The spring before kindergarten
Most US districts hold kindergarten registration in the spring (typically March or April) of the year before kindergarten begins. The printed academic-year overview for the upcoming kindergarten year is the right anchor for the readiness plan: it shows the first day of school, the federal holidays, and the natural rhythm of the year that the child will be entering.
The summer before
The right summer plan for a soon-to-be kindergartener is rhythm, not academics. Print the June, July, and August monthly calendars. Mark a small daily routine — outdoor play, story time, lunch, rest, snack — and let the calendar carry it. By the end of August the child will have practiced the rhythm of a school day for two months without ever having been in a classroom.
Two weeks before the first day
Most districts hold a kindergarten orientation or meet-the-teacher event two weeks before classes begin. Print the August calendar and mark the orientation date, the first day of school, the bus stop time, and the school's first-week dismissal time (often early). For working families this is the most important two-week stretch of the year for childcare planning.
The first month
Print the September monthly calendar and use it as a working document. Mark the dates of half-day Wednesdays (common in many districts), the first PTA meeting, picture day, and any other early events. Kindergarten parents almost universally underestimate the volume of paper and dates that come home in the first month; the printed calendar is the most reliable place to capture them.
The first break
Most kindergarteners hit a fatigue wall around the first week of October — six weeks of full-day school is genuinely tiring for a five-year-old. The printed calendar should show the Columbus Day weekend or the local fall-break window in mid-October as a planned recovery weekend, not as an extra activity weekend. The recovery weekend is what carries the child through to Thanksgiving.