If you haven't hopped on the cuffing season bandwagon yet, you'd better get moving. You may say that you enjoy being single now, but come mid-December, when all your friends are posting cute snaps of their dates with their boo, you're gonna wish you weren't at home in your PJ's alone, watching Elf for the 20th time this month.
I'll be the first to say it; there's nothing better than love, especially during the holiday season. Visiting all the beautiful Christmas light displays, sipping on hot chocolate after a skate date, and attending fun, unique winter festivals are so much better with the person you love by your side. If love isn't really your thing, though, you can totally do all these things with your best friend too 😉.
Winter in Calgary is something every Albertan should experience at least once. Sure, it's been known to get pretty cold and snowy, but if you can look past that and throw on your jacket and some boots, you'll have the time of your life. From Zoolights to skating at Olympic Plaza, and The Nutcracker Ballet to the CP Holiday Train, there's plenty to do and see this holiday season. You and your boo will never run out of things to do, thanks to this awesome list we've compiled for you:
What are you looking for?
Super Fun Romantic Dates
Super Fun Classy Things
Super Fun Free Things
Super Fun Places to Eat and Drink
Super Fun Cheap Things
For Super Fun Romantic Dates, click "Next".
Lloyd's Roller Rink
Where: 7520 Macleod Trail SE // Kingsland
With the recent news of the upcoming closure, you'll definitely want to check out Lloyd's Roller Rink while you still can. Grab a bite to eat and skate around this super cute and retro spot.
Inner Balance Spa
Where: 424 10 Street NW // Hillhurst
Treat yourself to a couples day at the spa. With it's aesthetically pleasing decor, natural and organic ingredients, and alternative therapies, you'll definitely find a service to enjoy here, such as acupuncture, or their Infrared Sauna.
Zoolights
Where: Calgary Zoo // Bridgeland
No one loves Zoolights more than couples; it's not only super fun, but also super romantic. This year's 20th anniversary is sure to be bigger and brighter than ever, with over a million lights to see and admire.
Banff Upper Hot Springs
Where: 1 Mountain Ave // Banff
If you happen to be heading to the mountains at all, you'll want to stop at the Banff Upper Hot Springs and take a dip so you and your loved one can get some of the relaxation you deserve.
Calgary Flames Game
Where: Scotiabank Saddledome // Stampede Grounds
Maybe not everyone considers this romantic, but any hockey fanatic will jump at the chance to head over to the Saddledome and watch a Flames game.
Ski Day
Where: Sunshine Village // Banff
Something about ski lodges is super romantic; maybe it's because they always give me throwback High School Musical vibes. Take your boo to the mountains for a day they'll never forget.
Dinner with a view at Sky 360
Where: Calgary Tower // Downtown
The Tower is always a local YYC favourite because the view is incredible, but in the winter, it gets even better. Enjoy a romantic dinner as you overlook the city, and all the pretty lights and sights to be seen.
A Christmas Carol
Where: 240 9 Ave SE // Downtown
Theatre patrons will love this one. A Christmas Carol is a holiday classic, that's even better enjoyed in the company of your s/o.
For Classy Things, click "Next".
The Nutcracker
Where: Southern Alberta Jubilee Auditorium // Hillhurst
What's classier than a date to the ballet? The Nutcracker is running from December 15 - 24th, so you have plenty of opportunities to check out the show.
Bottle Service at Bespoke
Where: 736 10 Ave SW // Downtown
Bespoke is one of YYC's best nightlife spots, playing great music and providing awesome bottle service options for you and yours to have a crazy night out.
Brunch in Heritage Park
Where: 1900 Heritage Drive SW // Eagle Ridge
Heritage Park currently has their Once Upon A Christmas festival, which is perfect for getting you into the holiday spirit. They also offer Sunday brunch, but tickets sell out quickly, so you'll want to purchase quickly.
Rent a cabin for a weekend getaway
Where: Any of these cozy cabins near Calgary
Most people save getaways for the summer, but something about a winter getaway screams romance. Cozy up in a cute little cabin and stay warm by the fire this holiday season.
Go Stargazing
Where: Rothney Astrophysical Observatory // 40 mins outside Calgary
It may be too cold to lay out a blanket, but that doesn't mean you can't stargaze. Drive a bit outside the city and admire the gorgeous winter night sky.
Plan a roadtrip from Calgary to Seattle
Wanna be Sleepless in Seattle? We've got your roadtrip itinerary covered, all you need to do is pack your bags, hop in the car and drive.
Grab drinks at Proof Cocktails
Where: 1302 1 Street SW // Downtown
Proof is one of the classiest places to grab a drink in Calgary. Their menu is super unique, and is formatted like a storybook for your enjoyment.
Grab some drinks at National on 10th
Where: 341 10 Ave SW // Downtown
Super cozy, and super classy, National is the perfect spot to spend a Saturday night with your s/o. They've got a great drinking menu, and an even better selection of food.
For Free Things, click "Next".
Enjoy the view at Scotsman's Hill
Where: Scotsman's Hill // Downtown
When: Anytime!
Every Calgarian knows that if you want a view of the city, this is the place to be. Grab some hot chocolate and enjoy the gorgeous cityscape with your s/o.
Lions Festival of Lights
Where: Confederation Park // Queens Park Village
When: Open every night until January 8th from 6 p.m. to midnight
One of the best things about this season is the many opportunities for cute couple pics for your IG. Christmas lights always make for super great photos.
Skate Nights with DJ CLAUZ
Where: Olympic Plaza // Downtown
When: Every Saturday night in December from 5:30 to 9:30 p.m.
