Holiday Planning in October How To: 5 Do-Ahead Steps

The holiday season may seem distant to you, even out of focus. But as we’ve all experienced, once it hits, this distant vision can quickly become a blur. Sure, I picture lit candles, festive foods, friends and family, and relaxation. But often, the reality of these four or five weeks is anything but. Menus to plan, gifts to buy and wrap, events to host and attend. Tackling 5 key do-ahead steps to holiday planning can mean a much more enjoyable, less frenzied holiday season.

This October, I’m taking the approach I wish I’d taken years ago. I’m getting ahead of the holidays with small, manageable steps. Not frantic, not overachieving, just wise preparation that frees up time and sanity when it matters most. Here are five things I’m doing now that I know my December-self will thank me for.

1. Taking stock of my holiday decor (and doing a gentle purge)

One of the fastest ways to make December easier is to know what you actually have. Decorations multiply over time. Think candles tucked in boxes, garlands that have lost their sparkle, ornaments whose hooks have mysteriously disappeared. Every year I promise myself I’ll sort through it “after the holidays,” but by January, I’m too tired to care. Instead of purging, everything gets stuffed into the bin it came from. So this year, I’m doing it now.

In early October, I pull out my bins and boxes, and spread it all out. I take a quiet Saturday morning, make a pot of coffee, and treat it like a treasure hunt. What do I truly love? If you’ve moved you’ll probably find the garland that perfectly encircled your staircase has no place to go in your new place. Maybe it’s just the sheer volume of decorations that’s overwhelming you and your storage space.

Decluttering now means I’ll decorate faster and more joyfully later. I’ve learned that less really is more. Fewer decorations, but the right ones, make the whole home feel peaceful instead of chaotic. For me, that’s the Santa pillow my grandma sewed together and stuffed decades ago. And the spinning musical Santa, rotating to the sounds of ‘Santa Claus is Coming to Town.’ I also jot a quick list of what needs replacing, like a string of lights or a missing wreath hook. I still vividly remember during Covid being unable, at any cost, to purchase tinsel for our tree. There simply was none. So order what you need, now, while supplies are fully stocked.

This kind of holiday planning means that by Halloween, everything’s neatly packed and labeled again. I’m definitely not an early-decorator. Nothing comes out for the season until after Thanksgiving. But when it’s time, I know exactly where my favorite pieces are.

When our kids were young, we’d pick a day after school to start decorating. They all loved helping and while decorating isn’t quite as exciting as it once was, I put on some music, and begin. When I can do this without digging and sighing and wondering what I’m missing, this is a much more fun experience.

2. Holiday planning: Getting a head start on gifts

Few things unravel our calm faster than last-minute gift shopping. Between long lines, shipping delays, and trying to guess what people might want, the process can feel more like a marathon than a pleasure. This year, I’m easing into it early, starting in October.

My first step is simple: I make my list. Not a fancy spreadsheet—just a note on my phone or a page in my notebook. I write down everyone I plan to give to this year, then add a few ideas next to each name. I don’t need the perfect idea for everyone right away. Just a direction.

October is a great time for holiday planning because sales quietly start before the big holiday promotions hit. Retailers want to capture early shoppers, and it’s the perfect chance to pick up thoughtful gifts without the frenzy. Plus, spacing out purchases helps avoid that December financial crunch that always seems to hit when all the shipping carts fill at once.

If I’m shopping online, I check shipping times and availability now. If I’m buying locally, I make a note of the small businesses I want to support this year and plan a couple of November visits to shop when it’s still quiet.

And I’ve learned one more trick: I keep a small bin or shelf in a closet as my “holiday gift station.” As gifts arrive, they go straight there, along with gift wrap, tissue, tags, and tape. By the time December rolls around, much of my shopping is done, and all I need to do is wrap and enjoy the process.

Starting gifts early isn’t just practical, it changes the emotional tone of the holidays. It allows time for real thoughtfulness. For me, it’s less about checking boxes and more about finding things that will truly delight the people I love. Holiday planning at its finest.

3. Holiday menu plans and prep (yes, in October)

It might sound early to think about holiday meals, but food is the heart of so many gatherings, and it’s also one of the biggest stressors. Every year I find myself running to the store for last-minute ingredients, or worse, realizing I’m out of the one spice I need for a favorite recipe.

So this October, I’m taking a more intentional approach. I start by jotting down the meals I’ll likely host or contribute to, like Thanksgiving dinner, a December brunch, Christmas Eve appetizers, a New Year’s Eve dish. I’m not setting anything in stone, but just sketching a loose outline of what’s coming.

Once I have that list, I pull out my favorite recipes and check what I already have in the pantry. It’s a great time to restock the staples like flour, sugar, baking powder, spices, nuts, canned pumpkin, chicken broth. Most of these ingredients are shelf-stable and easy to tuck away now.

By doing this early, I save money (before prices spike closer to the holidays) and avoid the stress of crowded stores. I even prep a few make-ahead items, like homemade cranberry sauce or cookie dough that freezes beautifully. For me, I begin baking Biscotti in late October, so it’s ready to go from Thanksgiving through New Year’s.

