- Salem, MA
- Caricaturist
- 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! ”
The 11 Best Caricaturists for hire in Winchester, MA
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37 Caricaturists serving Winchester, MA
- Chelmsford, MA
- Caricaturist
- 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 ”
- Boston, MA
- Caricaturist
- 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... ”
- Malden, MA
- Caricaturist
- 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... ”
Designs by Dennis Caricatures
3 Verified bookings- East Weymouth, MA
- Caricaturist
- 19 miles from Winchester
- $75-$125
For the last 20 years I’ve been entertaining the masses up and down New England and throughout many states in North America. I use my background in fine art,...
- Boston, MA
- Children’s Party Entertainment / Caricaturist
- 8 miles from Winchester
- Contact for rates
Meagan K. said
“Lexi the Elf was fantastic! Highly recommend!! ”
- Boston, MA
- Children’s Party Entertainment / Caricaturist
- 8 miles from Winchester
- Contact for rates
Virginia K. said
“Snow White was beautiful, charming, and funny. We loved having her at our daughter's birthday! ”
- Boston, MA
- Balloon Twister / Caricaturist
- 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! ”
Estimate the cost
We’ve gathered average pricing for hiring Caricaturists in Winchester, MA using data from quotes sent through GigSalad.
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Quick facts for Caricaturists in Winchester, MA
47,085 quotes sent
In the past year, Caricaturists have sent 47,085 quotes to event planners.
6th most popular
Caricaturists rank #6 in popularity out of 539 categories on GigSalad.
4.9 out of 5 stars
There are 7,786 Caricaturist reviews on GigSalad with an average rating of 4.9 stars.
2.2 days on average to book
From request to booking, it takes 2.2 days (on average) to hire a Caricaturist.
Winchester ranks #65
Winchester is the 65th most popular city for Caricaturists requests in Massachusetts.
Popular events
Caricaturists are typically hired for Nonprofit Events in Winchester, MA.
Massachusetts ranks #5
Massachusetts is the 5th most popular state for Caricaturists requests in the United States.
Past events for Caricaturists in Winchester, MA
Non profit event
Caricaturist
5.0
March 26, 2026
2 hours
Dave was wonderful! Great communication and was a fun addition to the event! Would definitely hire him again.
Event total
$260
About booking Caricaturists in Winchester, MA
Caricatures are a really unique party entertainment option to keep your guests engaged. It also leaves them with a really fun souvenir to remember your event by. You can hire a caricature artist for all types of occasions from wedding receptions and birthday parties to corporate events and product launches. Find the perfect caricaturist on GigSalad!
The cost of hiring a professional caricaturist in Winchester, Massachusetts will vary depending on the number of guests, the detail of the drawing, and the artist’s skill level. Talented artists with years of experience drawing caricatures may charge more than those just starting out. Simple drawings in black and white will likely cost less than more elaborate art in color. Contact local caricaturists to get a quote customized for your event.
While browsing profiles for Winchester caricaturists, be sure to look through photos to get a feel for their artistic style. Read reviews from past clients to learn more about their experience working at events like yours. When talking with artists, discuss important details like expected guest numbers, venue setup, arrival times, and any other unique aspect of your event. If you’re hiring them for wedding entertainment or any other formal affair, you should also go over preferred attire.
Once you find the caricature artist you want to hire, finalize the booking through GigSalad. Our easy-to-use platform lets you communicate with artists, confirm your agreement, and make a secure payment all in one place. Every GigSalad booking is protected by our Worry-Free Guarantee so you can rest easy knowing we’ve got your back.
Caricaturists serving the Winchester, MA area
These Caricaturists 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.