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Morning

Begin your day with an espresso at Jet Fuel, 519 Parliament St. After your caffeine jolt, turn right and walk north to Wellesley St, then turn right again and walking east to take in the charming Victorian architecture. Note the strange animal and face carvings on No. 314. Explore the lanes running northward, including Wellesley Cottages, a courtyard tucked behind the street with seven gabled cottages. As you come to the end of Wellesley St, spend a few moments wandering through Wellesley Park, enjoying the view across the Don Valley.

Backtrack to Wellesley St and turn left onto Sumach St, its charming houses classic Cabbagetown. Note Second Empire-style No. 420–422, built in 1886, and the English cottage style of Nos. 404–408. Turn left at Winchester St; Necropolis Cemetery, Toronto’s oldest non-denominational graveyard, will be on the left. Peek into the chapel to admire the stained-glass windows.

Afternoon

For lunch, head back along Winchester St to Parliament St turning left to Carlton St, where you’ll find the Town Grill at No. 243.

After lunch, continue to meander the area’s compact streets – Metcalfe, Salisbury, and Sackville – before walking east to Riverdale Park and its Riverdale Farm . Across the street from the park’s northwest corner is cute Winchester Café, dispensing refreshments through a side window.

Morning

Begin at Sunset Grill, 2006 Queen St E, for breakfast. (The waffles are a local favorite.) Fortified, cross the street and meander toward the lake through Kew Gardens, noting the unusual circular path and rounded windows of Kew Williams Cottage, built in 1902, at the park’s south end. If you prefer cycling to walking, first check out Beach Cycles (1882 Queen St E) for equipment rental.

Reaching the boardwalk, turn right and follow it to the end, a 15-minute stroll. Look out for the paved path on the right; take it into Ashbridges Bay Park, where you can stroll along the waterfront, watching sailboats moor. The city view from the west side of the park is excellent.

For lunch, retrace your steps to Kew Gardens, then up to Queen St, for a famously good burger at Lick’s (No. 1960).

Afternoon

Spend the afternoon browsing the shops on Queen St, picking up at treat at The Nutty Chocolatier, No. 2179, to enjoy while taking a break at the serene sunken rock garden – Ivan Forest Gardens – at Queen St E and Glen Manor Dr.

Shopped out, snag a seat on Quigley’s patio (No. 2232) and relax with a refreshment. If you’re up for more walking, continue another 10 minutes east to the (see Greater Toronto) to stroll the grounds of this Art Deco gem and admire the view of the Scarborough Bluffs (see Bluffer’s Park) and Lake Ontario.

Morning

Start the day at the Gardiner Museum of Ceramic Art (see Gardiner Museum of Ceramic Art), taking 90 minutes to peruse the permanent collections and visiting exhibit. On your way out, pop into the gift shop to have a look at the unique crafts.

Head north to Bloor St and turn left, walking a half block to the iron gates of Philosophers’ Walk, beside the ROM (see Royal Ontario Museum). Take this charming footpath, which follows the course of the now buried Taddle Creek, exiting at Hoskin St in the heart of the University of Toronto campus. Wander south to the Late Gothic Revival Hart House, lunching at Gallery Grill on food that matches the impressive surroundings.

Afternoon

After lunch, poke around the stately common rooms and library of Hart House, noting the paintings throughout. Check out Canadian art at Justina M. Barnicke Gallery, too.

From Hart House turn right toward University College and some of the most historic buildings on campus. Stop by the Laidlaw Wing to visit the University of Toronto Art Centre . Just to the south, on King’s College Circle, is the 1906 Convocation Hall, with its Ionic-column-supported dome. Peek inside if the doors are unlocked.

From here, it’s only a couple of blocks’ stroll south and west to Chinatown. Indulge in a feast at Lee Garden (331 Spadina Ave).

Morning

Start at St. Jacobs Farmers’ and Flea Markets, admiring the handicrafts, collectibles, and foodstuffs of over 600 vendors. After stocking up snacks, walk across the parking lot to the Trolley Shop for a 75-minute horse-drawn trolley tour through Mennonite farm country (Apr–Oct).

After the tour, drive to the Visitor Centre at 1406 King St N; it features a short video on Mennonite history, photo exhibits, and a replica of a Mennonite Meetinghouse. Then, ready for lunch, head to Stone Crock (No. 1396), for a country-style buffet.

Afternoon

Drive east on County Road 17; in a few miles you’ll come to Road 22. Turn north to Route 86, then east on 86, watching for the sign to West Montrose. In this small town, look for the last remaining covered bridge in Ontario – called the kissing bridge by locals. The bridge crosses Grand River, a Heritage Waterway. Take Route 23 (turning into R21) north to charming Elora, 10 minutes away.

Once there, browse in the craft and antique shops and admire the old limestone buildings before walking to the Elora Gorge Conservation Area to swim, hike, and enjoy your picnic snacks by the water.

Next, it’s a short drive on Route 18 to Fergus, rich in Scottish history and late 19th-century architecture. Dine at the 1860s Breadalbane Inn (487 St Andrew St W).

Morning

Start at Commerce Court North (see Commerce Court North) to admire the stunning lobby. Walk west to Bay St and the TD Centre, noting the Wall and Chairs sculpture in the plaza (see Wall and Chairs) and Joe Fafard’s life-sized bronze cows lounging on the lawn behind 77 King St W.

Just around the corner at 234 Bay St is the Design Exchange (see Design Exchange). Explore it for an hour before enjoying a pan-Asian lunch at Kubo DX, on the first floor.

Afternoon

Zigzag your way to Simcoe Park, on Front St west of Wellington, and the luminous Anish Kapoor sculpture. A monument beside it honors city founders. Continue west along Front, past the CBC at No. 250, noting the Glenn Gould sculpture, in memory of the eccentric pianist. You’ll soon come to Sky-Dome, and The Audience, Michael Snow’s larger-than-life fans (see The Audience).

Turn left on Spadina Ave; crossing the bridge, look to your left to see Eldon Garnet’s memorial commemorating Chinese laborers who helped build Canada’s railroad. It’s five minutes to the lake and, just west on Queens Quay, Toronto Music Garden, in bloom spring to fall. Wander this oasis for an hour, then walk 15 minutes east to York Quay Centre to watch artisans at work and stroll the Photo Passage.

End the day with a steak dinner at Harbour Sixty (60 Harbour St), in the opulent former Harbour Commission building.