Why do chimneys leak where they meet the roof?
A chimney is a vertical wall sitting in the middle of a sloped roof, so water runs down the slope and meets it head on. The joint depends on flashing that can fail through rust, old sealant or movement, and on masonry that can crack, so there are several ways for water to get in.
Water has a straight run at the uphill side of a chimney, where it collects and pushes against the joint. That is why the high side is where many leaks begin, and why a cricket matters on a wide chimney. The two sides run water past the brick, and the downhill side has to shed it.
Masonry also soaks up water. A cracked crown, a loose cap or open mortar joints at the top of the stack let rain run down through the chimney and show up as damp near the flashing even when the flashing is fine. Sorting out which is which is the point of the first visit.
Is it a roofer or a mason who fixes a chimney leak?
Both can be involved. A roofer handles the flashing, the shingles around it and any cricket, while a mason handles the brick, the mortar joints and the crown. A roofer should tell you which of the two problems you have, and say so plainly if the masonry needs separate work.
The two trades meet at the counterflashing, which is set into the masonry and finished on the roof side. A roofer is comfortable cutting a groove into a mortar joint to seat it. Repointing a failing stack or rebuilding a crown is bricklayer's work, and it is not part of what the call line connects you with.
If you are told the chimney needs a mason, get that quote and the roofing quote lined up, because the order of the work matters. New flashing set into crumbling mortar will not last.
What is special about chimneys on older bay-area houses?
Older homes around Narragansett Bay often have large masonry chimneys, steeply pitched or multi-gabled roofs, and more than one roof covering. That means more metal to lay, more careful cutting and more places for earlier repairs to have been added over. Historic-district rules can affect the work.
East Greenwich's historic district has Colonial and Federal homes dating to the 1700s, and the Newport Historic District covers 250 acres of colonial and later houses. A house of that age has often been re-roofed more than once, and the area around the chimney is where layers and patches pile up.
Slate, wood shingle and standing-seam metal roofs need a roofer who is comfortable working around them. If your house sits in a locally designated historic district, the commission may have a view on the metal and the finish before work starts. Ask first.
Can chimney flashing be fixed in winter?
Often, but weather decides. Snow or ice around the chimney has to be cleared before metal can be fitted, and sealant and mortar work best when the day is not too cold or wet. A roofer may recommend a temporary cover and a full repair when conditions allow.
A leak in January does not wait for April. If the chimney is dripping now, a roofer may be able to cover it temporarily; the emergency roof tarping page explains how a tarp works as a stopgap. The permanent fix is scheduled when the roof can be worked on with care.
Meltwater is a common trigger. A chimney in an attic corner often stays cold, and melting snow around it runs into any gap the flashing has opened.