Published 30 October 2026 · By Jatin Dua, Broker of Record, RE/MAX Quantum Realty
My top five for the 2026 holidays are the 6 December carols and 9 December Holiday Season Market at Montgomery’s Inn (4709 Dundas St. W.), the Etobicoke Centennial Choir’s Halls of Joy concert on 5 December, Neilson Park Creative Centre’s holiday craft sale on 21 November, skating on the Colonel Samuel Smith Park figure-eight trail, and the Junction’s Window Wonderland (27 Nov–31 Jan). The order is my judgement, not an official ranking.
How I chose these five
Every pick here has a 2026 date, or a confirmed 2026–27 season, on an official or first-party page. A lot of well-loved Etobicoke traditions had not posted this year’s dates by the end of October, and I left those out rather than guess.
I looked for a spread: a historic venue, a concert, a craft sale, an outdoor activity and one light display. Four are in Etobicoke. The fifth, the Junction’s Window Wonderland, is just east of the Humber, and I included it because it is the best-documented holiday light display I could confirm for this season near Etobicoke.
I also favoured events that are free or low-cost and easy to reach from Etobicoke’s residential streets, because that is how most families actually spend December.
1. Holiday season at Montgomery’s Inn
What it offers
Montgomery’s Inn is a City-run historic site at the corner of Dundas Street West and Islington Avenue, and it is the most natural holiday stop in central Etobicoke. General admission is free, and the City lists it as open Wednesday to Sunday, 11 a.m. to 4 p.m.
The City’s Exhibits & Events calendar lists a free Carol Sing-Along with the Inn’s Music Studio students on Sunday, 6 December 2026, at 1 p.m. (reservations required), an adults-oriented evening of Holiday Season Carols in the Tavern later that day at 5 p.m. (ticketed), and a once-a-year Holiday Season Market with local craft and artisanal vendors on Wednesday, 9 December 2026, from 2 p.m.
What it means for buyers and renters
For buyers looking at the streets around Dundas and Islington, a free museum with a weekly market and seasonal programming is a real neighbourhood asset. It gives the area a sense of community that is hard to measure but easy to feel.
It is also on the TTC: the City suggests Islington station on the Bloor-Danforth subway, then a short walk north or the 37 Islington bus. That makes it a car-free outing for condo and rental households near the subway.
Practical notes
- Address: 4709 Dundas St. W.
- Parking: free lot, entered from Montgomery Road, one block east of Islington.
- Accessibility: the entrance has four stairs and uneven surfaces; the City’s accessibility line is 416-394-8113.
- Weekly market: the Inn’s farmers’ market runs Wednesdays, 2 to 6 p.m., per the City’s page.
- Fees: the City notes that some exhibitions and events carry a separate charge, which is shown on each listing, so check before you book the tavern evening.
2. Halls of Joy with the Etobicoke Centennial Choir
What it offers
Halls of Joy is the Etobicoke Centennial Choir’s December concert, on Saturday, 5 December 2026, at 7:30 p.m. at Humber Valley United Church. It opens the choir’s 2026–27 season, which the choir is billing as its 60th; it has been singing since 1967.
The programme is Baroque and festive: Bach’s Cantata No. 140 (Sleepers Awake), Galuppi’s Magnificat in G and Buxtehude’s Das neugeborne Kindelein, performed with a period Baroque orchestra, plus traditional carols and an audience sing-along.
What it means for buyers and renters
Community choirs and church concerts are part of what makes established Etobicoke neighbourhoods feel settled. If you are new to the area, a concert like this is an easy way to meet neighbours who have been there for decades.
The church sits on Anglesey Boulevard in a quiet residential part of central Etobicoke, close to Humber Valley Park. It is a good example of the local institutions that sit within walking distance of many detached-home streets here.
Practical notes
- Venue: Humber Valley United Church, 76 Anglesey Blvd.
- Tickets: the choir sells a three-concert season pass for $90, which it says saves $15 over single tickets; free children’s seats are reserved through the concert ticket links.
