Literary City Guide | TORONTO, CANADA

Before the real city could be seen it had to be imagined,
the way rumors and tall tales were a kind of charting.
— Michael Ondaatje, In the Skin of a Lion

Tour Guide: Jaime Maddalena

Jaime is a photographer and former poetry zine writer. She also adores writing letters. Send More Mail is her vintage postage stamp shop which was created to encourage others to write letters the old fashioned way. After twenty-two years in the city, Jaime has recently set off on some extensive travels. You can follow her adventures here(Photos by Jaime Maddalena.)


Relationship to Toronto: At 17 I moved to the city for school. I studied photography at a downtown university where I met Joseph. We got married a few years later and have been shooting and traveling together ever since.

Writer you’d like to invite to dinner: Barbara Kingsolver

Chef you’d like to prepare the meal: Chris Bianco

Writing soundtrack: The local jazz station.

Pen or Pencil: Pencil

Coffee or Tea? Coffee

Paperback or Hardback? Paperback

Good Reads


Type Books. My go-to shop for new novels, travel guides, even stationery. After you find your next read, take it across the street to Trinity Bellwoods park. (Fingers crossed you find a shady bench!)

Good Egg. Whenever I’m doing groceries in Kensington Market I pop into Good Egg for cookbooks galore, plus extra-cute and practical (new cast iron pan?) kitchenware. 

Swipe Design. A bit of a hidden gem, Swipe is a design book store tucked inside 401 Richmond. Besides some of the most beautiful hardcovers out there, the Moleskine collection is fine. (Moleskines are my preferred notebooks for journaling.)


Fort York Library. One of the newest additions to the 100 branches of the Toronto Public Library system. Floor-to-ceiling windows make browsing beautiful. I always seem to come home with a new staff-suggested read that delights.

High Park Library. If you’re looking for a quiet tiny reading nook, this branch has just that. A bit of a secret, look for a little flight of stairs on the second floor to find it! This converted church has high ceilings, a great magazine collection and it’s right in the middle of the west end Polish neighborhood. Tuck into a deli or cafe afterward for post-reading snacks.

Lillian H. Smith Library. I can’t bike past here without stopping. Hosting knitting circles and paper making classes this downtown branch makes me love the community vibe in such a big city. P.S. The collection of early 1900s children’s books is sure to please! 


The Word on the Street. This celebration of all things literary takes place every September. Why not take in a reading or two on the shores of Lake Ontario? 

The International Festival of Authors. Since the mid-70s IFOA has been celebrating words and ideas. This October event features poetry readings, conversations and meet-and-greets with your favorite novelist.


Little Free Libraries. Toronto is filled to the brim with Little Free Libraries. A great way to donate books and find surprising gems. (My latest includes a collection of Julia Child’s letters and a 1961 Nancy Drew mystery.)

Kid Icarus. Stationery, local crafts and print shop all in one.  

Black Coffee and Pie. My friend Ivy hosts this speaker series at the Drake Hotel. Authors and chefs speak, do a Q + A, then everyone eats (free) pie.

Good Eats


Gloryhole Doughnuts. If you’re feeling like a PB + J in doughnut form, this is the place to go. (Side note: Coffee pairs up extremely well with the toast and butter doughnut.)

Sud Forno. This Queen West café’s zeppola (think cream puff with dark cherries) make me very, very happy. And their cappuccino is A+.

Via Mercanti. A near-perfect espresso can be had at this pizzeria. Not really a coffee shop, but a pizzeria with excellent coffee!