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Previous Events and VLOGs!

Rob Orpilla has been running booths at various events since 2017, starting in Massachusetts 

and expanding throughout the New England Area - occasionally traveling around the country. 

From town festivals, cons, celebrations, and private events such as weddings and birthdays.

He draws on-the-spot sketches of faces, caricatures, celebrities, fictional characters, pets, or anything else you can think of!

Stop by for a fun conversation and take some something special.

If you'd like to hire Rob for your own event, please contact him at

Video Recaps

Enjoy a select few videos from past events.

You can view more of these on YouTube.

2023 EVENTS:

Click the title of each event for their website/ additional information.


This event requires purchasing a ticket in advance!

Atlanta, GA

May 25th - Starting @ 2:00pm

May 26th - Regular Booth

May 27th - LIVE PANEL @ 5:30pm

May 28th - LIVE PANEL @ 2:30pm

Small Town Pride

North Brookfield, MA

June 24th @ 12:00pm to 6:00pm

Harwich Cranberry Festival I

Harwich, MA

July 8th @ 9:00am to 4:00pm

July 9th @ 9:00am to 4:00pm

Massachusetts Renaissance Faire

Cummington, MA

August 5th @ 10:00am to 7:30pm

August 6th @ 10:00am to 7:30pm

Holden Days

Holden, MA

August 26th @ 9:00am to 3:00pm

stART on the Street

Worcester, MA

September 17th @11:00am to 6:00pm

2022 EVENTS:

Grafton Pride [EVENT PASSED: Click for VLOG!]

Summer Tasting Party! [EVENT PASSED: Click for VLOG!]

Small Town Pride [EVENT PASSED: Click for VLOG!]

The Harwich July Arts Festival [EVENT PASSED: Click for VLOG!] 

NoWoCo Pride [EVENT PASSED: Click for VLOG!]


Massachusetts Renaissance Faire [EVENT PASSED: Click for VLOG!]

The Harwich August Festival [EVENT PASSED]

Holden Days [EVENT PASSED]

stART on the Street [EVENT PASSED]

Belchertown Fair [EVENT PASSED]

Conway Festival of the Hills [EVENT PASSED]

Columbus Day Weekend Craft Festival [EVENT PASSED]

Pecorino Outdoor Tasting [EVENT PASSED]


New England Craft and Specialty Food Fair [EVENT PASSED]

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