- 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 133 Best Outdoor Party Entertainers for hire in Winchester, MA
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299 Outdoor Party Entertainers serving Winchester, MA
- Boston, MA
- Balloon Twister / Outdoor Party 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.... ”
- Boston, MA
- Balloon Twister / Outdoor Party 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! ”
- Andover, MA
- Juggler / Outdoor Party Entertainment
- 14 miles from Winchester
- $500-3500
Leah C. said
“Bryson was a pleasure to work with, came nice and early to set up, entertained all ages from preschool through middle school, pulled up kids from the audience, and everyone had a great time! ”
- 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
- Face Painter / Outdoor Party 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... ”
- 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... ”
- 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!! ”
- 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... ”
- Chelmsford, MA
- Face Painter / Outdoor Party 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! ”
- 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
Pat M. said
“Everything about the service was fantastic - punctual, accommodating and very talented. Wil definitely hire again! ”
- Cambridge, MA
- Face Painter / Outdoor Party 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... ”
- Salem, MA
- Face Painter / Outdoor Party 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 / 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 ”
- 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. ”
- Woburn, MA
- Mobile DJ / Outdoor Party Entertainment
- 2 miles from Winchester
- $450 - $1750
Sylvia K. said
“Lee was very professional and easy to work with ! Choice of music was perfect ! ”
- 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
- 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
- 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.... ”
- 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
- 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
- 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... ”
- 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
Anne A. P. M. 5. said
“Excellent face painter, the best I have ever seen! ”
- Quincy, MA
- Balloon Twister / Outdoor Party Entertainment
- 15 miles from Winchester
- $115-$350
Laleh said
“He was in the event on time and kids had lots of fun with his balloons. Thank you! ”
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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.