With the big parades behind us, the next few weeks belong to markets, lantern walks, skating and an early taste of the holidays. Here's my region-by-region look at what's on between November 27 and December 13, 2026. Events from my earlier roundups (Santa Claus parades, the Cavalcade of Lights, the One of a Kind Show and the Distillery Winter Village) are covered there. I checked dates and details against organizer and municipal websites at the time of writing, but plans can change, so please confirm with the official link before you head out.

Photo: Valentin on Unsplash

Toronto

• HarbourFrost at Harbourfront Centre (until Dec 20) — The waterfront's winter festival runs Friday evenings and weekend afternoons into the evening, with a holiday market, a small train ride, fire and circus performers, and live music on weekends. Admission is free, with a few ticketed extras. Hours and line-up: harbourfrontcentre.com.
• Evergreen Brick Works Winter Market (Sundays: Nov 29, Dec 6, Dec 13, 11 a.m.–5 p.m.) — Artisan and vintage vendors, a food court and fire pits in the Don Valley at 550 Bayview Ave. Details: evergreen.ca.
• Christmas at Casa Loma (select dates from Dec 4) — The castle is decked out for the season, with daytime visits and an evening Holiday Lights experience on select nights. Tickets are sold online; daytime and evening admission are priced separately. Dates and prices: casaloma.ca.
• Festive Nights at Black Creek Pioneer Village (Sat, Dec 12, 6–9 p.m.) — An evening visit to the lantern-lit heritage village, with music, storytelling and seasonal treats. Tickets required; another evening follows on Dec 19. Details: blackcreek.ca.
• Glow in the Wild at the Toronto Zoo (Thursdays to Sundays) — An after-dark walk of roughly 1.5 km past illuminated lantern displays. The season runs into early January, with entry from 5:30 p.m. and closures on Dec 24 and 25. Details: torontozoo.com.

Thinking of living in Toronto? See homes and rentals on my Toronto page.

York Region

• Richmond Hill Merry Marketplace (Saturdays: Nov 28, Dec 5, Dec 12, 4–8 p.m.) — An outdoor evening market at Richmond Green Park with local makers, food, a fire pit, weekly themed activities and visits with Santa. Details: richmondhill.ca.
• Aurora's Christmas Market (Nov 27–29 and Dec 4–6, 5–8:30 p.m.) — Two weekends of holiday vendors, workshops and nightly entertainment at Aurora Town Square, 50 Victoria St. Free to attend, with some ticketed shows. Details: aurora.ca/christmasmarket.
• Richmond Hill Group of Artists Show and Sale (Nov 28–29, 11 a.m.–5 p.m.) — A small local show of original paintings by member artists at the Mill Pond Gallery, 314 Mill St. Details: calendar.richmondhill.ca.
• Holiday cards and gift tags workshop, Richmond Hill (Sat, Nov 28, 10 a.m.–1 p.m.) — A City-run watercolour class at Rouge Woods Community Centre; no experience needed. Registration through the City's recreation portal. Details: calendar.richmondhill.ca.
• Holly Cole: Swinging Christmas (Sat, Dec 12, 8 p.m.) — A holiday jazz concert at Flato Markham Theatre, 171 Town Centre Blvd. Tickets from $78, with $20 youth tickets. Details: Flato Markham Theatre box office (City of Markham).
• Also worth watching: Vaughan's Christmas tree lighting at City Hall and Unionville's Olde Tyme Christmas are usually held in early to mid-December, but neither had 2026 details posted when we checked. Watch vaughan.ca and markham.ca.

Thinking of living in York Region? See homes and rentals on my York Region page.

Peel

• The Nutcracker at the Living Arts Centre, Mississauga (from Sat, Nov 28) — The holiday classic opens with a 2 p.m. show on November 28, with more performances listed. Details: mississauga.ca and livingartscentre.ca.
• Caledon Tree Lighting (Tue, Dec 1, 5:30–7:30 p.m.) — The Town's annual celebration outside Town Hall, 6311 Old Church Rd. Bring a non-perishable item for the local food bank. Details: caledon.ca.
• Bolton Santa Claus Parade and Christmas in the Valley (Sat, Dec 5) — The Bolton Kin parade steps off at 11 a.m. and travels north along Queen Street (Hwy 50). Downtown Bolton's holiday street festival runs 11 a.m.–7 p.m. with vendors, food trucks and kids' activities, wrapping up with a tree lighting at 7 p.m. Details: boltonkin.com and visitcaledon.ca.
• Brampton Steelheads school-day game (Wed, Dec 9, 11 a.m.) — A daytime OHL game against the Guelph Storm at the CAA Centre. Schedule and tickets: chl.ca/ohl-steelheads.
• Sunday Family Fun at Benares Historic House, Mississauga (Sundays: Nov 29, Dec 6, Dec 13) — Free drop-in crafts and games at the heritage house in Clarkson. Details: mississauga.ca.

Thinking of living in Peel? See homes and rentals on my Peel page.

Simcoe County

• First Light at Sainte-Marie among the Hurons, Midland (Thursdays to Sundays until Dec 13, 5:30–9 p.m.) — Thousands of candles light up the reconstructed 17th-century site, with live music and an artisan market. Admission is $15, and children 5 and under are free. Details: saintemarieamongthehurons.on.ca.
• Barrie Colts home games (Sat, Nov 28, 7:30 p.m. and Thu, Dec 3, 7 p.m.) — OHL hockey at Sadlon Arena, against Kingston and then Sault Ste. Marie. Tickets: chl.ca/ohl-colts.
• Orillia Christmas Market (Fri, Nov 27, 5–9 p.m.) — Downtown Orillia's evening market, with a children's candlelight parade at 6:30 p.m. and late-night shopping. Details: downtownorillia.ca.
• Holiday markets around the county: Several farms and resorts run weekend holiday markets through December, but not all had 2026 details on their own websites when we checked. Tourism Barrie and the Town of Innisfil's event calendars are good places to look.

Thinking of living in Simcoe County? See homes and rentals on my Simcoe page.

Durham

• Pickering Winter Wonderland (Saturdays: Dec 5 and Dec 12, 11:30 a.m.–3 p.m.) — Ice carving, buskers, s'mores, crafts and a holiday market at Millennium Square and the Nautical Village on the waterfront. Details: pickering.ca.
• A Storybook Christmas at Pickering Museum Village (Nov 28 to Dec 6, select dates) — A holiday story adventure for kids through the village's historic buildings. Registration required. Details: pickeringmuseumvillage.ca.
• Ajax holiday events — The "It's Almost Christmas" market runs Sunday, November 29, 2–7 p.m. at the Ajax Community Centre (free). A family magic show follows on Saturday, December 5, at 11 a.m. and 2 p.m. at the Ajax Centre for the Arts ($20). Details: ajax.ca.
• Oshawa Generals home games (Fri, Dec 4; Sun, Dec 6; Sun, Dec 13) — OHL hockey at the Tribute Communities Centre. Times and tickets: tributecommunitiescentre.com.
• Station Gallery, Whitby (until Dec 26) — Two current exhibitions at the community art gallery at 1450 Henry St. Details: stationgallery.ca.

Thinking of living in Durham? See homes and rentals on my Durham page.

Photo: Ross Sneddon on Unsplash

Find your place in the GTA

If one of these communities has caught your eye, take a look at the current listings on my rentals page, or call or text me at 416-357-4076. I'm happy to talk through neighbourhoods, commutes and what's available. Event details are provided for general information only. Please confirm with each organizer before you go.

Anthony Ochoa, Sales Representative, Red House Realty Inc.