First Cubby

Preparing for the First Day of Preschool

By First Cubby Editorial · Updated 2026-07-01

The first day is a milestone for both of you. A little prep in the weeks before turns a scary morning into an exciting one.

In the weeks before

A comfort book you read together builds a goodbye ritual before day one.

“The Kissing Hand” (book)The classic read-together for separation anxiety in the first weeks of drop-off.View →

The morning itself

Skip Hop Zoo toddler backpackSmall enough for a 3-year-old to carry themselves — a big independence win on day one. The Zoo line is a preschool classic.View →Thermos Funtainer kids water bottleLabeled, easy for little hands to open, and hard to leave behind. The Funtainer stays cold and is famously leak-resistant.View →

Tears at drop-off are normal and usually stop minutes after you leave. Trust the teachers — this is their everyday.

If your program’s welcome packet includes a supply list, an early-childhood specialty store carries the arts, crafts, and classroom basics in one place.

Arts, crafts & classroom supplies — Discount School SupplyAn early-childhood specialty retailer for bulk arts, crafts, and preschool basics — where teachers and parents stock the room.View →

Frequently asked questions

How do I prepare my child for the first day of preschool?

Talk it up, read books about starting school, practice the goodbye routine, and shift to school-day sleep and meals about a week ahead.

How do I handle preschool separation anxiety?

Keep goodbyes short, warm, and confident. Tears usually stop minutes after you leave — trust the teachers, and build a goodbye ritual at home first.

How long does preschool separation anxiety last?

For most children it eases within the first few weeks as the routine becomes familiar. Persistent, severe distress is worth discussing with the teacher.

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Related guides

Preschool Supply Checklist: What to Pack for the First DayEverything a preschooler actually needs for day one — labeled and ready — without over-buyPotty Training for Preschool: What to KnowMany preschools require potty training before a child starts. Most kids are ready to beginKindergarten Readiness Checklist: Is Your Child Ready? (2026)Kindergarten readiness is more about independence and social skills than academics. Here’s

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