MacKID 2023 Back-to-School Guide to Westchester County

Extracurricular programs, local shopping, and more to get you first day ready!

By Kelly Fitzpatrick August 28, 2023

Get ready, families of Armonk - Chappaqua - Mount Kisco - Pleasantville and beyond! The countdown has begun, and the first day of school for your little ones in Westchester County is just around the corner. 

We've got you covered with the ultimate guide to kickstart the school year. Looking for school fun extracurricular programs in Westchester county?  School calendars in Armonk - Chappaqua - Mount Kisco - Pleasantville and beyond? Where to get your kid's back-to-school haircut or go back-to-school shopping in Northern Westchester? 

We have it all, plus advice and tips for dealing with that first-day anxiety, printables to make those first-day pics special, and even ideas on what to pack for lunch! Check it all out here:

Recommended Extracurricular Activities in Northern Westchester


UMAC Briarcliff

UMAC Shrub Oak

Rewilding School

Code Ninjas

East Coast Sports and Fitness

Soccer Shots Westchester

Steffi Nossen Dance Studio

Tot Time in North Salem

lisegagne | Canva

School calendars for Northern Westchester

Bedford Central School District
First day for Bedford: 9/5/23

Briarcliff Manor Union Free School District
First day for Briarcliff Manor: 9/8/23

Byram Hills School Calendar
First day for Byram Hills: 9/5/23

Chappaqua Central School District School Calendar
First day for Chappaqua: 9/5/23

Croton-Harmon Union Free School District

First day for Croton-Harmon: 9/5/23

Hendrick Hudson School District

First day for Hen Hud: 9/5/23

Katonah - Lewisboro School District

First day for Katonah-Lewisboro: 9/6/23

Lakeland Central School District

First day for Lakeland: 9/6/23

Mount Pleasant Central School District

First day for Mount Pleasant: 9/5/23

North Salem Central School District

First day for North Salem: 9/6/23

Ossining Union Free School District

First day for Ossining: 9/5/23

Pleasantville Union Free Central School District
First day for Pleasantville: 9/5/23

Somers Central School District

First day for Somers: 9/5/23

Yorktown Central School District
First day for Yorktown: 9/5/23

Community Back-to-School Events

Check back here frequently for updates as more events are added closer to the start of the school year!

Little Dreamers Back to School Aloha BBQ Tickets, Sat, Aug 19, 2023 at 12:00 PM

Glen Island Park, New Rochelle August 19th

Stay tuned to ride the wave of the next school year with a big Aloha BBQ! Our Back to School BBQ is the ultimate way to kick off the next fall academic season, with FREE school supplies and a mouth - watering spread of food, drinks and snacks. Plus, don't miss out on the fun games - we've got exciting activities and amazing giveaways that will keep you stoked all day long! Come join us on Saturday, August 19th and let's make this school year the best one ever.

Back-to-School Grab and Go

Yonkers Riverfront Library

All Day 8/21 - 8/25

We are eager to help kids get the next school year off to a great start, so we are offering a Back-to-School Grab and Go. There will be a pencil case, ruler, erasers, pencils, and a few other surprises. Available on the second floor while supplies last.

End-of-Summer Social at Chappaqua Library

August 23rd, 5:30 - 7:00 p.m.

Ice cream truck in the back parking lot, with music, hula hoops and beach balls. Drop in anytime between 5:30 and 7 PM- tickets for ice cream will be handed out as long as supplies last!

Newly Added:

Greenburgh Block Party Back to School Backpack Giveaway

White Plains

September 2nd

Back-to-School Bingo Grades K - 2 at Chappaqua Library

September 7th, 4:00 - 5:00 p.m.

Rounds of Bingo with a school theme to help children get back into the school mood.

Code Ninjas

Back-to-School Bash

Mount Kisco

September 9th, 1 - 5 p.m.

Open to the public! For all gamers and coders, as well as those that would like to learn more. Enjoy an afternoon of coding and robotics challenges, speedcubing, gaming, and more!

Know of a community back-to-school event we're missing? Add it to our Macaroni KID calendar now!

Pamela's Photo Poetry | Canva

Back to school haircuts in Armonk - Chappaqua - Mount Kisco - Pleasantville and Beyond

Looking for a great spot for a back-to-school haircut? 

Chappa Cuts Kids Salon

11 Memorial Drive, Chappaqua, NY 10514

Kid Styles Salon
701 North Bedford Rd, Bedford Hills, NY 10507

Know of a back-to-school haircut event or stylist special? Email with the details and we'll get it added!

 DAPA Images via Canva 

Back to school shopping in Northern Westchester

There are the big box stores, of course, but you can also support locally-owned businesses when doing your back-to-school shopping! Here are some of our favorite places for shopping for school supplies and clothes in our area that are locally owned:





Once Upon a Child


Value Drugs Briarcliff


Have a favorite locally owned spot for back-to-school shopping you don't see listed here? Email, and we'll get it added!

More tips to make this school year in Armonk - Chappaqua - Mount Kisco - Pleasantville a great one:

Fun School Themed Crafts

Helpful Websites for Kids

After School Snacks

Easy Weeknight Dinners

Off to College

🎨 DIY Back to School Wreath
🎨 Back to School T-Shirt
🎨 Homework Time Door Hanger
🎨 Homework Survival Kit
🎨 Spruce Up Your Bike for Back to School
🎨 Brighten Up Your Backpack with a DIY Rainbow
💻 Khan Academy - learn everything about everything!
💻 National Geographic For Kids - Explore our world and the creatures that live in it!
💻 Fact Monster - homework help and study tips for all subjects and grades!
🧀 No Bake Peanut Butter Balls
🧀 Apple Nachos
🧀 Easy Peanut Butter Roll Ups
🧀 Watermelon Granita
🧀 Ladybug Bites
🧀 Easy Star Biscuit Bites🧀Fruit and Veggie Flowers (with Dip!)
🍝 Rotisserie Chicken Soup
🍝 Easy Cheesy Please Me Chicken
🍝 Chicken Tortilla Casserole
🍝 Easiest Ever Pulled Pork
🍝Stuffed French Bread
🍝Easy Quesadillas
🍝5 Easy Dinners to Make with a Rotisserie Chicken
🍝Grilled Pizza
🍝One Meat, 5 Meals
📓 Last Minute Must Haves for College Dorm Rooms

Free Back-to-School Printables to Celebrate that First Day

5 Teacher-Approved Tips to Make Back-to-School Time Great
10 Books to Ease Back-to-School Fears 

Bento Box School Lunch Ideas