Tracking down hidden flashing failures behind a wide masonry chimney was the focus of our team on a home in Williamsburg, Virginia. During a recent Roofing for Reel walk-through, Brian Chalsma highlighted an issue that many local homeowners encounter: persistent leaks pooled right behind the chimney.

The Problem

Wide chimneys look classic, but they create a major barrier for water rushing down your roof line. On this specific Williamsburg roof, a slope runs straight down behind a very wide chimney. Because of a tricky pitch transition right before the back of the chimney structure, previous contractors skipped installing a proper diversion system. Without a clear path to go around, rainwater and organic debris collect directly against the brick wall, slowly seeping into the decking below.

The Technical Why

When a roof's slope meets a flat brick barrier, it acts like a dam. The correct solution is installing a cricket—a small, peaked double-sloped structure built onto the high side of a chimney designed to divert water to either side.

Because this roof featured a pitch transition right at the chimney's rear wall, framing a standard shingled cricket was a complex task. While you can build a timber frame and shingle over it, an exposed metal cricket (often formed out of durable metal or copper) provides a smoother surface. This keeps pine needles, leaves, and coastal downpours sliding past the masonry without pooling.

Professional Advice

If your home features a wide chimney, taking proactive steps can save thousands in internal water damage repair:

  • Inspect the High Side: Visually check the area behind your chimney from the ground or during routine gutter cleanouts for leaf buildup or standing moss.

  • Check the Pitch: Ensure any transition slopes have an adequate diversion channel installed rather than flat flashing covered in sealant.

  • Opt for Low-Maintenance Materials: Choosing an exposed metal cricket helps prevent debris accumulation in heavy-tree areas across Tidewater Virginia.

Whenever you're ready to inspect your chimney flashing or need a second pair of eyes on an ongoing leak, our local team is here to help. Give us a shout at 757-867-6600 or fill out the form on this page.