1 Cheering ‘til we’re hoarse as the Toronto Maple Leafs take to the ice.
2 The monumental, cinema-inspired paintings of Julian Schnabel on display at the Art Gallery of Ontario.
3 Picking up a hefty new hardcover from Ben McNally Books.
4 Seeking inspiration from the Dalai Lama, who addresses the Rogers Centre on October 22.
5 Quirky Canadiana products at the Drake General Store—these are souvenirs even locals want to collect!
6 Welcoming back another cultural landmark—the Sony Centre for the Performing Arts has now reopened.
7 The super-sleek environs of The Room at The Bay—lucite chairs and sculptural mobiles alongside designer clothes.
8 Giving a standing ovation to the cast of Soulpepper Theatre’s Death of a Salesman.
9 The sophisticated yet unfussy nibbles at Origin.
10 Interacting with art all night long during Nuit Blanche.
11 Walking down bustling Yonge Street—Toronto’s best known artery.
12 Spotting literary icons at the International Festival of Authors, from October 20 to 30.
13 Grabbing a slice of pumpkin perfection from Wanda’s Pie in the Sky.
14 Ontario’s bountiful autumn harvest, laid out by merchants at the St. Lawrence Market.
15 Learning about fine art from top British critic Edward Lucie-Smith.
16 Living a little greener thanks to Planet in Focus, Toronto’s international environmental film festival.
17 Nodding along to the romantic hits of Stars—the Canadian band makes Massey Hall audiences swoon on October 23.
18 Refreshing your skin with a steam room session at Hammam Spa.
19 Being undead on October 23 for the Toronto Zombie Walk at Trinity Bellwoods Park.
20 Experiencing a taste of heaven at the Toronto Chocolate Festival, starting October 22.
21 Enjoying the breeze off of Lake Ontario while strolling along the Harbourfront.
22 Ending a meal at Marben with a decadent, super-chocolatey ice cream sandwich.
23 Picking up sumptuous leather accessories from Roots.
24 The charming Gaelic signs at long-standing Irish pub Dora Keogh.
25 Busting a gut at Massey Hall with Asian-American comedienne Margaret Cho—she cracks jokes on October 22.
26 The near-perfect acoustics of Koerner Hall, the performance venue of the esteemed Royal Conservatory (273 Bloor St. W., 416-408-0208).
27 After-work merriment fueled by specialty sake cocktails at Ki Modern Japanese + Bar.
28 Warming up with a bowl of orange and ginger carrot soup from Kalendar.
29 Photographing the beautiful orange, yellow and red leaves as fall arrives in High Park.
30 A bespoke suit from Harry Rosen—the perfect fit for any gentleman.