Neighbourhood: Old Town and Moss Park
So, how old is Old Town? The area earned its name more than two centuries ago as Toronto’s first official neighbourhood. Its rich history is reflected in the charming 19th-century architecture, making it a great spot for both history buffs and aesthetes. Old Town is also home to one of the city’s most iconic landmarks: St. Lawrence Market. The nearby Moss Park neighbourhood, though small, is worth exploring for its colourful, vintage storefronts.
Walking perks
Bordered by Queen Street to the north and Front Street to the south, Old Town only spans from Church Street and Parliament Street; it being relatively contained (even if you include Moss Park, which encompasses Jarvis to Parliament, between Queen and Dundas) means you can cover a lot of ground during your amble. Plus, the old-school architecture is some of the best in town.
How to get there
Take the 75 Sherbourne bus from the Bloor line or hop off at King Station and walk a few blocks east. The King and Queen streetcar lines also run through the area.
Start your tour at the Cathedral Church of St. James (106 King St. E.). This soaring beauty is gorgeous inside (all that stained glass) and out (the record-breaking turquoise spire). Keep an ear out for the pealing bells.
Walk west along King, taking in all the beautiful historical buildings along the way: most of them maintain their original façade below, then stack new developments on top. Turn south down Leader Lane — check out the huge Guinness clock mounted on the side of Irish pub PJ O’Brien’s — and look left to admire the fun trompe l’oeil art on the back end of the famous Flatiron Building.
Stop #1: Berczy Fountain (35 Wellington St. E.)
This highly cute oasis is encircled with dog statues of all shapes and sizes, each looking skyward toward the coveted bone. (Peep the one cat, whose eye is, of course, trained on a nearby bird sculpture.) The double-hand sculpture on the west side of the park is also worth a look. The park is a lovely spot to sit and while away an hour or two, people-watching under the trees.
Hot tip: Head south on Church Street to view a real-life Banksy (4 Church St.) nestled right near street-level.
Stop #2: St. Lawrence Market (92 Front St. E.)
Skip the peameal and grab a succulent lobster roll from Buster’s Sea Cove instead (it comes with the crispest pickle in all Toronto). Then stock up for your next snackfest with Chocosol candied pumpkin chocolate bars and fresh cherry limeade from the St. Lawrence Juice Bar. Manotas is a must-visit for its plant-based Mexican treats, from a whole rainbow of juicy salsas to mouth-watering arepas.
Hot tip: Journey up to the second floor to the Market Art Gallery for fascinating rotating art exhibits and don’t forget to clock the expansive view of the market from the window.
Stop #3: Toronto’s first post office (260 Adelaide St. E.)
Head south to Adelaide Street East and admire the 19th-century architecture of the Bank of Upper Canada Building (252 Adelaide St. E.) and the De La Salle Institute Building (256 Adelaide St. E.) — plus stunning hibiscus flowers the size of your head — then duck into the city’s first postal outlet, which is still in operation today. You can also try writing your name with a quill, check out a model of Old Town, and learn about famous forgers. Pick up a Toronto postcard or two made by local artists as you leave.
Hot tip: Continue east down King to get a glimpse of the city’s future food stars hard at work through the giant window of George Brown’s culinary school kitchen (300 Adelaide St. E.); you can sample their budget-friendly goods inside at Chef on the Run (heads up: they often sell out early.).
Stop #4: Moss Park Espresso (185 Queen St. E.)
Look to your left into the alleyway just before Artik 314 (314 Adelaide St. E.) for a fabulous piece by one of Toronto’s most renowned graffiti artists, Elicser Elliott (the fact that it has remained untouched for 15 years is A Big Deal). Walk north to Queen and take a load off at Moss Park Espresso; indulge in homemade gelato or add an almond cookie (made in-house) to any drink for just 50 cents. Owner Joe is a real sweetie who will come out of the back to rhapsodize with you about his love of Toronto (if you ask nicely, he may even show you his very cool gelato machine).
Stop #5: Acadia Art and Rare Books (232 Queen St. E.)
The technicolour wares may be eye-wateringly expensive, but vintage decor shop Apartment (238 Queen St. E.) is still worth a stop for some fun, wouldn’t-it-be-nice window-shopping. (The block’s cheerily painted storefronts are also a real treat.) Double back to your last stop, the truly magical Acadia Art and Rare Books store, founded almost 100 years ago. You’ll feel like a character in a rom-com, browsing the towering shelves of stunning art books and vintage editions. (Shopcat pets optional.)
A local’s favourite spots
Kelsey Wilson, video producer at the Toronto Star and curator of torontostarchives on Instagram. I’ve lived in the area for 11 years and counting.
Why I love Old Town/Moss Park:
The Gooderham Building, St. Lawrence Market, Berczy Park — the list goes on. These places are tourist attractions for a reason. The neighbourhood sits in the heart of downtown but still holds onto a small-town charm. As a history buff, it’s a joy to live among such rich architecture.
I love being close to St. Lawrence Market, especially during off hours. The vendors are genuine — they know their regulars and treat them well. Berczy Park is great, but I think St. James Park is underrated.
From a practical standpoint, being within walking distance of Union Station is the gift that keeps on giving. And being near the lake means regular walks along the waterfront — something I never get tired of.
George Street Diner (129 George St.)
When anyone asks for a lunch or brunch recommendation, this is always my first choice. The food is consistently great, and the retro diner decor is an added bonus. The Irish owner, Ash Farrelly, is super friendly and has a great backstory. It’s always busy, but the wait is never long.
I order the Irish breakfast, of course, with their excellent homemade soda bread. You can even buy a make-it-yourself version, along with some imported Irish snacks at the register.
Hot tip: You can also order their soda bread ahead if you call in.
Triple A (138 Adelaide St. E.)
I never have a bad time at AAA. The esthetic is charmingly grungy in the best way. The staff is top-notch — and so is the playlist of late ‘90s and early-2000s punk-rock/emo hits. It’s also pet-friendly, which is a perk for dog lovers.
Shoutout to Lily, the MVP bartendress who once shared her playlist perfectly titled: “Songs I Got F—-ed to in My Volvo.”
Hidden Gems at the St. Lawrence Market
Family Food Market
A grocer on the northeast corner of the upper level. Their produce is always fresh and reasonably priced. I go here for fresh herbs — the selection is always twice what you’d get at a regular grocery store, and cheaper, too.
Alex Farm Products
A cheese shop on the southeast corner of the upper level. A cheesemonger there once recommended their Macedonian feta, and I haven’t bought any other kind since.
Domino Foods
A family-owned bulk store in the southeast corner on the lower level. The staff are super knowledgeable, and they carry items you won’t find at Bulk Barn. I have a few go-to’s, but lately I’ve been picking up their Callebaut chocolate and the olive oil they import from Rocca San Giovanni, Italy.
St. Lawrence Pizza & Ice Cream
Located next to Buster’s Sea Cove on the upper level. Ironically, I’ve never tried their pizza or ice cream. Their real specialty is a tomato, pesto, and fettuccine Alfredo combo pasta sauce. It might sound like Italian blasphemy, but I suggest you taste before you judge.
