🍂 Fall Walk: From Rosedale to Cherry Street 🌿
A Fall Walk Through Some of Toronto's Most Interesting Neighbourhoods
Looking for a walk that gives you a little bit of everything?
We'll start in Rosedale, make our way through Cabbagetown and Regent Park, wander through the Distillery District, stop at Biidaasige Park, and finish with a well-earned meal at Cherry Street Bar-B-Que.
Along the way, we'll see some of the city's oldest neighbourhoods, newer communities, historic architecture, green spaces, and some pretty great views.
It's a longer walk, but the route is more about exploring Toronto together than trying to finish as quickly as possible.
📱 Don't forget to join our WhatsApp Group – [CLICK HERE](https://chat.whatsapp.com/H59mSCbsAi018gYANrKAnc)
*
🚶♂️ What We'll Do
We'll meet outside Rosedale Station and begin our walk through Rosedale Valley, following the tree-lined route toward Cabbagetown.
Along the way we'll:
• Walk through Rosedale Valley 🌳
• Explore the historic streets of Cabbagetown
• Pass through Regent Park
• Wander through the Distillery District
• Stop at Biidaasige Park
• Take in the fall scenery and city views
• Finish at Cherry Street Bar-B-Que 🍖
The walk includes a long set of stairs, so while this isn't a difficult hike, you should be comfortable walking for several hours and keeping up with the group.
*
🏙️ A Little Toronto History Along the Way
This walk takes us through several very different parts of Toronto.
In Cabbagetown, we'll pass beautifully preserved Victorian homes and streets that reflect the neighbourhood's long history, including its Irish roots.
We'll then make our way through Regent Park, one of Toronto's most historically significant communities, where older social housing has been joined by new housing, arts, and community spaces.
From there, we'll head into the Distillery District, with its cobblestone streets and historic red-brick buildings.
We'll also stop at Biidaasige Park, whose name means *“the sun is shining”* in Anishinaabemowin.
It's a lot of Toronto in one walk.
*
🍺 The Keating Channel Pub & Grill
We'll finish our walk at The Keating Channel Pub & Grill, right on the Keating Channel.
There's a bit of history behind this stop. The pub struggled during the massive Port Lands construction, when road closures and the relocation of the Cherry Street bridge made the area difficult to reach. With the Port Lands now transformed and Biidaasige Park open, people are rediscovering this part of the city — and the pub is getting a second chance.
After exploring the new park and the transformed Port Lands, we'll finish at one of the neighbourhood's old survivors: a casual waterfront pub with a patio overlooking the Keating Channel.
*
☀️ Weather & Expectations
This is a long urban walk, not a difficult hike, but you should be comfortable being on your feet for several hours.
There is a long set of stairs along the route.
Please wear comfortable walking shoes and dress appropriately for the weather.
*
🧢 Meetup Details
📍 Meetup Location: Outside Rosedale Station
🫎 Look for me in my Moose Hat!
⏰ Meetup Time: 11:00 AM sharp
I will only wait 5 minutes.
Early is on time. On time is late.
🏁 End Point: Cherry Street Bar-B-Que
*
🎟️ Meetup Fee
$5 cash in person or e-transfer
📧 mathewmaclean@hotmail.com
This fee helps support the group and allows us to continue organizing events throughout Toronto.
*
🎒 What to Bring
💧 Water
👟 Comfortable walking shoes
🥪 A snack
🧴 Sunscreen
🧥 Weather-appropriate clothing
*
🌈 Who Is This For?
This walk is great for:
• People who enjoy exploring Toronto
• Anyone who likes history and architecture
• People looking for a longer social walk
• Anyone who wants to discover neighbourhoods they might not normally visit
• People who enjoy stopping for food at the end
• Anyone who wants to spend a Sunday exploring the city with other people
The destination isn't really the point.
It's the people you meet along the way.
You're welcome to…
