Best Shop Holiday Deals and Discounts

Shop Holidays

Shopping holidays have gotten complicated with all the sales events flying around. I remember a few years back when Black Friday was basically the only big deal day on the calendar. Now? There’s a shopping “holiday” for practically every month of the year, and honestly, it can be tough to keep track of which ones actually matter. So let me walk you through the ones worth paying attention to — and a few you might not have heard of yet.

Black Friday

Black Friday is the granddaddy of shopping holidays. It falls right after Thanksgiving and basically kicks off the whole holiday shopping frenzy. Retailers go all-out with doorbuster deals, stores open at weird hours (sometimes even Thanksgiving night), and you can score solid discounts on electronics, clothes, and home stuff.

Started in the United States
Happens on the fourth Friday in November
Known for both in-store and online sales

Here’s the thing though — Black Friday has shifted a lot in recent years. Online shopping has swallowed a huge chunk of it. A lot of retailers now start dropping deals in early November, which means the old-school chaos of people camping outside Best Buy at 3 AM has cooled down quite a bit. And then there’s Cyber Monday, which is basically Black Friday’s internet-savvy younger sibling.

Cyber Monday

Cyber Monday rolls in the Monday after Thanksgiving. It was originally created as a counterpart to Black Friday for people who preferred shopping from their couch. Can you blame them? This is where you’ll find the best deals on tech products, though clothing and accessories get marked down too.

First showed up in 2005
Heavy focus on electronics and tech
Online exclusive deals

The whole “shop from home in your pajamas” appeal makes Cyber Monday a favorite for a lot of people. Retailers have caught on and often stretch their Black Friday sales through the entire weekend into Monday. Probably should have led with this — Cyber Monday isn’t just an American thing anymore. International retailers have jumped on board with global shipping deals, and the event keeps growing every year.

Singles’ Day

If you haven’t heard of Singles’ Day, you’re missing out on what’s actually the biggest online shopping event on the planet. Yep, bigger than Black Friday. It’s celebrated on November 11th (11/11 — get it? All the ones standing alone). It started as a quirky holiday for single people in China, but Alibaba turned it into a shopping monster back in 2009.

Originated in China
Observed on November 11
Includes millions of products

The numbers from Singles’ Day are honestly mind-blowing. Flash sales, live-streamed product demos, and deals on just about everything you can think of. More international brands keep joining every year, so it’s growing way beyond its Chinese roots.

Boxing Day

Boxing Day lands on December 26th, the day after Christmas. It started in the UK as a tradition of giving gifts to service workers. These days, it’s mostly known as a post-Christmas shopping bonanza where retailers slash prices on leftover holiday inventory.

Observed in Commonwealth nations
Falls on December 26
In-store and online deals

A lot of people use Boxing Day to buy stuff they didn’t get as gifts. It’s also prime time for returning and exchanging presents that didn’t quite hit the mark. For retailers, it stretches the holiday buying season just a little bit longer, which they’re obviously not going to complain about.

Amazon Prime Day

Amazon Prime Day is a members-only event — you’ve got to have a Prime subscription to get in on the deals. Amazon launched it in 2015 to celebrate their 20th birthday, and it’s turned into a mid-year shopping event that gives Black Friday a run for its money. Deals cover pretty much everything Amazon sells.

Exclusive to Amazon Prime members
Held annually in July
Features lightning deals

Think of it as a summer Black Friday. It also drives a huge wave of new Prime sign-ups, which is obviously part of Amazon’s master plan. Their own stuff — Echo, Kindle, Fire TV — gets some of the steepest discounts. And now other retailers run competing sales during Prime Day, so everybody wins. That’s what makes Prime Day endearing to bargain hunters everywhere.

Small Business Saturday

Small Business Saturday is all about shopping local. American Express launched it in 2010 to give small, independent shops a moment in the spotlight sandwiched between Black Friday and Cyber Monday. Instead of hitting up big-box stores, the idea is to support the shops in your own neighborhood.

Celebrated on the Saturday after Thanksgiving
Focuses on local businesses
Supported by community efforts

Local advocacy groups and shop-small movements promote this day hard. It’s a nice counterbalance to the massive corporate sales. And for small businesses trying to compete during the holiday rush, the extra foot traffic really can make a meaningful difference.

Green Monday

Green Monday is one of those shopping days that kind of flies under the radar. eBay coined the term back in 2007. It falls on the second Monday in December and is basically a last-minute holiday shopping push with solid discounts across the board.

Occurs on the second Monday in December
Big sales event close to Christmas
Deals on a wide range of products

This one targets the procrastinators among us (no judgment here). With shipping deadlines closing in, there’s a real sense of urgency baked in. The deals are comparable to what you’d find on Cyber Monday, so it’s worth checking out if you’re running behind on gift shopping.

Free Shipping Day

Free Shipping Day does exactly what it sounds like. It pops up in mid-December and a bunch of retailers offer free delivery with guaranteed arrival before Christmas Eve. No minimum purchase, no coupon codes — just free shipping.

Started in 2008
Usually falls on December 14
Focuses on free delivery promotions

For anyone who hates paying for shipping (which, let’s be real, is most of us), this is a great day to knock out the rest of your holiday list. Retailers use it as one final push before the holiday shipping window slams shut.

