A Season of Gratitude at Rollingwood Academy
November 2026 | 2026–2027 School Year
October Memories
October brought plenty of learning, laughter, and fall fun! From Picture Days to our Fall Festival, we loved sharing these special moments with our Rollingwood community.
Our Book Character Parade brought favorite stories to life, followed by Trunk or Treat, bounce houses, pony rides, a hay maze, and pumpkins! Thank you to everyone who decorated a trunk, volunteered, donated treats, or joined the celebration. Your participation helped make the day so special for our children.
As we welcome November, we’re thankful for the friendships growing in our classrooms and the families who make Rollingwood such a caring place to learn.
Veterans Day
Rollingwood Academy will be closed on Wednesday, November 11, 2026, in observance of Veterans Day.
We extend our sincere appreciation to all who have served and continue to serve our country, especially the military families in our Rollingwood community. Thank you for your service and the sacrifices your families make. Our classrooms will explore age-appropriate ways to express gratitude and honor our veterans.
Cooler Weather Reminders
Our outdoor adventures continue as temperatures drop! Please send your child with a warm jacket and a labeled bag containing a hat and gloves to keep at school.
Please also check your child’s extra clothes and replace summer items with clothing suited to cooler weather. Labeling each item helps us return belongings to the right family.
Rollingwood Food Drive
This November, we’re partnering once again with the Foodbank of Southeastern Virginia and the Eastern Shore to collect nonperishable Thanksgiving food items for baskets to help families in need enjoy a Thanksgiving meal.
Suggested donations include canned vegetables, canned cranberry sauce, boxed stuffing, instant mashed potatoes, canned or packaged gravy, canned sweet potatoes, cornbread mix, and boxed macaroni and cheese. Please choose unopened, nonperishable items that are within their expiration dates.
The class that donates the most items will earn a special classroom party! Every donation helps and gives our children a meaningful opportunity to practice kindness and generosity.
Thank you for helping us fill Thanksgiving baskets for local families in need!
Salvation Army Stocking Drive
We’re hosting our annual Stuff a Stocking drive for the Salvation Army! Fill an empty stocking with small gifts and goodies to help bring Christmas joy to a child in need.
Please return filled stockings to Rollingwood Academy or any Dollar Bank location by December 4th.
Thank you for helping make the holiday season brighter for children in our community!
Thanksgiving Feast
Our annual Thanksgiving Feast will take place on November 20th at 12:00 p.m. Students will gather to share a meal, celebrate friendship, and reflect on the people and experiences they are thankful for.
Sign-ups for food donations and volunteer opportunities will be shared on ClassDojo. Tuesday/Thursday students are welcome to attend with a parent. Please arrive together at 12:00 p.m.
We look forward to sharing this favorite Rollingwood tradition!
Book Character Pumpkin Contest Winners
Congratulations to our Kindergarten class, our 2026 Book Character Pumpkin Contest winners! They will celebrate with a special classroom party.
Every class brought creativity and teamwork to its book-inspired pumpkin. Thank you to our teachers and students for their imaginative creations, and to our families and friends for voting and cheering them on!
Important Dates
November 11: Veterans Day (School Closed)
November 20: Thanksgiving Feast, 12:00 pm
November 24: Pizza Day (Please pack a snack)
November 25–27: Thanksgiving Break (School Closed)
December 18: Holiday Party, 12:00 pm
December 21–January 1: Winter Break (School Closed)
January 4: School Reopens