Monthly Creative

I picked up painting again during quarantine in 2020, and it’s been a part of my life ever since

Dave Caolo (54 y) Painter Brewster

February 7, 2025
February 7, 2025

Meet Dave, a painter from Brewster who finds inspiration in the everyday—from the texture of a brick wall to the color of a crosswalk or the shape of a distant tree. His art is a window into his memories, reflections, and the moments that shape his world.

CC     Can you walk us through your journey as a creative? How did you get started, and what led you to where you are today?

DC     I've loved visual art and music since I was a child. When I was very young, I'd listen to the radio and find the tempo of any song that came on. Later I attended a high school with a great music department, but no visual art classes. I developed my music skills and went on to Berklee College of Music in Boston, but my interest in visual arts fell by the wayside. It wasn't until quarantine in 2020 that I started painting again. I fell in love with the process and expression, and I've been at it since.

I'm currently producing a series I'm calling "Skylights," with inspiration coming from the colorful, sunlit skies here on the Cape, as well as those I remember from time spent in rural upstate New York as a child.

CC     What are you working on these days?

DC     Today I'm working with watercolor and acrylics, with my main interest in abstraction. I'm compelled by the process of representing an idea, experience, relationship, etc. with a non-representational image. An abstract painting can be a narrative or a dialog with the viewer, and that's what I'm after.

I'm currently producing a series I'm calling "Skylights," with inspiration coming from the colorful, sunlit skies here on the Cape, as well as those I remember from time spent in rural upstate New York as a child.

CC     What does a typical day look like for you?

DC     I'm working a lot as I've got two kids in college. I put in 11 hours a day, Monday - Friday, and then a few hours on Sundays. It's challenging to find time to paint on that schedule, but I typically spend evenings and much of Saturdays either painting, sketching, or taking classes / workshops.

CC     What tools can’t you live without?

DC     The cart! I got a surplus wheeled cart from a school and I love it. It has an electrical outlet and two flat surfaces for storing just about everything I need while painting. I wheel it all around the studio with me. It's super convenient.  

As for materials I have a large wet palette that I use to keep paints fresh and usable for days; I'm always afraid I'll never be able to mix a certain color the same way again, so I make a lot of it.

I also have a Pilot Parallel pen that I use when sketching. It's got a calligraphy nib that I love because I can get thin lines or very heavy lines by simply adjusting the angle as I use it.

Finally, I have a watercolor sketchbook, some brushes and a mini palette of watercolors that I carry pretty much where ever I go.

Dave works from a corner in his basement, surrounded by walls covered in spray paint art—mostly his son's, who he allowed to practice legally down there. His easel sits in one corner, next to his trusty wheeled cart stocked with all his equipment

CC     What or who inspires you?

DC     Often colors, shapes, and patterns that I come across day-to-day. A scraggly tree against a door and a brick wall, the color of a crosswalk, anything really. I take photos of these things and put them in my "inspirations" folder.

When I'm painting, I'm typically inspired by my past. I consider my work to be a visual journal. I'll think of people I used to know, relationships either intact or defunct, or my responses to a moment in time. These are the things I want to depict.

I'm a self-taught artist who hesitates to even use the term in reference to myself.


CC     What would you like to learn more about in the future?

DC     Any and all of it. To be honest, I'm a self-taught artist who hesitates to even use the term in reference to myself. I didn't attend art school and haven't had any formal training outside of the art education I'm cobbling together myself via any class or workshop that'll have me. There is a strong sense of inferiority that creates a real tension for me. At times I'll feel I've made something worthwhile, but another part of me feels like I've wandered way from my place at the "kids' table" to where the adults are.

CC     What do you find most challenging as a creative?

DC    Finding time to create, but really the conflict I described in answering the previous question. I know art belongs to everyone, but I still wonder, "Do I really have the gall to do this?"


CC     What do you think creatives on Cape Cod could improve on?

DC     I'll start by sharing what I love: the sense of community. I've found that Cape Cod artists, curators, gallery owners, directors, etc. are welcoming, supportive, and ready to champion each other. That's been great.

As for improvements, I'd say the availability of classes and workshops after working hours. I realize that we have a large population of retirees on the Cape, and that's great. However I often find that educational opportunities for artists often accommodate a retiree's schedule. It's a bummer when I find an amazing class I'd love to take, only to realized it's scheduled for when I'm at work.


CC     What do you do when you're not working?

DC    Playing tabletop games. Everything from board games to card games to Dungeons & Dragons. I've been getting together with the same group of gamers every week for the past 15 years. It's a hobby I dearly love.

I'm also always reading a new book and stopping for coffee at The Snowy Owl in Brewster.

This interview was done over email.
Photography: Christine Johannessen

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