Tax-Free Weekends

Tax-Free Weekends are a state-level thing that happens at different times throughout the year. They usually line up with back-to-school season. During these weekends, you don’t pay state sales tax on certain items like clothing, school supplies, and electronics.

Vary by state
Usually in August
Excludes sales tax on specific items

For families doing back-to-school shopping, these weekends can save you a decent chunk of money. States typically announce the dates and eligible items ahead of time, so you can plan around them if you’re organized enough.

Back-to-School Sales

Back-to-School Sales are a summer tradition at this point. They kick off around July and run through September. You’ll find deals on school supplies, clothing, laptops, and all the stuff kids (and college students) need for the new year.

Annual event during late summer
Key categories include apparel and supplies
Retailers and e-commerce sites participate

Most families time their shopping to catch these sales. Buy-one-get-one deals and bulk discounts are common. If you’ve got kids heading back to school, this is when your wallet takes the biggest hit — but at least the discounts soften things up a bit.

Summer Sales

Summer Sales happen during the warmer months and tend to focus on seasonal gear. Patio furniture, grills, swimwear, outdoor toys — all that summer stuff goes on sale. Some retailers also throw in travel deals and vacation packages.

Seasonal event during June to August
Includes outdoor and travel products
Both online and in-store deals

Retailers are really just trying to clear out summer inventory to make room for fall merchandise, so you can find some genuinely good markdowns. If you’ve been eyeing a new grill or a nice patio set, summer sales are the time to jump on it.

Winter Sales

Winter Sales start right after the holidays, usually late December into January. Retailers discount winter clothing, holiday decorations, and seasonal goods. It’s also when a ton of clearance events pop up as stores try to start the new year with clean shelves.

Starts after Christmas
Includes clearance and seasonal products
Online and physical stores participate

This is a smart time to stock up on winter coats, boots, and holiday decorations for next year. The markdowns are steep because retailers really want that inventory gone before spring rolls around.

Labor Day Sales

Labor Day Sales hit around the first Monday in September. This is one of the best times to find deals on home appliances, furniture, and mattresses in particular. It also marks the unofficial end of summer and the start of fall shopping season.

Coincides with Labor Day holiday in September
Focus on home goods and seasonal items
Both large retailers and smaller stores participate

If you’ve been thinking about a new mattress or some furniture, Labor Day is traditionally one of the best windows to buy. Retailers also use this weekend to roll out fall collections and new product lines.

Presidents’ Day Sales

Presidents’ Day Sales pop up in February around the holiday. The deals tend to focus on home goods, electronics, furniture, and sometimes automotive stuff. Travel companies get in on the action too.

Observed in February
Major focus on furniture and electronics
Participation by numerous sectors

This is another solid weekend for big-ticket purchases. The long weekend gives people extra shopping time, and retailers definitely know it — so the deals are typically worth a look.

Mother’s Day and Father’s Day Sales

These sales show up in May and June respectively. Retailers offer deals on gifts like jewelry, gadgets, clothes, and experience packages. The promotions usually kick off a few weeks before each holiday.

Mother’s Day in May and Father’s Day in June
Focus on gift-oriented products
Special promotions and bundles

If you’re the type who waits until the last minute to grab a gift for Mom or Dad (again, no judgment), these sales can bail you out. Both online and in-store deals are easy to come by.

Valentine’s Day Sales

Valentine’s Day Sales focus on all the romantic stuff — chocolates, flowers, jewelry, and experience gifts. These promotions start showing up in late January and run through early February.

Observed on February 14
Gift-focused promotions
Both small businesses and major retailers participate

Whether you’re going all out or keeping it simple, the sales make it easier to find something special without totally emptying your bank account. Restaurants and experience companies often run deals during this window too.

Easter Sales

Easter Sales coincide with the holiday, usually showing up in March or April. Retailers offer deals on holiday merchandise, spring clothing, and candy. Sales typically start a few weeks before Easter weekend.

Observed during the Easter holiday
Includes seasonal and holiday items
Widespread participation by retailers

Families stock up on decorations, candy, and Easter outfits. It’s also when retailers start pushing spring inventory, so you can find deals on lighter clothing and outdoor items alongside the seasonal stuff.

Memorial Day Sales

Memorial Day Sales kick off summer in a big way. You’ll find discounts on outdoor gear, home improvement supplies, summer clothes, and even cars and travel packages. It’s one of the bigger shopping weekends of the year.

Observed on Memorial Day weekend in May
Focus on summer products and outdoor items
Participation by diverse retailers

This is when a lot of people make their big summer purchases. New patio furniture, a fresh wardrobe for the warm months, maybe some tools for summer projects. Retailers go big with both in-store and online promotions to get the season rolling.

4th of July Sales

4th of July Sales celebrate Independence Day with deals on patriotic gear, outdoor equipment, summer essentials, and more. These sales usually start in late June and carry right through the holiday weekend.

Observed around July 4
Focus on festive and summer items
Retailers from various sectors participate

It’s a fun shopping weekend because it lines up with cookouts, fireworks, and summer gatherings. Retailers ride the festive mood with solid discounts across the board, so it’s worth browsing even if you’re not specifically looking for something.