Rosedale's Way Into the Brick Works Winter Market Starts on South Drive

The Evergreen Winter Market comes back to the Brick Works for four Sundays, November 29 through December 20. Evergreen's own advice on getting there points to Rosedale. In its 2026 market FAQ, it suggests walking in from Castle Frank Station or Chorley Park, and it tells drivers to arrive 30 to 40 minutes before the 11 a.m. opening to get a parking spot.

Both walking routes start in Rosedale. One begins on South Drive and the other on Douglas Drive. Evergreen puts the southern route at 25 to 30 minutes. The free shuttle from Broadview Station leaves every 30 to 45 minutes, so a resident who sets out on foot can be in the valley in about the time a shuttle rider might spend waiting at the stop.

South Rosedale's route: Milkman's Lane

The City of Toronto describes Milkman's Lane as a 300-metre trail that runs from South Drive, near Craigleigh Gardens, down to the Don Valley trail network and Brick Works Park. The lane is short, but it feeds into a longer walk. Evergreen's Getting Here page lays it out like this:

1. From Castle Frank Station, walk north on Castle Frank Road, past Hawthorne Gardens.
2. Turn west on Elm Avenue and follow it to South Drive.
3. Walk north on South Drive past the entrance to Craigleigh Gardens. The Milkman's Lane trailhead is on the right.
4. Follow the trail downhill to the Beltline Trail, then head east, following the Moore Park Ravine signs, all the way to the Brick Works.

From most South Rosedale streets, the first two steps take care of themselves, since South Drive is close to home. Evergreen calls the descent "relatively gradual," and its directions include one warning that is especially useful once the leaves are down and the slope is wide open:

"Ignore all the little paths down the slope. Be patient! Watch for a maintained trail with a sign at the top of it."

The route you want is the maintained, signed trail, which the City lists at 300 metres.

North Rosedale's route: Chorley Park

The northern approach starts at Chorley Park on Douglas Drive. Evergreen's directions assume you are coming from the subway on the 82 Rosedale bus from Rosedale Station. A resident who already lives near the park can skip the bus.

Inside the park, walk east to the point where the black fence ends and the trail begins. Take the paved trail to the right and go down the stairs on the slope. At the bottom, stay on the pavement and take the lower branch where it forks. Near the end of the pavement, a path on the right joins the main trail. From there, take the Beltline Trail south to the Brick Works entrance.

Evergreen gives the Milkman's Lane walk a time but does not give one for this route, and it has stairs where the southern route has a gradual descent. That difference matters for anyone pushing a stroller or bringing a heavy bag home from the vintage tables.

Both routes end on the same valley trail, so check the posted signs at whichever trailhead you use. Last November, the Midtown Ravines Group reported that construction on the Mud Creek inlet restoration at the Brick Works was causing trail closures, with completion targeted for February 2026. The signs at the trailhead are the most current guide to which paths are open on a given Sunday.

The ravine route has one seasonal limit

Evergreen lists the Beltline Trail as a cycling route too, entered near Castle Frank Station. It also notes that the route "is generally impassable by bike in winter." So Rosedale cyclists need a different plan in December. Evergreen's other Rosedale bike route is Rosedale Valley Road, which runs east from Yonge Street off Aylmer Avenue, just south of Rosedale Station. There is a Bike Share Toronto station at the Brick Works for anyone who would rather not ride home uphill on their own bike.

That limit applies to wheels. Evergreen still lists both walking routes, and its winter market advice still recommends walking in from Castle Frank or Chorley Park.

How the other options compare on a market Sunday

Here are the other ways to get there, with the details Evergreen publishes for each:

A few shuttle details are worth knowing. You can download the MSL Shuttle Tracker app and enter the code EBW1 to see where the bus is and when it leaves next. The shuttle is wheelchair accessible, but there are three steps to board. Pets are not allowed, although service animals are welcome. For drivers, Evergreen says Bayview Avenue is signed "No Parking" and ticketed, and suggests calling 416-596-7670 to ask about parking on a particular day.

With a 26-person shuttle and parking that Evergreen says fills up quickly on weekends, the trail is the one option that doesn't depend on a seat or a parking space.

Which Sunday to go

According to Evergreen's Winter Market page, some things run every week and others only on certain dates:

• Every Sunday, 11 a.m. to 5 p.m.: the Ontario Vintage & Artisan Market, the Food Court, the Winter Lounge with live local performances, and the Art Hive, a free community art studio that uses recycled, thrifted, natural and donated materials.
• November 29 and December 6: the Winter Garden, with fire pits, s'mores and hot drinks.
• December 20, weather permitting: public skating in Koerner Gardens, with skate rentals on site.
• Select dates: festive workshops with partners including Rooks to Cooks and Let's Make It. These need registration.

Entry is pay-what-you-can, with a suggested $5 per person or $20 per family. On a walking day, the first two Sundays are the best pick. The Winter Garden fire pits are only on those dates, and they come at the end of a cold walk down, before the climb back up.

Families who want to walk the valley before the market opens can join Evergreen's Family Wander on Sunday, November 22, from 10 to 11 a.m. Registration is required, and the suggested donation is $20 per family.

The weekend before, on Roxborough Drive

A week before the Brick Works market opens, Rosedale has a holiday sale of its own. Rosedale United Church's Holly Berry Fair runs Saturday, November 21, from 10 a.m. to 4 p.m., and Sunday, November 22, from 11:30 a.m. to 4 p.m., at 159 Roxborough Drive. It has a Santa's Workshop for children, vintage and thrift markets, a range of vendors, and lunch on both days. All proceeds go to the Out of the Cold meal program at St. Luke's United Church, at Sherbourne and Carlton. The church also accepts donations of items for the thrift tables, the silent auction and the book sale before the fair.

On November 22, you can do both. The Family Wander ends at 11 a.m. in the valley, and the fair opens at 11:30 a.m. on Roxborough. Given how far apart the two are, most people will probably need a car or a cab to make that handoff.

Between market Sundays, the church has two evening events on its Christmas calendar:

• Monday, November 30, 7 to 8:30 p.m.: Women's Advent by Candlelight
• Tuesday, December 8, 7:30 to 8:45 p.m.: the Christmas Carol Concert & Sing-Along in the Sanctuary, with a brass band, pipe organ and the church choir

Both are at 159 Roxborough Drive. With the four market Sundays, that fills most of the weeks between late November and the solstice, and every event is either in Rosedale or a ravine walk away.

Over many seasons, Anita Springate-Renaud and her team have come to know Rosedale's trailheads, side streets and seasonal rhythms. If you would like to talk through what this part of the city offers, from Craigleigh Gardens to the valley below, Anita Springate-Renaud is glad to hear from you. You can find more on the neighbourhood on our Rosedale page and in our piece on Rosedale ravine living. Let's Connect.