It's finally the best time of the year! The season for Pumpkin Spice Lattes, oversized sweaters and pumpkin picking- it's Fall! With the most romantic time of the year starting, you probably are thinking you've got to majorly step your date game up. 

Luckily for you, we've got 53 things that you and your bae can do during the cooler months in the city! From hiking and festivals to Stranger Things themed picnics in the park, we've got you covered all Fall long! 




For 'September,' click 'Next.'


via @allovsin

1. Make use of the last bit of warm weather by tackling this patio crawl. 

2. Going wine tasting at the Niagara Wine Festival (September 8th - 24th). 

via @mahddness

3.  Checking out a movie at the TIFF Cinesphere // 955 Lake Shore Blvd W (September 7-17).

via @nataliabedik

4. Getting cultural at the Toronto Ukranian Festival (September 15-17).

via @katie_hope8

5. Having a laugh at Just For Laughs 42 (September 21st-30th).

via @katbourolias

6. Going to the 5-Drive In for a unique spin on a movie date. 

via @that_glitter_chick_

7. Checking out Queen West Art Crawl at Trinity Bellwoods // 790 Queen St W (September 23-24).

via @rvsteiner

8. Attending the Invictus Games (September 23-30th). 

via @leftyscissors

9. Going café hopping during Pedestrian Sunday in Kensington (September 24th).

via @tooktoberfest

10. Celebrating your German heritage whether you are German or not at Oktoberfest (September 29th-30th). 

11. Checking out the immersive digital experience at EDIT (September 28th-October 8th).

via @nuitblancheto

12. Scoping out the art exhibits across the city at Nuit Blanche (September 30th). 

via @natty_dreds

13. Going strawberry picking at Whittamore’s Berry Farm // 8100 Steeles Ave E.

via @streetsoftoronto

14. Having a picnic at High Park.

via @uoftc4c

15. Roasting marshmallows over a bonfire @ Christie Pits Park // 750 Bloor St W. 

via @nicolexxx3

16. Going apple picking at Applewood Farm and Winery // 12416 Mccowan Rd Stouffville.  

via @mankinoh

17. Getting in the school spirit at a university homecoming! 

via @heymoniz

18. Checking out the Guillermo del Toro "At Home with Monsters" exhibit at the AGO (September 30th-January 7th). 

For 'October' click 'Next.'


via @alice_lo

19. Visiting Dundas Peak for a picture perfect hike. 

via @tw_fw

20. Channeling your inner Instagram influencer at Toronto Women's Fashion Week (October 2-7). 

via @living_europe

21. Spending your reading week abroad by booking one of these cheap vacas!

via @bluemountainvillage

22. Going to Fallacious at Blue Mountain (October 10th-November 30th).

via @alyssacabralxo

23. Setting up a picnic at Trinity Bellwoods and binge watching the new season of Riverdale (out October 11th). 

via @hurricaanne

24. Going to the Harry Potter Toronto Symphony Orchestra Show (October 12th-14th).

via @reinaiizuka

25. Going for a Fall trail ride on horse back at Claireville ranch. 

via @katrinacameron_

26. Visiting Muskoka for the Bala Cranberry Festival (October 14th-16th).

via @intheseats

27. Getting spooked at the Toronto After Dark film festival (October 12th-20th).

via @trevorodho

28. Channeling your inner beer snob at the Cask Days festival (October 20th-22nd). 

via @tedxtoronto

29. Going to a TEDx Talk at Evergreen Brickworks (October 27th). 

via @pizzalibretto

30. Grabbing some pizza from Pizzeria Libretto then going home to binge watch Stranger Things (out October 27th). 

via @savvy.stills

31. Trying to beat the corn maze at Whittamore’s Berry Farm // 8100 Steeles Ave E. 

via @sweetjesus

32. Getting Fall inspired lattes from Sweet Jesus. 

via @thushy_

33. Pumpkin picking at Downey's Farm Market // 13682 Heart Lake Rd.  

via @cee_walker

34. Going to a Leafs game. 

via @halloween.bests

35. Braving Halloween Haunt at Wonderland. 

via @belligerent.white.girl

36. Attempting to thrift a potential Halloween costume at Black Market.

via @mikeee67

37. Cheering on the Raptors at the ACC.

For 'November' click 'Next.'


38. Going on one of these road trips to see the Fall foliage. 

via @cadney

39. Satisfying your sweet tooth at the Toronto Chocolate Festival (November 1st-30th).

via @bacai.jpg

40. Warming up from the chilly weather by going to one of these pho spots for a lunch date! 

via @s_saamm

41. Being an Instagram foodie for a day and going to the coolest places for brunch, lunch and dinner! 

via @katyperry

42. Going to the Katy Perry Witness concert (November 1st).

buy tickets here.

via @tina_irwincanada

43. Watching horse jumping at the Royal Winter Fair (November 3rd-12th). 

via @lo.pitt

44. Checking out Toronto's first cider bar, Her Father's Cider. 

via @tentsile

45. Going on an adventure at the Dorset Fire Tower.

via @ericlapierre

46. Doing a spooky escape room at NOWAYOUT.

via @daisyenwrong

47. Going on the ultimate adventure at Scenic Caves Nature Adventures to get a last look at the autumn leaves.

via @nicola105

48. Biking through the Don Valley on the bike path.

via @angelalovessugar

49. Taking refuge from the chilly weather by playing some board games at Snakes and Lattes.

via @spinmaster

50. Swapping your PSL for a Santa hat at the Santa Claus Parade (November 19th).

via @siubaofong_stagelx

51. Seeing Elf the musical on opening night (November 21st). 

Buy tickets.

via @srcregan

52. Finally getting to go to the Distillery District Christmas Market.

via @stefansammy

53. Taking in the Calvacade of Lights (November 25th).