John Hunt Morgan’s raiders fought in Cynthiana twice, in July 1862 and again in June 1864. The town’s history shows in its older streets near downtown, and older roofs there leak in predictable places.
Chimneys, valleys and the joints where a roof meets a wall are the usual leak points on an older home. Flashing at those spots dries out, rusts or pulls loose. Replacing the flashing often stops the leak without a new roof.
Plumbing vent boots are another common source. The rubber collar around the pipe cracks in the sun and lets water run down the pipe into the attic. A new boot is a quick, inexpensive fix.
If the decking under a leak has gone soft, it needs to be replaced along with the shingles above it. Catching a leak early keeps the repair small. Waiting turns a patch into a section rebuild.