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.
The end of September always feels like a turning point. The mornings are cooler, the pumpkins are stacked high at the grocery store, and if you listen closely, you’ll hear kids whispering about costumes and candy. Summer is officially in the rearview mirror — and the Halloween season is here.
This is when the holidays start to pick up speed. It’s not just about Halloween (though that’s a big part of the fun) — it’s the first marker that we’re heading into a season full of traditions, family gatherings, and a lot of to-dos. Taking a little time now to reset before October hits will make the weeks ahead feel a lot smoother.
✅ September Calendar Check-In
Back on Day 99, we filled in our September calendars together to get the ball rolling. Now it’s time for a quick reflection:
- Pull out your September calendar.
- Circle the things you crossed off.
- Put a star next to what still needs attention.
- Move unfinished tasks into October so they don’t get lost in the shuffle.
This isn’t about perfection — it’s about progress. Even if you didn’t check every box, you’ve moved the needle forward. That’s worth celebrating.
📌 Need a little inspiration? I created a filled-in sample version of the September calendar that shows exactly what we covered every day so far. This will be in the Holiday Hub. If you haven’t signed up for the newsletter yet, go ahead and do so below and then you will get all printables and resources for the entire 100 Days ‘Til Christmas Challenge!
🎃 Kicking Off the Halloween Season
Today officially marks the start of the Halloween season, and the world around you will prove it. Stores are fully stocked, porch lights will start glowing orange, and spooky playlists are creeping back onto your speakers.
And if you need one more nudge: Freeform’s 31 Nights of Halloween kicks off tonight. That’s right — a whole month of Halloween classics playing in the background while you decorate, plan, and snack on too much candy corn.
📝 Build Your October Halloween Bucket List
Part of the fun of the Halloween season is having little moments to look forward to all month long. A simple family bucket list can help you make memories without feeling like you have to “do it all.” Here are some easy, fun ideas to get you started:
- Decorate your porch with pumpkins, cobwebs, or spooky lights.
- Carve pumpkins (or paint them if you want a less-messy option).
- Have a Halloween movie night — Hocus Pocus, anyone?
- Bake something festive like pumpkin bread, spider cookies, or caramel apples.
- Visit a pumpkin patch or local farm stand.
- Check out a haunted house (or make a kid-friendly “haunted hallway” at home).
- Dress up for a family costume photo — even if it’s silly, it makes a fun memory.
- Host a spooky game night with themed snacks.
- Do a Halloween craft — paper bats, ghost garlands, or painted rocks.
- Make s’mores around a firepit (bonus if you tell ghost stories).
- Go on a Halloween lights walk to see neighborhood decorations.
- Try a seasonal drink at home like pumpkin spice lattes or apple cider.
Pro tip: write your list on a big sheet of paper and hang it where everyone can see it — that way you’ll actually check things off instead of letting October slip by.
🚀 From Here On, It Moves Fast
The Halloween season is really the starting line of the holiday marathon. Once October begins, things start to snowball quickly:
- School activities and fall festivals
- Halloween parties and trick-or-treating
- Thanksgiving prep (menus, travel, and shopping lists)
- Christmas shopping, decorating, and traditions hot on its heels
That’s why this September check-in matters so much. By pausing now to reflect on what’s done and carrying unfinished items forward, you’ll avoid the frantic catch-up that tends to sneak in by mid-October.
✨ Pro tip: Go ahead and buy your Halloween candy this week. And if your house is like mine, grab an extra bag just for the family so the trick-or-treat stash actually makes it to October 31.
Think of this as the calm before the storm — but a fun storm, filled with cozy vibes, spooky fun, and family memories.
🗒️ Today’s To-Do List
Here’s what to focus on today to kick off the Halloween season feeling prepared:
- Review your September calendar → circle what’s done, star what’s unfinished.
- Carry any leftover September tasks into October.
- Start your Halloween bucket list with 2–3 fun activities for the month.
- Buy your Halloween candy (and a spare bag for the family stash).
- Put on Freeform’s 31 Nights of Halloween to set the mood.
