Concord, MA
- Face Painter / Outdoor Party 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. ”
- Danvers, MA
- Fire Performer / Outdoor Party Entertainment
- 13 miles from Winchester
- $200 and up - highly dependent on performance
Michael H. said
“Fire Amusement pout on a FANTASTIC show for us!! They were timely and respectful, and the show was GREAT!! ”
- Chelmsford, MA
- Face Painter / Outdoor Party Entertainment
- 16 miles from Winchester
- $95hr, + travel time
Elif E. said
“We hired Sarah as a face painter for my 8 yo daughter's birthday party. Sarah was very clear and professional in all her communications prior to the event, showed up to the event early and... ”
Motitas
1 Verified booking- Lynn, MA
- Face Painter / Outdoor Party Entertainment
- 10 miles from Winchester
- $100 and up
🎨 Professional face painter with over 10 years of artistic experience, specializing in fun, colorful, and creative designs for children’s parties, school...
- Randolph, MA
- Balloon Twister / Outdoor Party 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!! ”
- Wakefield, MA
- Face Painter / Outdoor Party Entertainment
- 5 miles from Winchester
- $145 and up
Dana N. said
“We had Cheryl back for the second year in a row for my daughter’s birthday (a bunch of 4-7 year olds). She did an incredible job!! Her face painting was beautiful and she was able to get to everyone... ”
- Cambridge, MA
- Face Painter / Outdoor Party Entertainment
- 6 miles from Winchester
- $150 and up
Marisa S. said
“It was a pleasure having Color Me Funky at our annual Pride event. Beautiful face painting, friendly interactions, and efficient painting so everyone got to join in! ”
- Salem, MA
- Face Painter / Outdoor Party Entertainment
- 13 miles from Winchester
- Contact for rates
Corrine said
“Amazing job,amazing person great with kids just the sweetest person ever love her work she literally went above and beyond to make every guest feel beautiful and confident I will be booking again... ”
- Lowell, MA
- Face Painter / Outdoor Party 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. ”
- Somerville, MA
- Face Painter / Outdoor Party Entertainment
- 5 miles from Winchester
- $125 and up
Kristin K. said
“Elizabeth was great—on time and lovely designs:) ”
- Boston, MA
- Stilt Walker / Outdoor Party Entertainment
- 8 miles from Winchester
- $800 and up
Cheryl B. said
“you were fabulous. Everyone was in awe of the living snowglobe. So professional and artistic. Highly recommend. ”
- Boston, MA
- Fire Performer / Outdoor Party Entertainment
- 8 miles from Winchester
- Contact for rates
Andrew P. said
“Had to cancel because of thunderstorms, but Kayla was extremely professional. Offered to come regardless, and even suggested the following day. ”
- Boston, MA
- Mobile DJ / Outdoor Party Entertainment
- 8 miles from Winchester
- $300 and up.
Erica A. said
“Djdamion did a great job and his price was very affordable! ”
Flowy Jane
1 Verified booking- Boston, MA
- Fire Performer / Outdoor Party Entertainment
- 8 miles from Winchester
- Contact for rates
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
- Fire Performer / Outdoor Party Entertainment
- 8 miles from Winchester
- $375 and up
Jonathan B. said
“Prior communication was professional. She showed up on time and her safety standards were great. I look forward to working with her in the future! ”
- Boston, MA
- Face Painter / Outdoor Party Entertainment
- 8 miles from Winchester
- $150 and up
Lisa M. said
“First of all I just loved working with this company. From my very first phone call to the last I knew my party was in good hands. They were so helpful and so great to work with. I was very... ”
- Boston, MA
- Bubble Entertainment / Outdoor Party Entertainment
- 8 miles from Winchester
- Contact for rates
May T. said
“Our 4yr olds party came together last minute and Melissa couldn’t have been more flexible and accommodating. The bubbles exceeded our expectations and the attention occupied by the kids was beyond.... ”
French KonXion Entertainment
1 Verified booking- North Reading, MA
- Mobile DJ / Outdoor Party Entertainment
- 9 miles from Winchester
- $500 - 2500
DJ J-Rock of French KonXion Entertainment provides professional DJ and MC services for weddings, corporate events, birthdays, private parties, and cultural...
- Jamaica Plain, MA
- Face Painter / Outdoor Party Entertainment
- 10 miles from Winchester
- $150 and up
Jj said
“McKenzie truly impressed us this weekend! Our 3-year-old daughter had an absolute blast with her friends, thanks to the incredible face art crafted by McKenzie. Her professionalism and top-notch... ”
Ocg Productions
1 Verified booking- West Roxbury, MA
- Mobile DJ / Outdoor Party Entertainment
- 12 miles from Winchester
- Contact for rates
I'm a diversified successful vocalist/entertainer that's appealing to all age groups. I bring enjoyment and memories for Senior Citizens and rip roaring fun...
- West Roxbury, MA
- Bubble Entertainment / Outdoor Party Entertainment
- 12 miles from Winchester
- Contact for rates
Katie K. said
“Poppy came to a school picnic at a park and was a total hit! The kids loved all her amazing bubble gear and were fully entertained for the entire 40ish minute show. ”
- Tewksbury, MA
- Mobile DJ / Outdoor Party Entertainment
- 12 miles from Winchester
- Contact for rates
Julie S. said
“My birthday party was a great time, and Ken and the music he played made it even better. I will definitely refer Ken to others and plan to book him again for any future events. ”
- Beverly, MA
- Face Painter / Outdoor Party Entertainment
- 15 miles from Winchester
- Contact for rates
Judy B. said
“Kimberly, is extremely talented and was enjoyable to work with! Kimberly’s price was very reasonable too! I would highly recommend her service and would use her again! Some pics of her work... ”
- Quincy, MA
- Face Painter / Outdoor Party Entertainment
- 15 miles from Winchester
- Contact for rates
Doreen R. P. M. said
“The children loved it and a few adults as well. We will use Glitter and Gore for our next event, and the next and the next. ”
- Quincy, MA
- Face Painter / Outdoor Party 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 ”
Start getting quotes
Tell us what you need and we’ll match you with the best options for your event. Receive messages and free, no-obligation quotes from interested talent right away.
Book with confidence
When you hire a Winchester Outdoor Party Entertainer through GigSalad, you’re backed by our Worry-Free Guarantee. From secure payments to reliable support, we’ve got your back.
You might also like
About booking Outdoor Party Entertainment in Winchester, 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 Winchester, 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 Winchester 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 Winchester, MA area
These Outdoor Party 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.