Save a Roof, Call a Cowboy
20 Years of Roofing Excellence: Expert Solutions for Commercial and Residential Repairs.
About Us
Teamed up with Elk Contracting to offer top-tier roofing solutions across Texas Hill Country. A partnership with an award winning team built on quality and trust.
Welcome to Cowboy on Your Roof – a roofing company built on trust, expertise, and a legacy of excellence. As a second-generation roofer, I carry forward the values and skills passed down from my father, who boasts over 50 years of experience in commercial and residential roofing. With two decades of my own hands-on experience, I’ve honed my craft to offer you the highest quality roofing solutions.

We provide a service that is very much needed in roofing and we provide maximum services


Following in his footsteps, I bring over 20 years of personal experience in residential and commercial roofing. I have led sales at every company I’ve worked for, holding roles as a general manager, sales manager, and senior sales representative. Each year, I proudly complete over 100 residential projects and several commercial projects, maintaining an average closing rate of over 80% while generating my own leads.
Serving San Antonio, Texas Hill Country and surrounding rural communities, over to Sugar Land, down to the Coast and beyond
This is the reason why many people use our services
I specialize in all types of roofing systems, including durable and aesthetically stunning standing seam lifetime metal roofs. Partnering only with top-name manufacturers who stand behind their materials, I ensure that every project is built to last. One of our trusted suppliers, Atlas Roofing, provides industry-leading materials that meet the highest standards.

Give Us Feedback
Insurance job
Dennis made our insurance job very easy to understand. His crews from Elk were clean and efficient. We have a warranty on our roof now.
Tarped my roof before more water cane
He installed free tarping and will be back to meet the insurance company. Really nice guy.
Roofed our historic business
What a job Elk Contracting did along with Dennis Garrett installing a new metal roof over our historic downtown building/ We now have a lifetime roof. No more worries when we hear about storms rolling in !!!!
I was treated like royalty
Dennis Garrett drove 4 hours to help me out of a bind when my other roofer dropped the ball. His crew was amazing and he upgraded me to a better roof for no charge. I now have a black class 3 roof that my homeowners insurance loves…they gave me a discount for installing this system.
Roofed our 6500 sq ft home in 2 days. He also upgraded us from a 30 year roof to a 50 year roof at no additional charge..
Dennis quoted our Roof $4500 lower than the other company did.. he used a better product. His crew was in and out in two days. Our landscape was spotless and we love our new roof. We highly recommend the cowboy.