Winter Is Coming, Canada: The Best Winter Gear & Cold-Weather Deals for 2026
The best winter deals on WagJag right now are the Unisex Heated Winter Jacket for $71.95 (69% off), Heated Touchscreen Gloves for $37.95, Rechargeable Heated Insoles for $19.95, and women's waterproof winter boots from $29.95. For cold-weather plans, top picks include the drive-through holiday light show A Journey Into Enchantment in Ajax, 25% off Cinderella at Canadian Stage (December 5 to 18, 2026), and 2-night waterfront cottage stays in Ontario for $375.
Canadian winter deals at a glance
| Deal | WagJag price | Regular value | Savings |
|---|---|---|---|
| Unisex Heated Winter Jacket | $71.95 | 69% | |
| Women's High Cut Winter Boots | $39.95 | 69% | |
| Women's Waterproof Snow Boots | $43.95 | 67% | |
| Women's Waterproof Winter Shoes | $29.95 | 62% | |
| Winter Windproof Ski Hat | $21.95 | 60% | |
| Heated Touchscreen Gloves | $37.95 | 52% | |
| Rechargeable Heated Insoles | $19.95 | 49% | |
| Hibachi Teppanyaki Dinner | $79 & up | 50% | |
| Ontario Waterfront Cottage, 2 nights | $375 | 42% |
Winter is coming to Canada
The first real cold snap always seems to catch us off guard. One morning a light fall jacket is fine. The next, the wind cuts right through it and you're searching for gloves before you've reached the car.
Most Canadian families know the routine. The front hall closet turns up one mitten, a toque that's seen better days, and boots stained white from last year's road salt. Then the first big storm arrives, and the store shelves are picked over and back to full price.
This year, there's still time to get ahead of it. As of October 20, WagJag has dozens of winter gear and cold-weather deals live, with savings of up to 69%. True north, strong and freezing—and this time, prepared.
Below are our top picks, grouped by what matters most: warm hands and feet, dry boots, the right outer layers, and indoor outings and holiday events the whole family can enjoy when it's -20 with the windchill and dark by 5 p.m.
What's the best heated winter gear for Canadian winters?
Cold hands and feet are usually what cut a winter outing short, so they're the best place to start. Even the warmest coat can't help much if your toes are numb at the bus stop.
Heated gear has become much more affordable, and these deals bring it well below retail:
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Heated Touchscreen Gloves
$37.95$79More than 270 sold. Touchscreen fingertips let you use your phone without taking them off.
View Deal -
Rechargeable Heated Insoles
$19.95$39Fit into the boots you already own and recharge between uses. Ideal for long walks and outdoor sports.
View Deal -
5 Pairs of Women's Winter Warm Socks
$22$50An easy way to restock the sock drawer before the season starts.
View Deal
Best waterproof winter boots on sale in Canada
Wet feet get cold fast. Once sidewalks fill with slush and road salt, a waterproof boot with good grip makes every walk safer and more comfortable.
Many of the styles below pair waterproofing with warm linings, and several are among WagJag's top sellers this season.
For her
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Women's Waterproof Winter Shoes
$29.95$79The top seller in the category, with more than 700 sold.
View Deal -
Women's Waterproof Snow Boots
$43.95$134.99One of the deepest discounts on full snow boots.
View Deal
For him
Tip: order boots now rather than the week of the first storm. That leaves time to check the fit and break them in before you need them.
Winter coats, toques and accessories deals
If you're upgrading just one item this year, the heated jacket offers the most value:
Unisex Heated Winter Jacket
A jacket with built-in heating, useful for long commutes, outdoor rinks and clearing the driveway.
View DealFor more traditional options:
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Women's Long Winter Jacket
$55.95$110A longer cut for extra coverage on cold, windy days.
View Deal -
Women's Mid Length Winter Coat
$60.95$120Velvet lining, hood and an adjustable drawstring waist.
View Deal
Hats and face coverings are easy to overlook, but they make a big difference on windy days. Matching sets cover hat, scarf and gloves in one order, which makes outfitting the kids simple:
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Thermal Winter Face & Head Cover
$19$41.50Worth having on hand for days when Environment Canada issues an extreme cold warning.
View Deal -
3-Piece Kids Winter Hat, Scarf & Gloves Set
$26$39.99Sized for ages 4 to 10, in seven colours.
View Deal -
3-Piece Men's Wool Hat, Scarf & Touchscreen Gloves Set
$26$34.99A complete cold-weather set in four colours.
View Deal
There are 71 winter gear deals in total, so if you don't see your size or style here, browse the full collection.
Indoor things to do in Ontario this winter
Cold weather doesn't have to mean a season spent indoors on the couch. A few planned outings give kids somewhere to burn off energy and give the whole family a break from screens, whether it's between hockey practices or over the holiday break.
