The eastern part of Toronto is a region of contrasts. Some of the city’s grandest old mansions remain along the stately streets of Jarvis and Sherbourne, though many of these homes were abandoned for years and have only in the past few decades undergone renovation and gentrification. The same is true of Cabbagetown, originally a working-class Irish immigrant neighborhood, where Victorian rowhouses and cottages have been transformed into an upscale neighborhood of urban professionals. There are many historic sights in the area and a vibrant streetlife throughout Toronto’s east side, thanks to the lively gay village along Church Street, the Greek and Macedonian enclave of The Danforth, and the fresh-food destination of St. Lawrence Market. To the south, a complex of Victorian buildings has been converted into the Distillery Historic District, one of the city’s newest shopping and entertainment destinations.

Don River

Named by the lieutenant-governor of Upper Canada, John Graves Simcoe, after a stream in Yorkshire, England, the Don River is one of the city’s defining natural features. Flowing just east of downtown into Lake Ontario, the river and its steep valley cut a swath through the city. While industrial use of the river, particularly at its southern end – where its meandering course is channeled into an abrupt right turn – have degraded the water, recent naturalization projects have started the long process of restoring the Don Valley to ecological health. The ribbon of connected greenspaces following the Don’s course means that you can hike and cycle along bike paths for hours right in the center of the city and encounter few signs of civilization.


  1. St. Lawrence Market

    Farmers sell fresh produce and baked goods from seasonal stalls in the north market on Saturdays, with many specializing in organic food. In the vibrant south market, open Tuesday to Saturday, permanent vendors sell everything from fresh bread and produce to seafood, meats, and cheeses. The south building served as City Hall in the mid- to late 1800s (see St. Lawrence Hall).

    Vegetables at St. Lawrence Market
  2. Distillery Historic District

    This Victorian industrial district is now one of the city’s most interesting and picturesque. Pedestrian-only cobblestone streets lead past old warehouses and historic factories stunningly preserved and renovated to house galleries, restaurants, performance venues, and specialty shops .

    Glass artwork, Ainsley Gallery
  3. The Danforth

    Linked to downtown by the 1918 Prince Edward Viaduct, which spans the Don River Valley, The Danforth has been called home by the city’s thriving Greek and Macedonian communities since the 1950s. In early August, the weeklong Taste of The Danforth street festival is a smorgasbord of tasty treats and live entertainment.

    Sidewalk café, The Danforth
  4. Cabbagetown

    One of Toronto’s earliest subdivisions, dating to the 1840s, this district remained a working-class community well into the 1970s. Many of the cottages and Victorian homes have since been renovated, and it is now an upscale residential enclave that makes for a pleasant stroll. On the east side is Riverdale Park and its delightful Riverdale Farm. Across the street, on the grounds of the Necropolis Cemetery, is a chapel built in 1872, a Gothic Revival treasure. At the north end of Cabbagetown, St. James Cemetery, Toronto’s oldest, has many beautiful crypts.

    Cabbagetown cottage
  5. Mackenzie House

    This Greek Revival rowhouse, built in 1858, was the home of Toronto’s first mayor, William Lyon Mackenzie, who returned here after being granted amnesty for his leading role in the failed Upper Canada Rebellion in 1837. Now a period museum, it features a recreated printshop and a gallery with changing exhibitions. It is rumored to be haunted.

    • 82 Bond St

    • open Jan–Apr: noon–5pm Sat–Sun; May–Sep: noon–5pm Tue–Sun; Sep–Dec: noon–4pm Tue–Fri, noon–5pm Sat–Sun

    • Adm

    Mackenzie House
  6. Church Street

    The hub of Toronto’s Gay and Lesbian Village, Church Street from Carleton Street to north of Wellesley Street, is vibrant day and night. Bars and restaurants cater to an out crowd, and specialty shops, such as those selling body wear, abound. The general vibe is pink and proud and it’s no wonder that the popular TV show Queer as Folk, made in Toronto, is often filmed on location at Church Street. Pick up a copy of the free bi-weekly newspaper Xtra!, available at most shops on the street, for listings of everything the village has to offer.

  7. Allan Gardens

    This large park embodies the contradictions of the downtown-eastside: It is both grand and gritty. Best explored during the day, the gardens, which first opened in 1860, contain a delightful glass-and-metal conservatory complex consisting of six greenhouses, each with a different climate zone, built in 1910. Inside, the exuberant displays of seasonal and permanent greenery and flowers delight the senses.

    Conservatory, Allan Gardens
  8. Toronto’s First Post Office

    This working post office and museum opened in 1833 and is the only surviving example of a British-era post office in Canada. Here, you can write a letter with a quill pen and have it stamped with a distinctive cancellation mark: “York-Toronto 1833.” There is also a topographic model of 1830s Toronto, period furniture, and 19th-century reproduction ink wells and sealing wax. The library, housing an extensive archival collection of postal-related materials, is open by appointment only, but admission to the museum is free for self-guided tours.

    • 260 Adelaide St E

    • Open 9am–4pm Mon–Fri, 10am–4pm Sat–Sun

    Toronto’s First Post Office
  9. Todmorden Mills Heritage Museum & Art Centre

    The collection of late 18th-century buildings that makes up this museum complex impart the feel of a historic village. Fine examples of the original industrial architecture, such as a paper mill, are peppered throughout the site. Two houses – the 1797 Terry Cottage and 1800s Helliwell House – have been restored with period furnishings. The 1881 Don Train Station will delight rail buffs. The Brewery Gallery exhibits pieces related to the site. A wildflower preserve bursts with trilliums in spring, and trails offer nature lovers lots of wildlife spotting opportunities, but be prepared for deep snow in winter.

    • 67 Pottery Rd

    • Museum complex open May–Sep: 11am–4:30pm Tue–Fri, noon–5pm Sat–Sun

    • Adm

    • Grounds open year-round

    Todmorden Mills
  10. Don Valley Brickworks

    The smokestack is just one of the historic features that remain at this once-thriving industrial complex, which opened in 1889 to manufacture bricks for local buildings using clay found on site. Some 100 years later, the quarry has been returned to nature as a park with ponds and meadows .

    • 550 Bayview Ave

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