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Caricaturists Winchester, MA

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32 Caricaturists serving Winchester, MA

Dave MacDonald

4.93 (149)
Top Performer
394 Verified bookings

  • Chelmsford, MA
  • Caricaturist
  • 16 miles from Winchester
  • $100 – $150 per hour

Megan R. said “We had a small “corporate” event of about 60ish people. Dave banged out tons of portraits for my employees and they all loved it! 10/10 recommend Dave and will hire again when needed. Thanks Dave!”

Caricatures by Josh

5.0 (9)
21 Verified bookings

  • Salem, MA
  • Caricaturist
  • 13 miles from Winchester
  • Starts at $100 per hour

Candice M. said “Josh was very professional, easy to work with, and created awesome caricatures of our students for our school event!”

Boston Caricature

5.0 (15)
Top Performer
28 Verified bookings

  • Boston, MA
  • Caricaturist
  • 8 miles from Winchester
  • $150 per hour

Colleen W. said “Great fast professional and above all FUN ! ”

  • Malden, MA
  • Caricaturist
  • 4 miles from Winchester
  • Contact for pricing

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
  • Contact for pricing

Note: gigsalad takes a % of the gross. You can book direct thru me. For the last 20 years I’ve been entertaining the masses up and down New England and...
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Kaleidoscope Artistic Entertainment

4.82 (162)
Top Performer
345 Verified bookings

  • Boston, MA
  • Children’s Party Entertainment / Caricaturist
  • 8 miles from Winchester
  • Contact for pricing

Kate T. said “Thea attended our annual family party at our assisted living and did resident/family portraits as keepsakes. The residents and families let me know how personable and professional she was, and we...”
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Boston Casino Events

1 Verified booking

  • Danvers, MA
  • Casino Party Rentals / Caricaturist
  • 13 miles from Winchester
  • Starts at $300

Entertainment/party rentals, specializing in Casino, Corporate and family parties of all types. You must visit our web site to see the unlimited things that...

Noa's Art Caricatures

5.0 (39)
Top Performer
54 Verified bookings

  • Rumford, RI
  • Caricaturist
  • 43 miles from Winchester
  • Starts at $250

Nicole L. said “Noa was an amazing addition to our housewarming celebration. Everyone who received a caricature and spent time with her raved about how cool she is... and we couldn’t agree more! She’s incredibly...”

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

48,380 quotes sent

In the past year, Caricaturists have sent 48,380 quotes to event planners.

7th most popular

Caricaturists rank #7 in popularity out of 539 categories on GigSalad.

4.9 out of 5 stars

There are 8,481 Caricaturist reviews on GigSalad with an average rating of 4.9 stars.

2.5 days on average to book

From request to booking, it takes 2.5 days (on average) to hire a Caricaturist.

Winchester ranks #69

Winchester is the 69th 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.