Booking now, while prices are low, means you'll have plans ready when the weather turns.
Active fun for the whole family
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Aerosports Trampoline Park$19.99 & up
A 120-minute jump pass at 5 locations.
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Steel Peak Climbing$19 & up
Day passes for 1, 2 or 4 people.
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Bingemans Bowling$39.95(an $82.95 value)
A 1-hour lane with shoes for up to 6 people.
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ReptiliaOver 30% off
General admission at 3 locations. A warm, hands-on learning outing for curious kids.
Unique experiences
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uFly Simulator$99(a $289.90 value)
A 1-hour flight in a replica 777 cockpit for up to 2 people. A memorable gift for aviation fans of any age.
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Escape The House$39.99 & up
An escape room for 2, 4 or 6 people.
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2 tickets and a bucket of popcorn, a good pick for an adults' night out.
Upcoming events
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Ottawa Pet Expo$20 & up
October 24 & 25. Tickets for 2 or a family pass. Note that it takes place this weekend.
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National Women's ShowUp to 30% off
November 6 to 8.
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Salon du Chocolat Toronto$12.50 & up
1-day and family passes to this November chocolate festival.
Halloween fans can still find deals on SCREEMERS and Pumpkins After Dark through the end of October.
Holiday events and winter getaways in Ontario
December fills up quickly. Planning a few outings and meals in advance keeps the season focused on time together rather than last-minute scrambling.
Holiday outings
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A Journey Into Enchantment, Ajax$24.80 & upper vehicle
Because it's a drive-through light show, the whole family can enjoy it from a warm car.
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Cinderella at Canadian Stage25% off
December 5 to 18, 2026. Use promo code wagjag. A classic holiday outing to share with the kids.
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Evil Dead The Musical20% off
Use code WAGJAGEVIL26. A horror-comedy musical for adults and older teens looking for something different this season.
Warm up at the table
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Hibachi Teppanyaki & Bar$79 & up
A seven-course teppanyaki dinner for 2 or 4 at 9 locations. With nearly 24,000 sold, it's one of WagJag's most popular deals.
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Oggi Bistro$79.20 & up
A 3-course dinner with wine, plus a $25 gift card.
Get away for a weekend
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A 2-night waterfront cottage stay in Ontario's Kawartha Lakes region. A quiet winter break by the water.
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Wyndham Grand Fallsview Hotel$149 & up
A 1-night stay with views of Niagara Falls. Ice forming along the gorge makes winter one of the most striking times to visit.
Canadian winter FAQ
When is the best time to buy winter gear in Canada?
Late October and early November. Stock is still full, sizes haven't sold out, and deals are already live—WagJag's winter boots and coats are up to 69% off right now. Waiting until the first big snowfall usually means fewer sizes and higher prices.
How do I keep my hands and feet warm in a Canadian winter?
Layer up and add heat. Wool-blend socks plus rechargeable heated insoles ($19.95) handle your feet, and heated touchscreen gloves ($37.95) keep your fingers working. Waterproof boots matter just as much, because wet feet get cold fast.
Are heated jackets worth it?
For long outdoor stretches like commuting, shovelling, or watching an outdoor rink game, yes. They add warmth without bulk. WagJag's Unisex Heated Winter Jacket is $71.95, down from $229.
What are fun indoor things to do in Ontario in winter?
Trampoline parks, rock climbing, bowling, escape rooms, comedy clubs, and flight simulators are all on sale on WagJag. Popular picks include Aerosports Trampoline Park from $19.99 and Steel Peak Climbing from $19.
Is there a drive-through holiday light show near Toronto?
Yes. A Journey Into Enchantment in Ajax is a drive-through light show, and WagJag has vehicle admission from $24.80.
How do I use a WagJag promo code for holiday shows?
Some event deals come as a promo code instead of a voucher. For example, use wagjag for 25% off Cinderella at Canadian Stage (December 5 to 18, 2026), or WAGJAGEVIL26 for 20% off Evil Dead The Musical. Each deal page has the full instructions.
How to get ready for a Canadian winter: your 10-minute plan
You can cover the essentials in a few minutes:
- Do the closet check tonight. Pull out every glove, hat and boot. Set aside anything with holes, worn linings or cracked soles.
- Fill the gaps, warmest first. Hands and feet, then boots, then the coat. That order gives you the most comfort for your money.
- Book one indoor plan for November and one for December. Put them on the fridge. Having something on the calendar makes the shorter days easier.
- Plan one cozy splurge. A cottage weekend, a teppanyaki night, a show. It gives everyone something to look forward to in the middle of the season.
Ready for winter?
Winter will arrive right on schedule, as it always does. With the right gear and a few plans in place, your family can enjoy it instead of just getting through it.
Prices and availability as of October 20, 2026. Deals can sell out or change, so check the deal page for the latest details.