Urban utopia in the Annex

In the beating heart of Toronto lies a neighbourhood characterized by an intoxicating blend of charming eateries, independent and globally recognized retail outposts, and major art institutions that make this the notable cosmopolitan city the world has come to admire. Hard to believe it was once considered a suburb. The Annex, a historic neighbourhood—bordered by Bathurst Street to Avenue Road and Dupont Street to Bloor Street—draws visitors and residents alike with its plethora of attractions. It’s been over a century since Toronto expanded and The Annex shed its “suburban” past, and ever since, it has consistently drawn people looking for an urban neighbourhood rife with historic homes, parks, top schools and so much more.

“Transportation has had the greatest influence on the desirability of the Annex,” says Alex Corey, real estate agent and architectural historian at Heaps Estrin. “Toronto’s extensive streetcar network of the late 19th and early 20th century attracted the earliest residents,” while the arrival of the Bloor subway in the 1960s stitched the area into Toronto’s urban fabric. By mid-century, The Annex’s residents had established a somewhat utopian neighbourhood that was centrally located, well connected and deeply loved. It’s no wonder journalist and urban activist Jane Jacobs joined a community-wide opposition to the building of the Spadina Expressway, which would have fractured the neighbourhood, polluting it, and affected its superior walkability. Construction had begun in 1963, but their efforts led to a successful cancellation of the project in 1971. Later that decade, the new Spadina subway line opened, making the area even more attractive to new residents.

The Annex is equally known for its distinct architectural character. Architect Edward James Lennox defined the “Annex Style” as a combination of Romanesque and Queen Anne Revival styles, mixing rounded archways and conical rooftops with bay windows and decorative details. “[The Annex] also has fantastic examples of Georgian Revival, Edwardian, Tudor Revival and Craftsman-style homes,” says Corey. Whether you’re looking for a mid-century apartment or a large, single-family home, this neighbourhood offers a wide variety of residences with selling prices ranging from $630,000 to $8 million—the average selling price over the last two years was just over $3 million, Corey says. The only consideration is that private parking can be scarce, but residents can truly say they’re steps from it all.

Rachel Low, founder of book club and event series Readable, moved to The Annex in 2017. “It’s amazing because you can walk everywhere. You have access to so much,” she says. But the throughline for her is community: she’s on a first-name basis with her neighbours, joined the street group chat, and found an extensive community of artists and like-minded people who seek connection. “[Here] you’re in contact with people in a different way,” she says. “I’ve [met] a number of [people] at my coffee shop. It’s been a game-changer.”

Where to fuel up

Get ready to take on the day with a freshly brewed coffee and breakfast sandwich from First and Last Coffee Shop (346 Dupont St.). If you’d rather linger over a cappuccino and cornetto, stop by L’Espresso Bar Mercurio (321 Bloor St. W.), a family-run Italian café that’s been a neighbourhood staple for over 20 years. Stroll west and you’ll find Tiny’s General Store (80 Barton Ave.), where owner Chrys Nguyen serves coffee and snacks. She also stocks her shelves with a curated selection of housewares and prepared foods from other local businesses. Whether you need a quick bite or a catered spread for guests, Schmaltz Appetizing (414 Dupont St.) is a crowd pleaser. Chef Anthony Rose’s Jewish food shop remains one of Toronto’s best places to grab a bagel and the essentials that go with it, while Summerhill Market (1014 Bathurst St.) is a gourmet grocer with a bounty of prepared foods and specialty items.

Where to go

This one’s easy: start at Canada’s largest museum, the Royal Ontario Museum (100 Queens Park), where you can journey through time via their collection that counts over 18 million artworks and artifacts. The neighbouring Royal Conservatory of Music (273 Bloor St. W.) is a prestigious school for aspiring musicians of all ages and hosts an annual PLAY Day, with interactive activities and free performances in Koerner Hall. Down the street, fashion, craftsmanship and history intersect at the Bata Shoe Museum (327 Bloor St. W.) where special exhibits are complemented with curator talks and family-friendly activities. Meanwhile, Gathering Wild (1043 Bathurst St.) offers classes and workshops for kids that allow them to explore art, music and crafts of all kinds.

Where to shop

Expect an eclectic mix of retail, ranging from vintage boutiques to high-end housewares. Vintage clothing store Common Sort (444 Bloor St. W.) is all about the thrill of the find, whether that’s snagging something from Christian Louboutin, miu miu or adidas. Shoppers looking for modern interiors will love lifestyle boutique Hopson Grace (200 Dupont St.) that stocks ultra stylish furniture, serving pieces and accessories from luxe brands like Alessi, Ginori 1735, Mud Australia and L’Indochineur. To accent your interior styling, pick up individual stems or a unique arrangement from contemporary flower shop Flùr (1087 Bathurst St.). Bookworms will love to browse the seemingly endless shelves at BMV Books (471 Bloor St. W.) that boasts four floors of used novels, comics, movies and music.

Where to dine

Whether you’re craving comfort food or a critically-acclaimed dish, you’ll find it in The Annex. You can’t go wrong with Schmaltz Appetizing’s sister restaurant Fat Pasha (414 Dupont St.), known for its falafel, salatim platter and other Middle Eastern delights. For fresh Mexican fare and margaritas, head to Playa Cabana (111 Dupont St.), which is discreetly located on a residential stretch of Dupont Street. Le Paradis (166 Bedford Rd.) delivers French bistro standards like steak frites and moules à la marinière, along with an ever-changing list of specials, while the Michelin Guide-recognized MIMI Chinese (265 Davenport Rd.) is a slick, upscale venue for Asian specialties like shrimp toast and Hunan chili sea bass. And the chic, Michelin-starred restaurant Osteria Giulia (134 Avenue Rd.) offers a Northern Italian seafood-rich menu—try the octopus carpaccio or pasta with squid (you’re welcome). The focaccia di recco is also a must-try. - Erica Dutra