Fall Fun at Rollingwood!
Fall Fun at Rollingwood!
October 2026
What a wonderful start to the school year! September was filled with new friendships, joyful discoveries, and plenty of learning through play. It has been a pleasure watching our students settle into their classrooms, connect with their teachers, and grow more comfortable with their daily routines. Thank you for partnering with us to make the beginning of the year so special!
October brings cooler mornings, colorful leaves, and new opportunities to explore. Our classrooms will celebrate the season through nature discoveries, hands-on activities, creative art, and favorite fall stories. We’re especially excited to bring our school community together for our Book Character Parade and Fall Festival!
October 13 & 14: Picture Days
Laurie Bateman Photography will be taking individual student pictures indoors during the school day.
Tuesday, October 13: Students enrolled Monday through Friday and students enrolled Tuesday/Thursday.
Wednesday, October 14: Students enrolled Monday/Wednesday/Friday and staff.
Please check your child’s ClassDojo for classroom reminders. Picture packages and pricing will be emailed after your child’s pictures have been taken.
October 30: Book Character Parade & Fall Festival
Join us on Friday, October 30, beginning at 11:00 a.m., for storybook fun and fall festivities!
We’ll begin with our Book Character Parade! Families are encouraged to line up along the front lawn and Whitton Way to watch and cheer as our students parade out of the main entrance, across the stepping stones, and down the sidewalk to the cul-de-sac before returning for photos.
After the parade, we’ll continue the fun with a Not-So-Scary Trunk or Treat, followed by our very own Rollingwood Academy pumpkin patch, bounce houses, and more fall festivities!
All outdoor activities are weather permitting. Additional details, including arrangements for students who do not normally attend on Fridays, will be shared through ClassDojo.
Eight Parent Volunteers Needed for Trunk or Treat
Help us make Trunk or Treat extra special! We’re looking for eight parent volunteers to decorate their vehicles with fun, child-friendly themes. Rollingwood Academy will provide the treats. You bring the decorations and creativity!
If you would like to volunteer, please email info@rollingwoodacademy.com.
Book Character Costume Ideas
We invite students to dress as a favorite book character. Costumes can be simple, comfortable, and made from items you already have at home!
Pete the Cat: A yellow shirt, blue pants, colorful paper buttons, and cat ears.
If You Give a Mouse a Cookie: Overalls, mouse ears, and a cardboard cookie.
Madeline: A blue dress, red scarf, and yellow hat.
Fancy Nancy: Colorful dress-up clothes and fun accessories.
Where’s Waldo?: A red-and-white striped shirt, jeans, glasses, and a beanie.
The Very Hungry Caterpillar: A green outfit and an antenna headband.
Harold and the Purple Crayon: Pajamas and a large purple cardboard crayon.
Corduroy: Green overalls and bear ears.
Amelia Bedelia: A dress, apron, and a playful hat.
Pigeon: A blue shirt and a homemade pigeon headband.
Please choose costumes that allow your child to walk, play, and participate comfortably. Send the book that matches your child’s costume, labeled with your child’s name.
Classroom Pumpkin Decorating Contest
Our annual classroom pumpkin decorating contest is back! Each class will transform a pumpkin into a favorite book character.
The pumpkins will be displayed during our Fall Festival, and families will also have the opportunity to vote on our Facebook and Instagram pages that week. The class with the most votes will win a special classroom celebration!
November 2: Parent-Teacher Conferences
Parent-teacher conferences will be held on Monday, November 2, for all classrooms. School will be closed to students that day. These meetings are an opportunity to celebrate your child’s progress, share observations, and discuss goals together.
Teachers will share sign-up information through ClassDojo. Each appointment will be scheduled for 15 minutes. If the available times do not work for your family, please contact your child’s teacher to arrange an alternative.
Conferences are for parents and guardians only. Please arrange care for your child during your appointment.
Seasonal Reminders
As cooler weather arrives, please send a labeled jacket or sweater so your child can comfortably enjoy outdoor learning and play. Check that your child’s extra clothing is appropriate for the season, too.
Please help us keep our school community healthy by keeping children home when they are ill and following our school illness policy before returning. We’ll continue encouraging frequent handwashing and healthy classroom habits throughout the season.
Thank you for your continued support and for being part of our Rollingwood family. We can’t wait to celebrate fall with you! Follow us on Instagram and Facebook for classroom discoveries, school updates, and photos of the fun.
Warmly,
Rollingwood Academy