Date Guides Date Ideas


Guide to the 25 Best Winter Date Ideas

Winter blues got you down? Tired of doing the same things over and over again? We’ve got you covered! Here is our list of the 25 Best Winter Date Ideas to help you create new experiences with the people you love! Take you love, parents, gals, guys, grandparents, anyone! Life is about making the most of the time we have together, so why not try something new, or enjoy an old classic, as you make a memory!

1. Skate on an Outdoor Trail

This is SO fun and is definitely different than skating in an indoor rink! Some trails even light up at night! Look up the one closest to where you live! Some examples are Arrowhead Provincial Park or Blue Mountain in Ontario!

2. Go to a Tree Farm

*Cue Taylor Swifts new song* Even if you’re not getting a tree, this is still cute! If it’s past the Christmas season, farms usually still open and have to cutest bakeries inside! Grab a hot chocolate and walk around the tree farm enjoying the snow (if you have any where you live)!

3. Host a Cocktail Exchange Party!

Who doesn’t love trying new drinks over the winter?! Basically: have a party (be sure to know how many people there will be), tell everyone to come ready to make a cocktail for the group! You can even use a signup sheet so people don’t make the same ones! We had SO much fun with this and got to try so many new wild drinks we’d never heard of before! Caution* Be prepared for a headache the next morning from all the sugar…and alcohol haha!

4. Go Indoor Rock Climbing or Go-Karting

Get your exercise on! (We know it’s bulking szn, and you’d rather hibernate, but get out there). Have you actually done indoor rock climbing before? It is SUCH a good workout, and is honestly such a fun time with a group of friends or even solo! Indoor go-karting is also a blast!

5. Walk through a Botanical Gardens!

It will be a winter wonderland! Most Botanical Gardens usually have an indoor and outdoor setup so you can check out the greenery in either spot!

6. Have a Staycation

A.K.A. Book a night at a local hotel! A change of scenery is good for the soul! Who actually gets to enjoy the amenities of a hotel when you’re on the go and traveling? Not many! Enjoy the spa, restaurants, pool, and anything your hotel has to offer and RELAX!

7. Check out your Local Art Gallery

Art Galleries usually have new exhibits over the holidays and winter season! Grab a drink and walk around admiring all of the talent in our world! Try to guess what each piece of art is trying to portray, always a fun time!

8. Go to an Escape Room

This is great for double/triple dates, or groups of friends! Watch the competitive side come out as everyone has an hour to escape a room with different puzzles to solve! These have gotten increasingly popular over the last few years, and well, it’s because they’re a great time!! You definitely have one near you, they’re popping up in almost every city!

9. Try ice wines in the Winter!

Some of my friends in other countries had never heard of ice wine before, so I’m not sure if you know about it or not, or if it’s only a Canadian thing! Ice wine is made from grapes that are harvested just as they start to freeze over in the colder temperatures. It is a pricier, more luxurious wine as it takes a larger number of grapes to make a small amount of wine. This is usually known as a “dessert wine.” Niagara Falls has an IceWine Festival every January and is delicious!

10. Rent a private room in a Karaoke Bar!

Belt your heart out! If you dislike the cold like us, finding fun activities indoors is a must! Most larger cities have rentable Karaoke rooms. Bring your friends, the whole family, anyone would enjoy a singing to your favourite songs!

11. Go Snow Tubing

Sure, you can go skiing or snowboarding, but have you been snow tubing? Release your inner child in this adult toboggan adventure! Most ski resorts have snow tubing options and are open for the winter season!

12. Take a Cooking Class

Spice things up in the kitchen! Learning and TASTING new recipes is always a good thing! Let your tastebuds try something new! In Canada, try looking up “PC Cooking School” The grocery stores near you offer classes, and you get to choose your menu!

13. Take a Pottery Class

Don’t be afraid to get messy- you will! We did this a few years back! I remember wanting to try this for so long, and wow, was it a challenge lol! Much more difficult than it looks, but you can have so much fun with the process as you mold, shape, and paint your pottery! Let your creative side shine!

14. Try a Food Box Delivery Service!

We are pretty addicted to these. We’ve now order them once a month so we can try new recipes! We order 3 meals for 2 people and always end up with leftovers! Our favourite company to order with is Goodfood! They seriously have such a great variety of choices, and the meals are to die for! We’ve been getting their food for almost a year now! Click here if you want $40 off your first box!

