Halloween Window Painting is scheduled for Sunday, Oct. 19, from 9 a.m. to 3 p.m. It’s still a few weeks away, but not too early to start planning for this annual tradition that brings together friends and neighbors and a community spirit throughout Rye.
But parents beware: If you’re not prepared, Halloween window painting can be like a bad horror movie.
I like to think of mistakes as opportunities to learn, and over the years Halloween Window Painting has afforded me the chance to learn a lot! This is one of Rye’s favorite traditions, with 1,000 kids on Purchase Street painting windows and soaking in the Halloween season.
Here are some tips I’ve learned over the years — mostly from my own mistakes:
Mistake No. 1: I forgot to pick up the window location.
Nothing is less fun than having excited kids in the car with paintbrushes in hand and then realizing you don’t know where to take them. Don’t forget to pick up your assignment at Rye Rec a day or two before window painting. And if you do forget, the incredible Rye Rec staff are there to help.
Mistake No. 2: We had no idea what to paint when we arrived.
When the kid next to you has quickly turned out a 3-D cemetery scene, complete with rising ghosts and goblins, but 30 minutes in your kids are still staring at a blank window, the pressure starts to mount. So before the big day arrives, schedule a planning session. Get the two partners together to sketch out their idea (and work out their “debates”).
Mistake No. 3: We rushed.
A rushed painting ends up looking more like a blurry tie-dye T-shirt than a spooky Halloween masterpiece. Paint your window in two phases. First, paint the background using a large brush or roller. Then go enjoy all the sights and activities on Purchase Street (or head to soccer practice). Enjoy the treats provided by The Women’s Club of Rye Children’s Philanthropy. Listen to local bands play. Or get your face painted or enjoy the pumpkin carving.
After about an hour, come back to paint the main image.
Mistake No. 4: I didn’t dress for the mess — or the weather.
Wear old clothes (that includes you, parents!). No matter how careful kids are, paint has a way of getting everywhere. Also, consider the weather. I’ve been out in the freezing cold — and on beautiful, very warm fall days. I was always impressed by the parents who brought some folding chairs too (I never remembered this).
Mistake No. 5: I threw away supplies.
Rye Rec sells a kit of supplies. Buy them once and reuse them for years. Have your kids clean everything, put it on a shelf, and reuse it year after year. Keep all your supplies in one large storage box so it’s easy to pull out each fall. When your kids outgrow window painting, pass along your supplies to a younger family. It keeps the tradition going and makes another child’s day.
And after all of this, if you make mistakes, remember it’s all just part of the fun at Rye’s 72nd Annual Halloween Window Painting.
Liz Woods is the founder of Ryemarkable Moms.


