There is a website called "the vintage workshop" which has quite a few ideas for things on Mother's Day. You might want to take a peek at that site.

How about taking a photo of all the generations together. Have the photo either framed from each woman or printed onto a tote, apron or teeshirt for each?

How about copies of the original birth certificates of each person with children's pictures, various stages of growing up, even houses lived it, birthdays holidays and these could be on a single sheet or simple booklets.

Here's a partial idea. Find some pretty fabric and make something personal in that fabric to tie each generation together. For instance, the baby might have something small like a decorated bib. The baby's mother could have a tote bag or purse. Someone else could have a case for holding glasses, a scarf, or a decorated shirt.

How about a small shadow box frame with pics etc for each or just a large fram with pics etc for each?

Have you ever seen those Russian nesting dolls? Most of them have 5 or so different dolls that nest inside each other.

If you are handy with wood crafting, you could create your own. If you don't have enough time before Mother's Day or if, like me, you are not allowed to remain alone in a room with anything sharp that uses electricity (!), you could buy a set already made and re-paint them with the right hair color, glasses, etc., such that you have a doll that represents each generation.

What a joy to have five living generations of women!

Rain

(with one mother, three sisters, two nieces and a pregnant niece-in-law)

Here is a link that might be useful: matryoshka dolls

My mom is one of 11 kids and before grandma passed, they made shirts with all their generations on it, got everyone together with the shirts on and took a pic of all of them with the shirts on, then made a framed pic for everyone!