I also make it a priority in late October to purge my freezers. Anything that’s freezer burned, unrecognizable or just plain unappetizing, goes. I need space for not only holiday meals, but also Biscotti and Christmas Cookies that I want to make ahead and keep fresh.

Another bonus: by planning menus now, I can start looking for serving dishes, utensils, or table décor that I might need, before everything’s picked over. If I know I’ll need extra wine glasses or a certain baking dish, I order them now and tuck them away.

A friend of mine starts a “Holiday Freezer List” every October, just a sticky note on her freezer door that lists what’s prepped and ready. I’m borrowing that idea this year. By December, the goal is to have a few things waiting, a plan in place, and the peace of mind that comes from knowing dinner doesn’t depend on a last-minute grocery miracle.

4. Scheduling the holidays before they schedule me

The holiday season has a sneaky way of filling itself with parties, concerts, gatherings, errands. In the past few years I’ve noticed anyone I haven’t seen in a while absolutely positively feels the need to ‘get together’ before the holidays. Great though this may be, it can also be stressful. If you went to their house last year, that means I’m up this year.

By the time December arrives, it can feel like we’re living someone else’s calendar. This year, I’m trying something new: I’m setting the tone and pace of the holidays before they overtake me. Living with intention always feels better.

That starts with my calendar, both paper or digital, since paper works better for things like menus and baking. Digital works better for gift lists because I can easily add links to things I’m considering. In early October, I start plugging in the big events I already know about: friend dinners, kids’ breaks and travel schedules, and any larger family gatherings. Then I block off a few “white space” weekends, days I intentionally keep free so I can rest, bake cookies, or just enjoy the season without rushing.

I also use this time to book appointments that tend to fill up quickly: salon visits, or home cleanings before kids or guests arrive. October is early enough that schedules are still open, and booking now means one less scramble later.

The other part of planning is emotional: deciding what kind of December I actually want. Do I crave quiet evenings with lights and music, or am I energized by gatherings and outings? The answer may be somewhere in the middle, for us. Knowing that helps me say yes, or no, with confidence as invitations start rolling in.

I’ve learned that the calmest Decembers don’t happen by accident. They’re built with intention, one early decision at a time. The reward? More moments that feel meaningful, and fewer that feel like obligations.

5. Ordering holiday cards (and gathering addresses) early

Every year, holiday cards used to sneak up on me. I loved sending them but they were a mini-marathon to get out. The outfits for the kids, the photo shoot(s), the photo editing, the card design. The process always seemed to land right when everything else peaked. We only send holiday cards every few years now. My goal is to keep in touch with those I’d send cards to on a more regular basis. Not just the once-a-year stock family update. But there’s a time and place for every approach to cards.

My suggestion is that October is the month to make it easy, if you plan to send holiday cards. Start by updating your address list. A quick text or email to friends helps confirm new addresses before the holiday rush.

Then, decide what type of card you want: photo cards, classic designs, or something handmade, and order them now while discounts are plentiful. Printers are faster in October, too, and you can take your time writing personal notes without rushing.

For those who send cards digitally, it’s still worth setting up the list early. Draft your message, choose a design, and schedule the send. A little organization now turns what’s often a stressful December chore into something lovely and even meaningful.

I also use this step as a prompt to refresh my wrapping supplies: tape, tags, ribbon, and paper. These are easy to forget until it’s midnight and you’re out of tape. By restocking now, I know I’m set for those spontaneous wrapping sessions or when the kids get home, armed with gifts, all requiring wrap and ribbon.

Why October is the month to begin holiday planning

The beauty of doing these things in October isn’t just that December feels lighter, it’s that November and December become more fun. The season unfolds instead of unravels. There’s time for spontaneity because the essentials are already handled.

I think many of us reach midlife realizing that our peace of mind matters as much as any tradition we uphold. We’ve hosted, baked, shopped, and stayed up late making everything magical for everyone else. But this stage of life offers a different kind of wisdom. We now understand that joy and ease are worth planning for, too.

So, this October, I’m giving myself the gift of time. A few small, thoughtful steps now, organizing decorations, mapping menus, scheduling ahead, will make December feel calmer, cozier, and more meaningful. It’s not about perfection; it’s about presence.

And the more we prepare with intention, the more we can simply live the moments when they arrive. Then we can sit in the glow of the tree, knowing we did it right this time.

Closing reflection: Making space for joy

If you’re reading this and already feeling behind, don’t. The point isn’t to do everything perfectly or early. It’s to remember that peace of mind is built in layers, and October offers us the perfect layer of calm before the cheer.

Maybe you start with one thing, like sorting your decorations or planning your holiday cards, and let the rest unfold from there. The smallest early efforts often make the biggest difference later.

Because December doesn’t have to be chaos. It can be beautiful, simple, and bright. And that begins now, in October, with a cup of coffee, a good list, and the comforting promise that we’re creating a holiday season we’ll actually have time to enjoy.