- Ticket line: 416-779-2258.
3. Holiday Handmade Art and Fine Craft Sale at Neilson Park Creative Centre
What it offers
Neilson Park Creative Centre’s holiday sale is on Saturday, 21 November 2026, from 10 a.m. to 4 p.m., with work from more than 60 local artists and artisans. Admission and parking are free.
The organizers list paintings, fibre art, scarves, hats, quilts, calligraphic artwork, jewellery, sculptures and wood carvings. It is an early-season sale, which is useful if you want handmade gifts without the December crush.
What it means for buyers and renters
A community arts centre with classes, exhibitions and seasonal sales is a quiet strength of central-west Etobicoke. It is the kind of amenity families and retirees both use, and it adds to the appeal of nearby streets.
If you are comparing neighbourhoods, ask whether there is an arts or community centre within a short drive that runs programs for children and adults. Neilson Park is a good benchmark for what that looks like.
Practical notes
- Address: 56 Neilson Dr.
- Doors: open at 9:50 a.m., per the event listing.
- Before you go: the free Eventbrite listing showed as sold out when I checked on 30 October 2026, so confirm entry arrangements with the centre.
4. Holiday skating on the Colonel Samuel Smith Park trail
What it offers
A December skate on the figure-eight trail in Colonel Samuel Smith Park is a lakeside holiday tradition for many south Etobicoke families. The City describes it as the city’s first ice skating trail, next to the Power House Recreation Centre.
The City says outdoor artificial ice rinks typically open in late November and that drop-in skating is free. Its Skate Lending Library van, which lends skates, helmets and skating aids at no cost and with no reservation, begins visiting rinks on 20 November 2026.
What it means for buyers and renters
For buyers weighing south Etobicoke, a lit skating trail within walking distance is one of the area’s best winter perks. It turns the lakeshore into a place you use in December, not just in July.
It is also a popular spot, so streets right by the park can see more parking on winter weekends. Visit at a busy time before you commit to a nearby home.
Practical notes
- Address: 3145 Lake Shore Blvd. W.; the trail is beside the Power House Recreation Centre, 65 Colonel Samuel Smith Park Dr.
- Hours: the City posts winter drop-in times on the park’s location page once the season opens.
- Season: the City had not posted a 2026–27 opening date for this trail when I checked.
5. Window Wonderland in the Junction
What it offers
Window Wonderland is a free, self-guided winter art walk that runs from 27 November 2026 to 31 January 2027 along Dundas Street West in the Junction. This is its seventh season, created by the Junction BIA with Artivive.
This year there are 32 augmented-reality installations: 20 new storefront windows and 12 year-round wall murals, under the theme “Movement + Glimmers”. You view the animations by scanning the windows with the free Artivive app, and it works day or night.
What it means for buyers and renters
It is not in Etobicoke, but it is a short trip east across the Humber for anyone in east Etobicoke, and it pairs well with an early-evening dinner on the strip. It is also a good look at what an active business improvement area can do for a main street in winter.
When you compare neighbourhoods, look at how much the local BIA programs its strip outside summer. Year-round activity is a sign of a healthy main street, and that tends to support nearby home values.
Practical notes
- Location: storefront windows and murals along Dundas St. W. in the Junction.
- Cost: free.
- What you need: a phone with the free Artivive app.
The five at a glance
| Pick | Where | 2026 date | Cost |
|---|---|---|---|
| Montgomery’s Inn holiday programs | 4709 Dundas St. W. | Carols 6 Dec; Holiday Season Market 9 Dec | Sing-along and market free; tavern carols ticketed |
| Halls of Joy concert | 76 Anglesey Blvd. | Sat 5 Dec, 7:30 p.m. | Ticketed; $90 season pass |
| Neilson Park holiday craft sale | 56 Neilson Dr. | Sat 21 Nov, 10 a.m.–4 p.m. | Free |
| Colonel Samuel Smith skating trail | 3145 Lake Shore Blvd. W. | Season typically opens late Nov | Free |
| Junction Window Wonderland | Dundas St. W., the Junction | 27 Nov 2026–31 Jan 2027 | Free |
What this means if you’re buying or selling in Etobicoke
December is a good month to judge a neighbourhood, because you see how it lives when the patios are closed. Look at what is within walking distance: a museum, a church hall, an arts centre, a rink.
