Autumn has officially started, which means the busiest stretch of the year for most online stores is about ten weeks away. The stores that do well in November and December usually aren’t the ones with the cleverest offers. They’re the ones that decided early what they’d send, when, and to whom.

This calendar lays out the 2025 holiday season week by week, with the key dates, what to prepare, and when each email should go out. Adapt it to your products and your market, but use it as a skeleton so nothing lands at the last minute.

The key dates for 2025

Here are the dates most WooCommerce stores plan around this year:

Because Thanksgiving falls late this year, the gap between Black Friday and Christmas is shorter than usual. That makes shipping cutoffs and email timing more important, not less.

Late September: plan and set up

This is the time for decisions, not sends.

• Pick your offers. Decide what you’ll run for Black Friday and Cyber Monday, and whether you’ll do an early-access sale for subscribers. Work out the margin on each offer before you commit.
• Check stock. Look at last year’s bestsellers and anything that’s trending now. Reorder early; supplier lead times usually get longer in Q4.
• Confirm carriers’ holiday deadlines as soon as they’re published and write them into this calendar.
• Clean your email list. Remove hard bounces and long-inactive addresses. Sending big campaigns to a dirty list is one of the fastest ways to end up in spam. Our guide on why WooCommerce emails go to spam covers the technical basics.
• Check authentication. Since Gmail and Yahoo introduced stricter bulk sender requirements in 2024, SPF, DKIM, DMARC and one-click unsubscribe have been essential for anyone sending marketing email at volume.

Early October: build your list and your segments

The more subscribers you have before Black Friday, the more of your sales you’ll make from owned channels instead of ads.

• Launch a holiday list-building popup. An “early access to Black Friday” offer works well because it costs you nothing until the sale.
• Set up your segments. At minimum: past buyers, subscribers who’ve never bought, VIPs or repeat customers, and lapsed customers who haven’t ordered in a year or more.
• Build your templates. Design a Black Friday template, a Cyber Monday template and a gift guide template now, while you have time to test them on mobile.
• Plan a gift guide. Group products by recipient (“for her”, “for the host”, “under 25”) or by price band. Gift guides are useful content for both email and your site.

Mid to late October: warm up

• Send your gift guide in the second half of October. Early shoppers are already looking, and it’s a useful send that isn’t a discount.
• Halloween campaign if it fits your products, going out a week or so before 31 October.
• Tease Black Friday. Tell subscribers something is coming and that they’ll get it first. This also nudges people to join the list.
• Increase sending gradually if your list is large and you’ve been sending rarely. A sudden jump from one email a month to one a day can hurt deliverability.

Early November: final preparation

• Singles’ Day, 11 November. A useful test run for your sale mechanics: coupons, landing page, checkout, emails.
• Build your Black Friday landing page and test it on a phone.
• Load-test the site or at least check that your hosting can cope with a traffic spike. Talk to your host about expected peaks.
• Schedule your emails. Aim to have every Black Friday week email written and scheduled by mid-November.
• Set up automations that matter most in busy weeks: abandoned cart, browse follow-ups and a post-purchase thank-you. If you need a refresher on abandoned cart emails, see the art and science of cart abandonment emails.

Black Friday week: 24 November to 1 December

A simple email schedule for a small store might look like this:

1. Monday 24 Nov: Early access for subscribers or VIPs.
2. Thursday 27 Nov (evening): “Starts tomorrow” reminder, or the sale opens early for the list.
3. Friday 28 Nov (morning): Black Friday launch to the full list.
4. Saturday 29 Nov: A Small Business Saturday angle, or a reminder to people who opened but didn’t click.
5. Sunday 30 Nov: Best sellers, “still available” message.
6. Monday 1 Dec (morning): Cyber Monday offer.
7. Monday 1 Dec (evening): “Last hours” reminder to non-buyers only.

Exclude people who’ve already bought from the reminder emails. Nothing annoys a new customer faster than being told to hurry up and buy something they bought yesterday.

Early to mid December: gifting and shipping deadlines

After Cyber Monday, the message shifts from “deals” to “gifts that arrive in time”.

• Giving Tuesday, 2 December. If you support a cause, this is the day to say so. Keep it genuine.
• Green Monday, 8 December. A good day for a second push to people who didn’t buy during Black Friday week.
• Shipping cutoff reminders. Send one about a week before your last standard shipping date and one a day or two before it. Put the date in the subject line.
• Gift cards once physical shipping deadlines have passed. They’re the answer for last-minute shoppers.
• Click-and-collect or local pickup if you offer it, as a late option for local customers.

Christmas week and after

• 24 to 25 December: Most stores go quiet. A short thank-you or holiday greeting works; a hard sell usually doesn’t.
• 26 December: Boxing Day sale if it’s a big day in your market, or a “treat yourself” message aimed at people who received gift cards.
• Late December: Post-purchase emails to new customers, asking for reviews and suggesting related products.
• Early January: Returns and exchange questions will come in. Make your returns policy easy to find, and consider offering an exchange or store credit instead of a refund where that fits.

A worked example: a small candle shop

Imagine a WooCommerce candle shop with around 2,000 subscribers (a hypothetical figure). Here’s how the plan might look in practice:

• Late September: Orders extra stock of its two bestselling scents. Cleans the list and removes addresses that haven’t opened anything in over a year.
• Early October: Runs an “early access to our Black Friday bundles” popup. Sets up four segments: buyers, non-buyers, repeat buyers and lapsed.
• Late October: Sends a gift guide split into “under 20”, “for the host” and “self-care sets”.
• Black Friday week: Sends seven emails as above, with reminders only to people who haven’t bought.
• Early December: Sends shipping-deadline reminders, then switches to gift cards after the last shipping date.
• January: Sends a “how to get the most from your candle” email to new customers, followed by a review request.

None of this is complicated. What makes it work is that every step was decided in September.

Tools that make this easier

You can run this plan with almost any email platform that supports segments and scheduled sends. The important features are segmentation by purchase history, automations for carts and post-purchase follow-up, and templates you can reuse through the season.

iConvert Email Marketer segments WooCommerce customers automatically and comes with pre-designed templates, which saves time when you’re preparing a dozen seasonal emails at once. If you want a broader look at how email fits with your other tools, our overview of CRM, email marketing and marketing automation is a good starting point.

Your next step this week

Print this calendar or copy it into your planning tool, then fill in three things today: your Black Friday offer, your carriers’ last shipping dates, and the date your first holiday email goes out. Everything else in the season hangs off those three decisions.

If you want your holiday segments and templates ready before October, iConvert Email Marketer can take care of the setup work for you.