From a small family operation to one of the most trusted roofing companies in the Shenandoah Valley — here's how we got here.
Bailey Hughes started in 2012 when founder Mike Hughes decided to bring his 20 years of roofing experience back to his hometown of Winchester, VA. After working for large contractors across the East Coast, he wanted to offer something different — personalized service with the quality of a big company but the attention to detail of a local craftsman.
What started as a one-truck operation has grown into a team of 15 dedicated professionals, but our core values remain the same. We still treat every roof as if it were our own home, and we still believe that doing things right the first time is the only way to do business.
Today, we're proud to serve homeowners and businesses across the Shenandoah Valley, from Front Royal to Stephens City and everywhere in between. Every roof we install, every repair we make, and every inspection we conduct is backed by our commitment to excellence.
Our crew is our greatest asset. Each team member brings years of experience and a dedication to quality that you won't find anywhere else.
Founder & Master Roofer
With over 25 years in the industry, Mike founded Bailey Hughes to bring honest, quality roofing to Winchester. He's personally overseen over 2,000 roof installations.
Operations Manager
David manages day-to-day operations, ensuring every project runs smoothly. His background in project management means your job stays on schedule and on budget.
Sales Director
Jennifer handles estimates and customer relations. Her honest assessments and transparent pricing have earned her trust from hundreds of local homeowners.
Lead Installer
Roberto leads our installation crews with precision and care. His meticulous attention to detail ensures every shingle is perfectly placed.
These principles guide every job we do, from the smallest repair to the largest commercial project.
We'd rather take an extra day to do it right than rush through a job. Your roof is too important for shortcuts.
We'll tell you what you need — and what you don't. No pressure tactics, no unnecessary upsells.
We're part of this community. Our reputation depends on every roof we touch in Winchester and beyond.
When you call, you talk to a real person. We return calls within 24 hours — often the same day.
Whether you're ready to schedule a roof replacement or just have questions, we're here to help. Give us a call or stop by our office.
24 South Pleasant Valley Road
Winchester, VA 22601