Make your skate date even more fun. On Saturday nights, you can find a live DJ at Olympic Plaza, playing all your favourite Christmas music while you, hopefully, try not to fall.
Visit Contemporary Gallery
Where: 117 8 Ave SW // Downtown
When: Wednesday - Sunday from 12 p.m. to 6 p.m.
We've had a pretty tame winter so far, but when the weather starts to get nasty, keep warm with your boo and head over to the Contemporary Gallery to explore and admire some art.
Canadian Pacific Holiday Train
Where: Anderson C-Train Station // Southwood
When: December 9th from 6:45 - 7:45 p.m.
The Holiday Train comes once a year, and is sure to brightly light up your holiday season. The cost is free, but you can bring a donation for the local food bank in the spirit of giving.
Marshmallow Roast in Bowness
Where: 8900 48 Ave NW // Bowness
When: Anytime!
S'mores don't need to be limited to the summer. Take a walk in Bowness this winter, and pack a picnic of hot dogs and marshmallows that you can roast over an open fire.
Christmas in Kensington
Where: Kensington
When: Every Saturday from 12 - 4 p.m.
Snap a picture with santa, take a sleigh ride, or catch a free movie. There's plenty to do in one of Calgary's trendiest neighbourhoods.
Hike through Nose Hill Park
Where: 1320 5th Ave NW // Sunnyside
When: Anytime!
Nose Hill is another Calgary hot spot, and is great if you're looking to get outside and enjoy some fresh air. If you have a dog, this is a great spot to go for a stroll, or if you just happen to like dogs, you'll see some here for sure.
For Places to Eat and Drink, click "Next".
Native Tongues Taqueria
Where: 235 12 Ave SW // Downtown
Calgary probably isn't the first place that comes to mind when you think tacos, but you don't want to miss out on Native Tongues. The restaurant is beautifully decorated, and the menu is phenomenal.
Ship & Anchor Pub
Where: 534 17 Ave SW // Downtown
The Ship is a super cool, hipster hangout on 17th. Everyone there is super welcoming, and you'll be able to get drunk without breaking the bank.
Anju
Where: 344 17 Ave SW // Downtown
Korean food is becoming super popular in Calgary, and if you're part of the movement, you'll want to add Anju to your bucket list. The KFC Sliders are a fan favourite, but in all honesty, the entire menu is worth trying.
Run Pig Run
Where: 529 17 Ave SW // Downtown
This Urban Eatery & Bar has become a YYC hot spot, with live music on weekends, and a great food and drink menu. You'll want to keep coming back for more.
The Coup
Where: 924 17 Ave SW // Downtown
If your s/o is a vegetarian, they'll beg you to take them here. Delicious, affordable vegetarian food can be hard to come by. The Coup offers all of that, on top of great service, and a beautifully decorated interior.
Cafe 100%
Where: 30 Country Hills Landing NW // Country Hills
Cafe 100% is known to be quick, delicious, and reasonably priced. The interior is tasteful and well decorated, and the menu has something everyone will love.
Pizza Brew - Minha's Micro Brewery
Where: 1314 44 Ave NE // McCall Lake Area
If you've ever wanted to watch the beer making process before enjoying a cold one, look no further. Minha's also makes all kinds of tasty wines and hard sodas.
Pacini
Where: 123 Freeport Blvd NE // Near Airport
Winter is here, and you need to bulk up so you can stay warm. The perfect way to do that? Ingest a ridiculous amount of carbs.
For Cheap Things, click "Next".
Market Collective Cheer
Where: 1390 17th Ave SE // Inglewood
Why you should go: In terms of Calgary markets, the Market Collective is always a favourite. Hosted in one of the cities most quaint and artsy neighbourhoods, this market features food trucks, live music, and an abundance of incredible vendors. Head on over on December 1st - 3rd, 4 p.m to 9 p.m on Friday, 10 a.m to 6 p.m on Saturday and Sunday.
Ugly Sweater Decorating
Where: At home!
Chances are good that you'll be invited to at least one ugly sweater function this holiday season. Get ahead of the game and decorate matching ones with your s/o.
Grab Shisha and relax
Where: Any of Calgary's great shisha bars
Shisha is always fun, no matter who you're smoking it with. Calgary has lots of great places, but RIOT, Arabesque, and Fire & Ice are our favourites.
Escape Hour
Where: 3016 19 Street NE // Vista Heights
Escape rooms have become a popular date spot. Calgary does have quite a few, but Escape Hour is one of the best. They've got a total of four escape rooms, all of varying difficulties. Which can you solve fastest?
Karaoke at Ducky's Pub
Where: 2100 4 Street SW // Mission
What better way to get to know your s/o than to watch them attempt to sing their favourite song while drunk? Karaoke is always a great date idea, and Ducky's is one of the best spots in Calgary to try it.
Monster Mini Golf
Where: 2020 32 Ave NE // Vista Heights
First of all, how cute would this place look on your Insta feed? Glow in the dark mini golf is something everyone needs in their lives. For just $13, you can play a round.
Flying Squirrel
Where: 572 Aero Drive NE // Near the airport
You're never too old for some classic trampoline fun. Flying Squirrel Calgary has 13 attractions, including dunk hoops, a dodgeball court, and a foam pit.
TELUS Spark
Where: 220 St Georges Drive NE // Bridgeland
TELUS Spark is always one of the coolest places to visit in Calgary. With new exhibits popping up on the regular, you're always bound to learn something new.
B.C. Green Leader Emily Lowan following a media availability in Victoria, B.C., on Wednesday, Sept. 23, 2026.
THE CANADIAN PRESS/Kevin Light