Here is the truth about holiday marketing: most small businesses wing it. They remember Valentine's Day a week before, scramble for Black Friday the Monday prior, and completely forget about Small Business Saturday until they see it on the news. Then they wonder why their campaigns fall flat.
You are not going to do that this year. And honestly, you do not have to — tools like Cherub Email track the calendar for you and send proactive reminders with pre-written campaigns ready to approve. But whether you use a tool or a spreadsheet, the important thing is knowing what is coming and when.
The holiday season from November through December alone accounts for up to 50% of annual sales for some retail businesses. The 2025 holiday season topped $1 trillion in consumer spending in the US. And it is not just Q4 — Valentine's Day hit a record $29.1 billion in 2026, Mother's Day reached $34.1 billion, and Small Business Saturday drove $17 billion back in 2023 (and it has only grown since).
This calendar covers every date worth knowing, the spending data behind it, how far ahead to start planning, and what to actually send. Bookmark it. Reference it quarterly. Your future self will thank you.
Q1: January – March
Fresh starts and the first big spending holiday
New Year & Resolution Season (January)
January is the month of optimism. Gyms see a 25% or greater increase in new memberships. Health food stores, wellness studios, organizing services, and self-improvement businesses all ride this wave. But it is not limited to fitness — any business that can tie into a "fresh start" angle has an opening here.
The key is timing. Send your first campaign the first week of January while the motivation is high. Frame it around helping customers keep their resolutions, not guilting them into purchases. A coffee shop can promote a new healthy menu. A salon can pitch a "new year, new look" package. A bookshop can curate a self-improvement reading list. The angle works because it is genuinely useful.
Valentine's Day — February 14 (Saturday)
Valentine's Day 2026 hits a record $29.1 billion in total spending, with the average person dropping $185.81. The Saturday landing is a gift for your business — it means dinner reservations, daytime shopping trips, and couples outings are all on the table.
Here is what makes Valentine's Day interesting for planning: 52% of shoppers plan their purchases in advance. That means your email needs to land well before February 14. Start your campaign sequence in early January, about 6 to 8 weeks before the day. And note that 41% of Valentine's spending goes to restaurants, making it the single biggest dining holiday of the year. Salons, florists, and boutiques round out the top categories.
For your emails, skip the generic "treat your sweetheart" language. Get specific. If you are a restaurant, promote your Valentine's prix fixe menu with an early-bird booking discount. If you sell retail, curate a gift guide at different price points. Make it easy for people to say yes.
Presidents' Day — February 16
Presidents' Day has become a reliable sales event, especially for retail. It is a long weekend and people are shopping. You do not need a complex strategy — a straightforward weekend sale with a clear deadline works. One email the Thursday before and one on Saturday morning. Keep it simple.
St. Patrick's Day — March 17
St. Patrick's Day is lighter on spending but high on foot traffic for restaurants, bars, and bakeries. Green-themed specials, limited-time menu items, and event promotions all perform well. Two to three weeks of lead time is plenty. A single email the week before with a reminder on the day itself is the right cadence.
Cherub handles this for you: For major Q1 holidays like Valentine's Day, Cherub sends you reminders at 14, 7, 3, and 1 day before the date — each with AI-written campaign copy tailored to your business. You just review and approve. No spreadsheet required.
Q2: April – June
The two biggest gifting holidays of the year
Easter — April 5
Easter drives solid spending for bakeries, florists, restaurants (brunch is huge), and retail. Families gather, which means group dining and gift-giving. Start your campaign about three weeks out — an early-bird brunch reservation email in mid-March, followed by a reminder the week before Easter with any special hours or menus.
Mother's Day — May 10
Mother's Day is a powerhouse: $34.1 billion in total spending, making it one of the highest-spending holidays of the year. If you run a salon, restaurant, florist, or boutique, this is your Super Bowl.
Lead time matters here. Start your campaigns in early April, a full 6 to 8 weeks before the day. Shoppers are planning ahead and your email needs to be in their inbox when they are deciding where to book and what to buy. Gift cards, experience packages, and pre-booked appointments all convert well. Be direct about what you offer and why it makes a great gift — do not make people guess.
Memorial Day — May 25
Another long weekend, another reliable sales opportunity. Memorial Day kicks off summer, which means seasonal promotions, new summer menus, extended hours, and outdoor events all work as campaign angles. One week of lead time is enough. Keep the tone celebratory and the offer clear.
Juneteenth — June 19
Juneteenth is a growing commercial holiday, now a federal holiday since 2021. Restaurants, event venues, and retail stores can run celebration-focused promotions. The key here is authenticity — celebrate genuinely, support the community, and avoid anything that feels like you are co-opting the holiday to push product. A well-timed email highlighting special events, menu items, or community partnerships is the right approach.
