8 Cheap and Cozy Winter Dates To Go On In Toronto

8 Cheap and Cozy Winter Dates To Go On In Toronto

When the cold weather hits, it can be tempting to stay bundled up inside hibernating for the next four to six months (or however long it takes until we see the sun again). With snow on the ground and temperatures in the double negatives, the last thing on anyones mind is going on a date. But this year don’t let your love life catch the winter blues. These cheap and cozy winter dates will make you fall in love with the city you live in – and maybe even with that special someone you bring along with you. 

Here are 8 fun and cheap winter dates to go on in Toronto!

Spend a Friday Night Live at the ROM 

cheap winter dates

Until the end of November, the Royal Ontario Museum is hosting an art-filled Friday night bash. Discover the ROM like never before with food, drinks, and musical performances. Want to impress your date with your stunning art and history knowledge but can’t make it to the party? Not to worry, on the third Tuesday of every month admission to the museum is totally free!

Explore the Toronto Christmas Market 


The annual Toronto Christmas Market is a must-see attraction in the months leading up to the holidays. If you haven’t been, then you definitely need to check it out and if you have then you know how magical it is. Stroll hand in hand with your date as you browse the vendors for unique gifts and tasty winter treats. With Christmas carollers singing in the background and Christmas lights giving off a romantic glow, it will feel like a scene from a Christmas movie. All the holiday fun starts on November 14 and admission is free Monday to Thursday, but will only cost you $8 on the weekend.

Go For A Skate at The Bentway 

Skating is such a classic and fun winter activity – making it an obvious idea for a cute and casual date. For an under-the-radar spot, you and your date can avoid the crowds of tourists at Nathan Phillips Square and head to The Bentway to slip on your skates instead. This outdoor event space under the Gardiner Expressway opened last year and transforms in the winter into a winding skating trail. 

Catch a Concert at the Danforth Music Hall 

cheap winter dates

If you and your significant other are live music fans, then a concert might just be the perfect date for you guys. A show at iconic Toronto music venue, Danforth Music Hall is your chance to see an up-and-coming artist in a more intimate setting. Who knows, you might even get to see the next Drake or Shawn Mendes. For some pre-concert fuel, the venue just opened its own restaurant, the Danforth Sidebar.

Go for A Drink

cheap winter dates

Going for drinks is, understandably, the most common first date idea. It’s a low-pressure way to get to know someone in a casual environment, and the drinks help chase away any first date nerves. If you’re looking to switch it up a bit, we recommend going to a speciality bar this winter. After all, the best thing about winter is the excuse to drink all the warm drinks we were too sweaty to have in the summer. Her Father’s Cider Bar + Kitchen on Harbord has a selection of over 100 ciders to choose from, so you and your date can compete to find the best tasting one. 

Watch a Movie at the Paradise Theatre

cheap winter dates

This historic Toronto theatre is reopening on December 6 after a major renovation just in time to host your winter movie dates. The theatre will show a mix of new films and older classics as well as a variety of live shows. The art deco building will add a vintage feel to your date, giving it much more character than just seeing the newest blockbuster at the movie theatre at your local mall.

Experience the Toronto Light Festival

From January to March, The Distillery District is being transformed into a visual experience put on by the Toronto Light Festival. This is the third year for the festival, so you know it’s going to be better than ever before. You and your date can check out all the colourful exhibits and admire the incredible light instillations. 

Try Toronto’s Best Restaurants with Winterlicious 

cheap winter dates

This yearly event is a food lover’s dream. Nearly 200 of Toronto’s best restaurants participated last year, offering three course, prix fixe menus at special prices. This is the perfect opportunity for you and your date to try out some of the best flavours our city has to offer. Winterlicious is back from January 31 until February 13 so mark your calendars!

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