Use a hammer and pry bar to carefully remove the wood trim from around the inside of the window exposing the sash weight pockets.
Insulating window weight pockets.
Stack strips to completely fill the void.
Remove exterior flat casing to reveal weight pocket.
We use a router to grove the sides of the sash so that the sash can move along an interlocking metal track.
This old house general contractor tom silva shows an energy efficient way to insulate old windows.
Check the fit of the brick molding.
If there is a gap i would caulk it.
Insulating window weight pockets i am not 100 sure that just removing the casing will reveal the cavity.
I restore these windows for a living.
Use foil tape to seal the joint between the window jamb and foam insulation.
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These houses typically have no water management details around windows doors which works while the wall is open but will cause issues with insulation.
For window weight pockets i just blow out as much dust as possible then spray the area with water then canned foam the cavity.
It may be be covered with lath and plaster as well which would open up another can of worms.
I would not try to fill in the weight pockets with any insulation.
Then cut strips of 2 foam board to fit into the wieght pocket where the weights used to be.
I did this on several windows.