Father's Day — June 21
Father's Day spending does not match Mother's Day, but it is still substantial and growing. Restaurants, sporting goods, grooming shops, and experience-based businesses do well here. Start your campaign in early May, about 6 weeks out. Gift guides and pre-booked experiences convert better than generic "Happy Father's Day" emails.
Graduation Season (May – June)
Graduation is not a single day but a two-month window of spending. Salons book out with grad party prep. Boutiques sell celebration outfits. Restaurants host graduation dinners. Bakeries make custom cakes. If any of this applies to you, start promoting in mid-April and keep it going through June. A "book early" angle works well since popular time slots fill fast.
Cherub handles this for you: Q2 is packed with big holidays. Cherub starts creating campaign suggestions 30 days ahead of each one, then reminds you at the right intervals with ready-to-send copy. Mother's Day, Father's Day, Easter — they all show up in your dashboard before you have to think about them.
Q3: July – September
Summer peaks and the back-to-school rush
Independence Day — July 4 (Saturday)
The Fourth of July lands on a Saturday in 2026, which is ideal for food businesses, outdoor venues, and anyone who benefits from long-weekend foot traffic. BBQ specials, patriotic-themed products, and event promotions all work. Start promoting about two weeks out. If you are a restaurant or food business, push pre-orders for catering and party platters — those decisions get made early.
Back-to-School (August)
Back-to-school is a retail juggernaut, but it extends beyond school supplies. Salons do back-to-school haircuts. Restaurants near schools and campuses see traffic shifts. Gyms promote fall fitness routines. If your customer base includes families, August is when they are spending. Launch your campaigns in late July with a focus on convenience and value.
Labor Day — September 7
Labor Day marks the unofficial end of summer and the last big weekend before the holiday season planning begins. End-of-summer sales, fall menu launches, and new-season promotions all fit naturally. One email the week before with a "last chance for summer" angle tends to perform well.
National Coffee Day — September 29
If you are a cafe or coffee shop, this is your day. Free drink promotions, loyalty bonuses, and limited-time seasonal drinks (hello, fall menu) drive real foot traffic. But even non-coffee businesses can play — a "grab a coffee on us" gift card giveaway or a cozy fall-themed campaign works if your brand fits the vibe. Minimal lead time needed, just a week or so.
Cherub handles this for you: Cherub also watches the weather. If a heat wave or cold snap hits your area, you will get a campaign suggestion automatically — "Beat the heat with iced drinks" or "Warm up with us" — no calendar entry needed. These real-time triggers sit alongside the holiday reminders so nothing slips through.
Q4: October – December
The big one. Up to 50% of annual revenue for some businesses.
If you only plan ahead for one quarter, make it this one. Q4 is where the money is — and where poor planning costs you the most. Start your Q4 planning in September, a full 8 to 10 weeks before Black Friday. That sounds early. It is not. By the time October hits, your competitors are already in inboxes.
Halloween — October 31 (Saturday)
Halloween on a Saturday means big events, big foot traffic, and big spending. Bakeries, restaurants, salons (costume-ready hair and makeup), and retail all benefit. Themed promotions, limited-edition products, and event tie-ins work well. Start your Halloween campaign in early October — enough time for people to plan their celebrations and costumes, but not so early that it feels premature.
Small Business Saturday — November 29
This one is personal. In 2025, 63 million Americans shopped in-store on Small Business Saturday. The day generated $17 billion in spending back in 2023, and the number has climbed since. For some small businesses, this single day accounts for up to 20% of their yearly revenue.
Here is the important stat: 88% of shoppers say they prefer to receive offers before the holiday. That means your Small Business Saturday campaign should start in October, not the week of Thanksgiving. Build anticipation. Give people a reason to put your shop on their list. Exclusive in-store offers, early access for email subscribers, and "bring a friend" promotions all perform well.
Your email sequence should look something like this: a "save the date" in early November, a preview of your offers the week before, and a reminder on the morning of. If you do SMS too, a morning-of text with your best offer is gold.
Black Friday — November 27
Black Friday is two days before Small Business Saturday, which means the whole weekend becomes a shopping event. Your Black Friday email should land the week before and focus on your strongest offer. Do not try to compete with big box stores on price — compete on experience, curation, and the personal touch that only a small business provides. "Shop local this Black Friday" is a powerful message when it is backed by a genuinely good offer.
Cyber Monday — December 1
If you have any online presence at all — gift cards, online ordering, e-commerce — Cyber Monday is worth a dedicated email. Even purely brick-and-mortar businesses can sell gift cards online. It extends the Thanksgiving weekend momentum by one more day and catches the people who were not ready to buy over the weekend.