In central Etobicoke, the streets around Montgomery’s Inn, Humber Valley United Church and Neilson Park Creative Centre all have long-running community institutions close by. In south Etobicoke, the Colonel Samuel Smith Park trail is the winter anchor.
If you are selling, holiday-season showings can work in your favour when the street is lit and the community calendar is busy. Mention nearby year-round amenities in your listing, accurately and without overstating distances.
If you are buying, take a winter evening walk around any street on your short list. You will learn more about lighting, parking and how lively the area is than any summer photo can tell you.
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Frequently asked questions
What Christmas events are on at Montgomery’s Inn in 2026?
The City’s events calendar lists a free Carol Sing-Along with the Music Studio on Sunday, 6 December 2026, at 1 p.m. (reservations required), Holiday Season Carols in the Tavern that evening at 5 p.m. (ticketed, intended for adults) and a Holiday Season Market on Wednesday, 9 December 2026, from 2 p.m. The Inn is at 4709 Dundas St. W.
When is the Etobicoke Centennial Choir Christmas concert in 2026?
Halls of Joy is on Saturday, 5 December 2026, at 7:30 p.m. at Humber Valley United Church, 76 Anglesey Blvd. The programme includes Bach’s Cantata No. 140, Galuppi’s Magnificat in G and Buxtehude, with a Baroque orchestra, carols and a sing-along. A three-concert season pass costs $90.
Is there a holiday craft sale in Etobicoke in November 2026?
Yes. Neilson Park Creative Centre, 56 Neilson Dr., holds its Holiday Handmade Art and Fine Craft Sale on Saturday, 21 November 2026, from 10 a.m. to 4 p.m., with more than 60 local artists and artisans. Admission and parking are free.
When is the Lakeshore Santa Claus Parade in 2026?
I could not find a 2026 date on an official page as of 30 October 2026, so I have not listed it. The parade’s older web page lists a 2015 date and no current details. Check the organizers’ channels in November before planning around it.
Where can I see holiday window displays near Etobicoke?
The Junction’s Window Wonderland runs from 27 November 2026 to 31 January 2027 along Dundas Street West. It has 32 augmented-reality installations, 20 storefront windows and 12 murals, viewed through the free Artivive app. It is free and self-guided, day or night.
Sources
- Montgomery’s Inn — City of Toronto
- Exhibits & Events calendar — Toronto History Museums, City of Toronto
- Current Season — Etobicoke Centennial Choir
- Holiday Handmade Art and Fine Craft Sale — Neilson Park Creative Centre on Eventbrite
- Colonel Samuel Smith Park — City of Toronto
- Public Leisure Skating — City of Toronto
- Skate Lending Library — City of Toronto
- Window Wonderland 2026 — The Junction BIA
Related reading
- Top 5 Outdoor Skating Rinks in Etobicoke (2026–27)
- Top 5 Tobogganing Hills in Etobicoke & West Toronto (2026–27)
- Top 5 Holiday Markets in Toronto’s West End (2026)
- Top 5 Events in Etobicoke
About the author — Jatin Dua, Toronto and GTA real estate broker
I am Jatin Dua, Broker of Record and co-founder of RE/MAX Quantum Realty Inc., Brokerage, Unit 101, 799 The Queensway, Toronto. I work with buyers and sellers across Toronto and the GTA and have helped more than 100 families sell. Four-plus years of active GTA transactions and over $100 million in sales volume. Every figure here comes from a published table, regulator or statute linked in the sources, so you can check all of it without asking me.
Reach me at [email protected] or 833-330-1925, or book a call.