It’s that time of year… to slowly start thinking about the holidays. While I am already in full holiday mode, I in no way expect everyone else to be. (And the blog will be normal topics aside from a post here and there until mid-November!) However, one thing that comes up a lot with friends, family, and readers alike- how do I get prepared for the holidays? When do you typically need to do things to have them done in time? I’ve got a basic checklist of what needs to be done when (for a normal person, not a holiday enthusiast like myself). So, here is my Christmas preparation timeline, to help you tackle everything in time and avoid holiday stress!

There are several lists out there on the internet, but a lot of them were written pre-Covid when shipping times were much faster, and for an American audience only sending things/staying in the US. This is for everyone, everywhere!
This list isn’t meant to turn you into someone like me who is already watching Christmas music and listening to my playlists, but to help things go smoothly in November and December so that you can actually enjoy the season instead of rushing around and worrying about what needs doing.
Christmas Preparation Timeline

September
We are still fairly far away from the holiday season at this point, so not much needs to happen right now but a handful of key things can help.

Set Your Holiday Budget
Before we get into the true swing of things, set your holiday budget now. Of course we all factor in gifts and food, but also think of any travel costs (car rentals, gas, hotel rooms, plane tickets). Host/ess gifts often get forgotten but then many of us spend a ton last minute, so plan for some of these as well. Christmas cards and any mailing costs- mailing Christmas cards or Christmas gifts can also add a LOT to your budget quickly. And of course, any donations that you would like to make. Once you have your budget, you can figure out how much you can set aside/handle on each pay cheque to spread it out.

Christmas Card Photos/Ordering
If you get photos taken for your holiday cards, now is the time to do it. Photographers are incredibly busy at this time of year (and fall weddings are even more common now as people rebook cancelled weddings), and they need time for editing.
I know a lot of people who order their cards on Black Friday in the US, and send them out in December, but if you send your Christmas cards internationally (especially in the time of Covid), you typically need to mail them out by mid-November to guarantee delivery. I would recommend ordering your cards (or purchasing by the end of September) to have them done in time to send out.

Start Buying Gifts
If you see gifts on sale or in a deal (that actually does save you money), buy them now and put them aside. You have to start thinking about it earlier, but you can save a great deal, and with shipping times still quite long (and predicted to get longer at the holidays again), it’s best to get organised early. Also, if you like supporting small businesses, remember that they will often have holiday deadlines that are much earlier.

Get Your Advent Calendar Ordered
If you are particular about your Advent Calendar, get it ordered now. Many are going up for pre-order in August and September and selling out in days or weeks. If you like something fancier than your standard chocolate calendar, order ahead!

October
If you are in Canada, we have Thanksgiving on the second Monday of October, a nice turkey-based holiday to get you in the mood. If you aren’t you’ve still got trick-or-treating and Halloween to round out the month! You can also get started on a few more things to make the holidays go a little smoother.

Get Started on DIY Gifts
If you are planning on making some or all of your gifts, definitely get started making them earlier rather than later. (A lot of crafters I know plug away at gifts throughout the year, and there is nothing wrong with that at all!) You never know if you are going to have change one of your ideas, or get sick or busy with unplanned work, and it’s better to have them finished earlier rather than later.

Choose Holiday Event Dates
If you can/ feel comfortable hosting a holiday event, pick your date earlier rather than later. I would have tentative dates picked by the end of October. A lot of holiday parties start in mid-November for workplaces and organisations, and mid-November through the end of the year can be hectic. Get your dates in the calendar so people can plan! (The details can definitely wait, just get your date set.)

Mail International Christmas Cards and Gifts
Check with your postal service for international mailing gifts for cards and gifts, and get those out on time. A late gift or card isn’t the end of the world, but can also be avoided with a little planning. I know that mailing from Canada to New Zealand/ Australia often has a recommended deadline of October 15th, and Europe is often in the first week of November- don’t let them sneak up on you.

November
November marks several holidays. November 11th is Remembrance Day in Canada and Armistice Day in the UK, Remembrance Sunday is the second Sunday in the UK, and Thanksgiving is the last Thursday in November in the US. Life is getting busier (and darker) by November, and there can be a lot to keep track of.

Mail Domestic Christmas Cards and Gifts
Aim to have everything mailed out domestically by the end of November. (I have to say, I love putting up Christmas cards at home, but they get taken down right after New Year’s Eve- let us see them longer!) Again, with Covid and various supply chain issues, don’t leave this to the last minute.

Try New Recipes
If you want to try any new recipes, try them in November. If they don’t go the way that you expect, or you don’t think that they will work for what you need, don’t be afraid to try something else. Speaking from personal experience, if you wait until the day before your holiday party or potluck to try a new recipe, you might be in for a lot of frustration and rage. Throw on one of your favourite movies and try to make a half-batch as a trial!

Get Your Advent Calendar
If you don’t already have your Advent calendar, grab it in mid-November. I’ve noticed here that stores get largely cleared out in the 3rd and 4th week. (“Buy your Advent calendar on clearance in the middle of December” is a common money-saving tip I’ve seen; however, I’ve not seen many that last that long.)

Buy Your Baking/Gift Wrapping Supplies
If you give out baking as gifts, make sure you buy all wrapping supplies early. In early November 2020, you could only buy essential items in-person, and Christmas and holiday bags and containers weren’t on that list. (Sad face but I understood…) While I was able to grab them in the week before by total fluke, I know a lot of people who missed out. (Yes, you can give out baking in normal packaging, but some of us just like themed wrapping, okay?) I then stocked up in January when stores opened up again, but I’m still missing a few things- get it ahead of time.

Plan Your Holiday Events
Now is the time to plan your holiday party- I would choose your party type and menu three weeks prior. If it is going to be a potluck, tell people as early as possible. (Give some sort of direction on what people should bring, or have a sign up sheet. Some people enjoy making or bringing whatever, but some people find it stressful to have no guidelines.) And if you want people to wear something specific, tell them ahead of time but also understand that people might not be able to match the dress code completely. (Holiday parties should be fun!)

December
December is the thick of it- Hanukkah, Christmas, Kwanzaa, and more. Holiday parties, concerts, The Nutcracker, it’s a busy time. But hopefully there isn’t much left to do but enjoy!

Make Donations
If you haven’t already made your holiday donations, do this in the first week of December. If you donate items to something like the Shoebox Project or something given as a gift, it will most likely have a deadline in the first weekend. While other organisations like food banks and charity support orgs obviously always welcome donations, if they do something particular for the holidays- ie. separate hampers, a bigger meal for clients- it makes their planning much easier to know what their budget and/or inventory is.

Plan Your Holiday Meal
If you host a holiday meal (even a solo meal), plan it out ahead. If you do have the traditional turkey or roast, start looking in the beginning of December to catch a sale. Also, buy things like cranberry sauce ahead of time- we all have forgotten it several times when it could be bought far ahead.

Do Your Holiday Traditions
If you always go to The Nutcracker or drive around looking at Christmas lights or have a movie marathon, do it. These things often get lost in the shuffle, but the holidays should be fun and enjoyable- do the things you love!
♠
I hope that this Christmas preparation timeline can help make your holiday season go a bit more smoothly, and that you can avoid as much frustration as possible! With a bit of time
Cheers,
The Historian
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