Christmas & Holiday Season — December 25
The holiday season is a marathon, not a sprint. Your December email strategy should balance promotion with warmth. Early December is for gift guides and holiday specials. Mid-December is for last-minute shoppers (gift cards, experience packages, anything that does not require shipping). The week before Christmas is for holiday hours, last-chance reminders, and genuine gratitude for your customers' support throughout the year.
Do not neglect the period between Christmas and New Year's. Gift card redemptions, post-holiday sales, and "treat yourself" campaigns catch people who are off work, have gift money to spend, and are in a shopping mood.
Industry Cheat Sheet
Not every holiday matters equally for every business. Here are the dates that move the needle the most for each industry. Focus your energy where the data says it counts.
| Industry | Top Holidays (in order) | Why |
|---|---|---|
| Restaurants | Mother's Day, Valentine's, Father's Day, Easter, NYE | 41% of Valentine's spend goes to dining. Mother's Day is #1 for reservations. |
| Salons | Mother's Day, Valentine's, New Year, Grad Season, Wedding Season | Gift cards + "get ready" appointments drive bookings all year. |
| Retail | Black Friday, Small Biz Saturday, Cyber Monday, Valentine's, Mother's Day | Q4 alone can be 50% of revenue. 63M shopped Small Biz Saturday in 2025. |
| Florists | Valentine's, Mother's Day, Christmas, Easter | Valentine's = 30% of annual sales. Mother's Day = 28%. Two days, 58% of revenue. |
| Gyms | New Year, Spring, September, Beach Season (May-June) | 25%+ membership spike in January. Second wave in spring/beach season. |
| Cafes | National Coffee Day, Fall Season, Holiday Season, Back-to-School | Seasonal drink launches drive repeat visits. Fall is the biggest window. |
How Far Ahead to Start
The number one mistake in holiday marketing is starting too late. Here is your cheat sheet for lead times. Pin this somewhere visible.
| Holiday | Date (2026) | Start Planning | First Email |
|---|---|---|---|
| New Year | Jan 1 | Mid-December | Dec 28 – Jan 2 |
| Valentine's Day | Feb 14 | Early January | Jan 12 – 19 |
| Easter | Apr 5 | Early March | Mar 16 – 23 |
| Mother's Day | May 10 | Early April | Apr 13 – 20 |
| Father's Day | Jun 21 | Early May | May 11 – 18 |
| Independence Day | Jul 4 | Mid-June | Jun 22 – 29 |
| Halloween | Oct 31 | Early October | Oct 5 – 12 |
| Black Friday | Nov 27 | Late September | Nov 3 – 10 |
| Small Biz Saturday | Nov 29 | October | Nov 3 – 10 |
| Christmas | Dec 25 | Late September | Nov 24 – Dec 1 |
Frequently Asked Questions
How far in advance should I plan holiday marketing campaigns?
It depends on the holiday. Major shopping holidays like Black Friday and Christmas need 8 to 10 weeks of lead time — start planning in September. Valentine's Day and Mother's Day need 6 to 8 weeks. Smaller holidays like St. Patrick's Day or National Coffee Day only need 2 to 3 weeks. The key rule: 88% of shoppers prefer receiving offers before the holiday, so earlier is almost always better than later.
Which holidays matter most for small businesses?
The top revenue drivers for most small businesses are the Q4 holiday season (Black Friday through Christmas), Valentine's Day ($29.1B in spending), Mother's Day ($34.1B in spending), and Small Business Saturday ($17B in 2023). But the best holidays for your specific business depend on your industry. Restaurants peak on Valentine's Day and Mother's Day. Florists get 30% of annual revenue from Valentine's Day alone. Gyms see their biggest spike in January. Check the Industry Cheat Sheet above to find your top dates.
How many holiday marketing emails should I send?
For major holidays, plan a 3-email sequence: an early announcement (2 to 3 weeks out), a reminder with specific offers (1 week out), and a last-chance email (1 to 2 days before). For smaller holidays, a single well-timed email is enough. The goal is to be helpful, not to flood inboxes. If your offer is genuinely useful, people want to hear about it.
What if my business doesn't fit traditional holiday categories?
Every business can find relevant moments in the calendar. The trick is to think about what your customers are doing around each holiday, not whether the holiday directly relates to your products. A gym can run a "recover from Thanksgiving" campaign. A bookshop can do Valentine's Day gift guides. A pet groomer can offer holiday photo packages before Christmas. Start with 4 to 5 holidays that feel natural for your business and expand from there.