This post is part of the 100 Days ’til Christmas Challenge — one small step each day to make the holiday season less stressful and a lot more fun.
Yesterday we created our Holiday Planner (100 Days ‘Til Christmas), and today we’re zooming out for the big picture: your holiday calendar. Think of this as your 1000-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, I promise. For now, we’re laying down the skeleton of the season—the immovable dates that everything else will flow around. Having them in place now means no surprises later.
Why a Calendar Matters
The holidays are busy enough without trying to hold everything in your head. A calendar gives you:
- Clarity — You’ll see exactly how many weeks are left and where your time is already spoken for.
- Confidence — No more double-booking or scrambling last minute.
- Calm — When you can see the whole season laid out, it feels a lot less overwhelming.
Grab Your Calendar
You can use a wall calendar, planner, or digital tool like Google Calendar—whatever fits your style.
✨ If you’re a subscriber, you’ve got a head start: I created printable calendars for September through December so you can lay everything out at a glance. They can be found in the Holiday Hub
If your not a subscriber yet, feel free to sign up here! 👇
Major Dates to Add
Here’s your ready-made list of key dates for this holiday season (no Googling required):
- First Day of Fall: September 22, 2025
- Halloween: Friday, October 31, 2025
- Daylight Savings Time Ends: Sunday, November 2, 2025
- Veterans Day: Tuesday, November 11, 2025
- Thanksgiving: Thursday, November 27, 2025
- St. Nicholas Day: Saturday, December 6, 2025 (optional, depending on your family traditions)
- Hanukkah: Dec 14–22, 2025
- First Day of Winter: Sunday, December 21, 2025
- Christmas Eve: Wednesday, December 24, 2025
- Christmas Day: Thursday, December 25, 2025
- Kwanzaa: Dec 26, 2025 – Jan 1, 2026
- New Year’s Eve: Wednesday, December 31, 2025
- New Year’s Day: Thursday, January 1, 2026
Other Events to Consider
Beyond the big holidays, think about events that might eat into your planning or prep time. If they’re already on the books, get them on your calendar now:
- 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/dentist appointments already scheduled
- Anniversaries or family milestones
- Fundraisers or charity events
- Out-of-town guests visiting
The goal isn’t to micromanage. It’s just to see where the non-negotiables are so you can plan everything else around them.
Keep It Simple
Don’t overfill the calendar yet—leave white space. We’ll layer in the fun traditions, shopping days, and self-care later. For now, highlight these “already booked” dates so they’re easy to see.
Tip: Try using one color for “must-do” items (holidays, concerts, travel) so they stand out.
Quick Wins for Today
- Print or open your calendar.
- Add in the major holiday dates.
- Plug in any known events from the memory-jogging list.
- Keep your calendar handy—we’ll be narrowing in as the countdown continues.
Wrap-Up
That’s it—you now have your 1000-foot view of the season! With this big-picture framework in place, the rest of our planning will feel a lot more manageable.
Tomorrow, we’ll start zooming in. 🎄
👉 Don’t forget—if you’re not signed up yet, grab your free printable calendars for September through December so you can follow along with us.
