🎄🎄🎄 This post is part of the 100 Days to Christmas challenge. Sept 16–Dec 25, we’re taking one small step a day to a lighter, happier holiday season. Join the free community 🎄🎄🎄
Somewhere between the first pumpkin spice latte and the last leftover turkey sandwich, the holidays always
Yesterday we set up your Holiday Planning Binder, and today we’re giving it a heartbeat: a holiday calendar printable. Think of this as your 1,000-foot view of the season..
This isn’t the time to cram in every tradition, cookie-baking day, or shopping trip — we’ll get there. For now, we’re laying down the skeleton the whole season will flow around: the dates that are already set in stone. Having them in place now means no surprises later, and it gives your binder a section you’ll come back to again and again between now and Christmas.
Why a Calendar Matters
The holidays are busy enough without trying to hold it all in your head. A calendar gives you:
- Clarity — you’ll see exactly how the season lays out and where your time is already spoken for
- Confidence — no more double-booking or scrambling last minute
- Calm — when the whole season is laid out in front of you, it feels a lot less overwhelming
Grab Your Calendar
Any blank monthly calendar works here — a wall calendar, a few printed pages, or something from a notebook you already own. A quick search will turn up plenty of free holiday calendar printable templates if you don’t already have one on hand.
Prefer not to design your own? As a member of the free 100 Days to Christmas community, you can grab ready-made Monthly Calendars at no cost — just print and go.
Either way, slide your calendar pages into your binder right behind your Fall & Halloween divider from yesterday.
Major Dates to Add
Here’s your ready-made list of key dates for this holiday season, so there’s no need to look them up:
- First Day of Fall: Tuesday, September 22, 2026
- Halloween: Saturday, October 31, 2026
- Daylight Saving Time Ends: Sunday, November 1, 2026
- Veterans Day: Wednesday, November 11, 2026
- Thanksgiving: Thursday, November 26, 2026
- St. Nicholas Day: Sunday, December 6, 2026 (optional, depending on family tradition)
- Hanukkah: December 4–12, 2026
- First Day of Winter: Monday, December 21, 2026
- Christmas Eve: Thursday, December 24, 2026
- Christmas Day: Friday, December 25, 2026
- Kwanzaa: December 26, 2026 – January 1, 2027
- New Year’s Eve: Thursday, December 31, 2026
- New Year’s Day: Friday, January 1, 2027
Other Events to Consider
Beyond the big holidays, think about anything already on the books that might eat into your planning or prep time:
- Birthdays (family, friends, coworkers)
- School events (concerts, plays, recitals, parent-teacher nights)
- Work events (holiday parties, conferences, big deadlines)
- Church or community events (bazaars, volunteer shifts, special services)
- Kids’ sports schedules (tournaments, practices, games)
- Travel days (family visits, weekend trips, airport runs)
- Doctor or dentist appointments already scheduled
- Anniversaries or family milestones
- Fundraisers or charity events
- Out-of-town guests visiting
The goal isn’t to micromanage — just to see where the non-negotiables are so everything else can plan around them.
Keep It Simple
Don’t overfill the calendar yet — leave white space. We’ll layer in traditions, shopping days, and self-care as the season goes. For now, just get the “already booked” dates on the page so they’re easy to see. This section of your binder is meant to grow with you — you’ll be adding to it all the way through December, not just today.
Tip: use one color for “must-do” items (holidays, concerts, travel) so they stand out from everything else you add later.
Today’s To-Do’s
- Print or grab blank calendar pages for September through December
- Slide them into your binder behind your Fall & Halloween divider
- Add the major holiday dates from the list above
- Fill in anything else you already know — school events, deadlines, birthdays, parties
- If you’re in GYST, add your call dates from Classroom
You’re Not Late — Jump In Anytime
Join the free 100 Days to Christmas community to get a new prompt every weekday, right where you are in the season.
That’s your 1,000-foot view in place. Next, we start zooming in.
