Doors, Windows & Shutters Workshop: October 15
At one time or another, most of us have thought about tackling a painting project around the house. And why not? DIY projects can be fun, efficient and cost-effective – if you know what you’re doing.
Well, here’s a great opportunity to hone your skills and learn from the pros!

~ Participant from our very first DIY class
Our upcoming DIY workshop – Doors, Windows & Shutters, Oh My! – will be held Saturday, October 15 from 9-11 a.m. at Stewart Painting’s headquarters in Hyannis. The cost to participate is just $10, 100% of which will be donated to the Cape & Islands United Way.
To get an insider’s perspective on these DIY classes, we spoke to Crew Leaders Jason Healey and Dennis “D.J.” Cain II. Jason and DJ have a combined 26 years experience in the industry, and in addition to their responsibilities out in the field, they co-lead both the DIY classes and Apprentice Boot Camps at Stewart Painting.
Here is a synopsis of our chat, detailing the program and what you can expect.
How did the Do It Yourself (DIY) classes at Stewart Painting come to be?
These classes are actually an extension of Sheldon’s participation on WXTK’s Handyman Hotline. On the show, he answers questions and provides general painting product and process information, and homeowners have a lot of great questions! It became clear that homeowners have a real interest in taking their questions to the next level by learning some hands-on techniques.
So, are homeowners the target audience for these classes?
The DIY classes are mostly homeowners, but they are appropriate for anyone who wants to learn the techniques. Sometimes people who are considering a career in painting or carpentry may attend just to check it out and “dip their toes” – if they want to go further they may consider the Apprentice Boot Camp.
What is the basic structure of a DIY class?
Classes are about two hours long. We start with coffee and donuts and a casual meet and greet, then we give an overview of what they’ll be doing that day. The class includes both listening/taking notes and doing hands on exercises.

Where do the classes take place?
Classes are held in the back of our offices in Hyannis, where Sheldon installed a facade specifically for classes and training. The facade has different surfaces, trim, hardware, etc., so participants are able to learn in a “real” environment. Everyone gets to use the tools and try their hand at whatever skill or technique is being discussed.
What are some of the skills people can expect to come away with?
It depends on the class, but some of the techniques we teach include: prep (sanding, taping, small repairs), the anatomy of a paint brush and how to hold/use it, and reviewing different products – so people can confidently choose the right ones for a specific project.
What other classes have been done in the past?
We’ve held DIY classes on how to paint a room, and how to paint cabinets, among others. We’re always open to suggestions, too. On the Handyman Hotline, questions have ranged from painting a garage floor to touching up trim. If you have a suggestion for a DIY class, please email us!
How do people sign up for the class October 15th?
Signing up is easy. We have an online sign up form that can be accessed here.
Upcoming DIY Class at a glance:
- What: Doors, Windows & Shutters, Oh My!
- When: Saturday, October 15th from 9-11 a.m.
- Where: Stewart Painting, 379 Iyannough Road (Route 28), Hyannis – behind Eastern Bank
- Cost: $10, 100% of which will be donated to Cape & Islands United Way