15. Go to an Arcade

Let your inner child out and play some old school video games or arcade games! Every city has an arcade bar somewhere! Most bowling alleys also have an arcade attached to them! Have fun with Pac-Man or Donkey Kong, and have a few drinks while you play!

16. Visit the Zoo

Since it’s winter, many animals are placed in enclosed shelters, so you can get SO much closer to them! We experienced this at the Toronto Zoo when we went during the colder months! Obviously make sure the zoo is humane, and doing the right thing!

17. Go to a Spontaneous Concert

Look up a smaller venue near you. Buy tickets for the next thing that pops up! Or for a genre you enjoy! We’ve never had a bad time at a concert. Rocking out to music in a room full of people that belt out the songs is always a great atmosphere to surround yourself in!

18. Go on a Local Winery or Brewery Tour

If you’re like us we LOVE wine and beer! Supporting local is always a good thing, on top of trying new flavours of beer or wine! We always have a blast going for a tour or tasting! We’re lucky enough to live near Niagara–on-the-Lake that has SO many amazing wineries! We wrote a blog post on the perfect day in Niagara! Click here to check it out!

19. Go Snowshoeing or Cross-Country Skiing

Has anyone actually done this before? WOW is it a workout, but such a blast! Definitely a new experience

20. Spa Day!

Enjoy a day at the spa! Go for a couples massage, relax in the sauna or by the pool, and spend time RELAXING! Taking time for yourselves is rare in our world today, everyone needs a little physical and mental break from time to time!

21. Visit a Cat Cafe or Volunteer at an Animal Shelter

Even though we are #catobsessed they honestly are the cutest things! Most have a small entry fee that goes toward taking care of the cats until they get adopted. We love visiting the one in Toronto! Or, if you can volunteer your time at a local animal shelter, we promise your heart will feel SO full!

22. See a Play or go to a Comedy Show!

The Nutcracker is always a good choice this time of year (if it’s around Christmas), or else we LOVE comedy shows. They say laughter is the best medicine and boy is that true! Everyone needs a good laugh every once in a while, and supporting local talent is the best!

23. Play a new Board Game or go to a Board Game Cafe

Honestly we love a good board game night every once in a while. Sometimes you’re limited if there are only 2 of you! One of our favourites when there are few people is this serious, yet hilarious question game. Get the conversations rolling with “Table Topics” Trust us, you’ll love it! Or, see if there are any board game cafes near you. Order some drinks and play from their endless selection of games!

24. Try a new Coffee Shop

I swear the aesthetic of all the new coffee shops popping up everywhere is a designers dream! Visit a new coffee shop in your hometown. Cozy up with your phones away and chat for hours like it’s your first date!

25. Play “Groupon Roulette”

Don’t knock it ’til you try it! Basically, set your location, set a max price, choose the “Things To Do” category on the Groupon App, close your eyes, scroll for as long as you want with your eyes closed, andddd STOP! Buy what you landed on! We’ve done this before and it is always something hilarious and random! Enjoy!!

Well there you have it! 25 of our favourite winter date ideas! Make sure you get a date night in at least once a month! You deserve that time! If you do any of the ideas above be sure to tag us in it, @thethompsontrotters. We love seeing people use our suggestions!

S & S

Live in the Toronto area? You can also check out our post on
The Top Things to do in Toronto this Winter!

25 Best Winter Date Ideas
25 Best Winter Date Ideas

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  • Reply
    Nicole Claesen
    February 8, 2020 at 8:31 pm

    Great date ideas!! Love the cooking class idea. I also really like visiting a cat cafe or volunteering at an animal shelter. Going to a botanical garden is another great one too. Now I need to plan a date with my Hubby 🙂

    • Reply
      February 10, 2020 at 3:37 am

      Yes get out there haha! Hope it gave you some inspo!

  • Reply
    Tiana Bantis
    February 9, 2020 at 2:24 am

    These are such cute winter ideas! I love the idea of groupon roulette and a cooking class!

    • Reply
      February 10, 2020 at 3:36 am

      We loved the cooking class with PC so much!!

  • Reply
    February 10, 2020 at 1:49 am

    These are so great! I really would love to go on more local brewery tours if I can. 🙂

    • Reply
      February 10, 2020 at 3:36 am

      That’s our favourite thing!!

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