5 New Toronto Date Ideas For Your September


Is it seriously September already? Date nights are changing from picnics and patio dinners to cozy and cool evenings (and the resurgence of all things pumpkin).

Whether you thrive in the cooler weather, or hate the fact that you’ll have to throw on a jacket over your outfit, there’s tons of unique date ideas coming to Toronto this month!

Check out these five new events coming to Toronto and the GTA this September:

Night Market TO

Head to Mississauga at the Square One Shopping Centre parking lot to find a collection of delicious local food trucks at this night market! They’ve been operating every few weeks throughout the summer with themes like Taste of the Caribbean, All You Can Eid, and now Hot Grill Summer for the long weekend!

Enjoy eats from Buster’s Sea Cove, Heirloom Toronto, The Smoke Stop BBQ, Meltdown Cheesery, the iconic Holy Grill TO and more. Open Friday September 3rd through Sunday September 5th 3pm till midnight and Monday September 6th they’re open from 2pm till 11pm. Admission is free!

Miss it? Stay updated for more markets coming on their Instagram!

Toronto International Film Festival (T.I.F.F)

If Toronto’s famous for one thing (other than Drake), it’s for TIFF taking place downtown every September. The 46th edition of the Toronto International Film Festival is back this year from September 9th-18th. The festival features close to 200 international and Canadian films in its Official Selection.

Enjoy in-cinema, drive-in, and open-air cinema screenings at locations all around the city including: TIFF Bell Lightbox, Roy Thomson Hall, Princess of Wales Theatre, Scotiabank Theatre, and Ontario Place. There’s also options to watch from home with tickets for TIFF’s digital film screenings.

Festival Village will be in Ontario Place this year featuring the Cinesphere IMAX Theatre, the Visa Skyline Drive-in, the RBC Lakeside Drive-In, and the West Island Open Air Cinema.

Find tickets here.

Niagara Grape and Wine Festival

For wine lovers, the Niagara Grape and Wine Fest is a staple in wine country since 1951! The 70th Grape & Wine season will look a little different this year, but there’s plenty of fun to be had and wine-loving dates to explore.

There’s two fun options this year: Purchase a Grape & Wine Discovery Pass to tour and taste at your choice of six out of 20 Niagara wineries. You can also attend the Best of Montebello Park Outdoor Concert Series at the St. Catharines‘ First Ontario Performing Arts Centre.

This is all happening during the September 18-19 and 25-26 weekends.

Fall BeerFest TO

If wine isn’t your thing and you and your beer-loving date are missing festivals, FallBeerFestTO is here for you!

Head to the Bandshell Park at Exhibition Place on September 24th-25th for this outdoor celebration of beer. Sip on local and international beer paired with food curated by Toronto’s most beloved restaurants while live music plays around you.

Shaggy will be performing on Friday the 24th and Toronto’s favourite cover band, Dwayne Gretzky, will be playing on Saturday the 25th.

Tickets are on sale now and include 5 tasting tokens and admission. Or, upgrade your ticket to a VIP for ultimate access.

The Road Trip by Toronto Cider Fest

Toronto Cider Fest is back, with an event on the road. This September event used to operate on the ground of Sherbourne Commons for days of cider, food, and music-filled fun and have now announced their Road Trip experience, on until October 11 (while tickets last).

For this road trip, you have the option of two adventures for you and your date to embark on:

This experience is designed for two people, perfect for an end-of-summer date and whichever route you pick, the package include:

  • An exclusive cider-and-dine experience at the location with cider tastings plus two premium ciders of choice
  • A mouthwatering charcuterie board to compliment the cider experience
  • A curated road trip itinerary with spot to check out on the way and around the area
  • Access to an exclusive Cider Dest playlist by DJ D Smooth
  • A surprise gift bag to take home

Get your tickets and find out more at their FAQ!

Yorkville Murals

Toronto’s Yorkville Murals is back! This annual three-day event brings public art to the walls of Yorkville. Grab an ice cream, coffee, or go out shopping in the village and browse the gorgeous murals from September 24-26th!

Find all the art, and read more about the initiative here.

You can also check out other great ideas for date night in Toronto right here! Let us know what else you would like to see for date night so we can check it out. 

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