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I have a client that's looking for a full renovation for a June wedding. Last Fall I applied a weed control, most of the weed pressure was from Plantain. I'm planning on aerating and overseeding with a Fescue mix, but I was also thinking about putting down a perennial Rye for fast coverage. I'm concerned about the timing of the when to overseed and apply a pre-emergent, any advice would be appreciated. We're in zone 5 Western Ma.

just to add a bit more, i just saw you said your in western mass, im very close to you in central mass.

overseed, aerate, etc the 3rd week of april, maybe the 2nd week if spring is warm this year.

I’ve heard that adding some starter fertilizer and lime can give the new grass a boost. Maybe in cases like this, it's worth trying.
Also, make sure to adjust the watering so the ground isn’t too soft for guests walking around. It sounds like you’re doing everything you can to get the lawn looking great. And if the wedding party is getting all dressed up, it might be worth looking into some nice groomsmen's suits at https://www.gentlemansguru.com/product-category/wedding-tuxedos/. The right outfits can really pull everything together.

Aerate and overseed with Fescue now, and add perennial ryegrass for quick coverage. Just apply pre-emergent after the ryegrass has germinated to avoid inhibiting seed growth.

For your client's lawn renovation, aim to aerate and overseed with Fescue in early to mid-fall, around September or October, to ensure good establishment before winter. If you need quick coverage, consider adding perennial ryegrass a few weeks before the Fescue. Apply pre-emergent herbicide in early spring, as applying it too close to overseeding can prevent seed germination. Continue monitoring for weeds and use post-emergent treatments once the new grass is established.