Two Days In Midtown Toronto: A Thanksgiving Itinerary

Whether you’re entertaining this Thanksgiving, looking for ways to spend your own weekend, or want to explore a new neighbourhood, we have the perfect itinerary for Thanksgiving weekend in Midtown Toronto. This itinerary takes the guesswork out of Saturday and Sunday, so you can focus on enjoying your time instead of planning.

Midtown Toronto Thanksgiving Itinerary Overview

Saturday: Explore a year round farmer’s market, step back in time at a historic mansion, take a self-guided public art walk, and enjoy local restaurants.

Sunday: Fill up at the deli, leaf through secondhand books, explore a hidden ravine, and take in fall colours.

Midtown Itinerary: Saturday

Today is all about history and art in Midtown Toronto.

Morning

Start your day at a local favourite, Mary Be Kitchen. The weekend brunch menu is guilt-free with all the flavour, offering dishes like smashed avocado with a twist and perfectly poached eggs with roasted sweet potatoes. Before you leave, grab a hot drink for the road like an apple cider or lavender latte.

Catch the westbound St. Clair streetcar at Yonge + St. Clair and ride it to Christie where you’ll hop off and make the short walk down Christie St. to Wychwood Barns.

Wychwood Barns is a community cultural hub inside a repurposed streetcar repair facility from 1921. Now it’s home to one of Toronto’s only year round farmer’s market, The Stop. Open 8am – 1pm every Saturday, this market features local Toronto vendors selling everything from cozy knit toques to cute tote bags, tasty fall pies and jam you’ll come back for.

Spend the rest of the morning moseying around the market, picking up treats, and supporting local businesses and producers as you go.

Afternoon

When your tote bag is full of goodies, make your way east on foot through the leafy Hillcrest neighbourhood. As you walk you’ll notice the houses getting bigger and fancier before reaching the mansions around Austin Terrace and Casa Loma, a grand castle-style mansion located a few steps from your next stop, Spadina Museum.

This beautiful museum is a historic mansion from the heyday of 1930s Toronto. Step back in time to when the affluent Austin Family occupied the home for four generations starting in 1866, see how they lived and what it would have been like for those who served them.

Expect lush gardens, fabulous furniture, and sweeping wooden stairs that ooze opulence. This is the sort of place where you can practically still smell the gin and hear the jazz. Admission is free by guided tour only. Tours run every Saturday, hourly from 11:15am – 3:15pm, and one final tour at 4pm. There are no reservations, just aim to arrive about 10 minutes before the tour you’d like to take.

When you’re ready make your way back toward Yonge + St. Clair on a self-guided art crawl. Head to St. Clair Ave. W and go east. Stop at the large Sir Winston Churchill Park on the corner to snap a few pictures of the CN Tower in the distance.

Cross to the north side of St. Clair Ave. W where you’ll find the Timothy Eaton Memorial Church, a neo-gothic church with a 100-foot bell tower. Continue on to Glenn Gould Park to see the 1929 Peter Pan Statue. This statue is one of seven casts of the original sculpture commissioned by J.M. Barrie, the creator of Peter Pan, which sits in Kensington Gardens in London, England.

Crossing to the south side of St. Clair, head into the Longo’s at Imperial Plaza. This protected building was once the home of the Imperial Oil company and the grand marble lobby harkens back to their success. On the back wall, split between the LCBO on the left and Longo’s on the right are the The Story of Oil murals by Canadian artist R. York Wilson.

Just next door you’ll see a sculpture that’s hard to miss, Toronto Man also known as Condo Man sits just off the sidewalk. A businessman standing on coloured blocks, holding a condo building. This sculpture is a conversation piece and was created using updated medieval art techniques. It is one of the best known public artworks in Midtown Toronto.

In the very next building you’ll find Reclining Torso, a bronze sculpture by Canadian John Fillion. The sculpture is right outside the building and there are some benches to sit and visit for a while.

You’ll probably see the last stop on the art walk before you reach it. The massive eight storey black and white mural by British artist Phlegm is on the wall above Mary Be Kitchen. Stop and take a look. Do you recognize any buildings? Can you spot the CN Tower you just photographed?

Evening

This evening, have dinner in the neighbourhood. Union Social Eatery is another local favourite with a menu that can please any palate. Try their famous almond-crusted chicken fingers or order the firecrackers for a unique fusion appetizer you can share.

Midtown Itinerary: Sunday

Slow down today and dive into the nature around Yonge + St Clair.

Morning

Head to Zelden’s Deli and Desserts for one of the best brunches in the neighbourhood. Opt for one of their stuffed deli sandwiches or choose a special from the brunch menu, like the smoked meat benedict.

When you’re ready, take a stroll up Yonge St. and pop into Book City. Spend some time browsing the shelves and pick up your next read for a fraction of the price of the big stores.

Afternoon

From here, head to David A. Balfour Park. This park is a hidden haven just steps from Yonge + St. Clair and is the gateway to an even more magical place, the Vale of Avoca ravine. Stop to read the historical plaques at the entrance to learn about how under the grassy expanse is the Rosehill Reservoir. This reservoir has been storing drinking water for the residents of Midtown Toronto for over 100 years and you can find a tribute to that in the form of the giant metal Water Molecule sculpture on the edge of the park.

Fill your water bottle at the fountain and make your way to the Avoca Ave. access point of the beautiful Vale. As you head down the slope you’ll enter a whole other world of towering trees and the babbling Yellow Creek. This was once an ancient hunting ground for the Indigenous before becoming a Victorian summer destination and eventually turning into the hidden hiker’s paradise we have today, right in the middle of Midtown.

When you reach the ravine floor, turn left to head north. The ground can be uneven so watch your step as you take in the changing colours of the trees and see squirrels springing about. Shortly, you’ll reach the St. Clair Viaduct, a huge triple arch bridge crossing the ravine overhead.

As you continue along the trail you’ll reach an open gate. This is the entrance to the gorgeous and historic Mount Pleasant Cemetery. This beautiful cemetery is also an arboretum with hundreds of species of trees, many of them marked with identifying plaques.

This is one of the most stunning places in Toronto to view fall colours so take time to explore the winding paths. You can also find some historic graves in this cemetery. The Massey Mausoleum, belonging to the famed Massey Family, in the middle of the cemetery was designed by E.J. Lennox, the same architect who designed Old City Hall and Casa Loma.

You can also find the Eaton Family Crypt, the family behind the Eaton’s empire, William Lyon Mackenzie King’s grave, the longest serving Canadian Prime Minister, and the jaw-dropping The St. Andrew’s Society Monument that looks like something from another place and time entirely.

Evening

This evening, try something new by having dinner at El Inka. This Peruvian restaurant serves elevated yet authentic cuisine most people wouldn’t have the chance to try. The staff can help guide you through the menu as you discover your new favourite Midtown restaurant.

Thanksgiving is here, so enjoy a slow evening with loved ones in Midtown Toronto.