Markham packs two very different moods into one city. Up in Unionville, a restored nineteenth century main street runs past a pond and park, with a municipal gallery and a bandstand along the way. Down at Kennedy and Steeles, the food stalls and tiny shops of an Asian mall keep things busy, and in between sit a civic theatre, a living-history museum and the Markham end of Canada's first national urban park. Whether you are after date ideas in Markham and Richmond Hill or just a good night out close to home, this side of York Region rewards a little planning. Here are Markham date ideas for 2026, mixing daytime date spots with date night plans from late fall through the first weeks of winter.
Main Street Unionville, Block by Block
Main Street Unionville: The old village street is lined with heritage storefronts, restaurants and a bandstand, and the Unionville BIA publishes a historic walking tour if you want the stories behind the buildings. Walk it in late afternoon, when the shop windows light up, and pick dinner as you go.
Varley Art Gallery of Markham: The City's public gallery sits at 216 Main Street Unionville, named for Group of Seven painter Frederick Varley. Two exhibitions, I Think This Means I Can Fly and Framing Identity, run until December 20, 2026. It opens Tuesday to Friday from noon to 4 p.m. and on weekends from 10 a.m. to 5 p.m., and it is closed on Mondays.
Toogood Pond Park: Steps from the shops, this 33-hectare park wraps around a pond with lookout points and a loop path. You may spot herons, ducks and swans, and the walk all the way around makes a calm way to finish a gallery visit.
Heritage Buildings on Markham Road
Markham Museum: At 9350 Markham Road, the museum spreads galleries and a collection of historic buildings across 25 acres of parkland. Fall hours are Wednesday to Friday from noon to 5 p.m. and weekends from 10 a.m. to 5 p.m., and once there is snow the grounds are listed for snowshoeing.
Markham Village: A short drive from the museum, the historic main street of the original Markham village has its own mix of older brick buildings, cafés and restaurants. It is quieter than Unionville and good for a no-fuss dinner after the museum.
December on Town Centre Boulevard and Main Street
Olde Tyme Christmas Candlelight Parade: Unionville's holiday parade comes down Main Street on Saturday, December 12, 2026, from 6:30 to 7:30 p.m. Arrive early for a spot along the curb, and plan dinner on the street afterwards, when the crowd thins out.
Flato Markham Theatre: The City's 527-seat theatre at 171 Town Centre Boulevard fills December with holiday concerts in its 2026/27 season, including Susan Aglukark on December 4 and A John McDermott Family Christmas on December 19. Parking is free, and the room is small enough that every seat feels close.
Markham Civic Centre outdoor rink: Next door at 101 Town Centre Boulevard, the City's outdoor rink is due back in December 2026, with exact dates still to come. Reach it by walking around the northeast entrance of the Civic Centre rather than through the building, and pair a skate with a show at the theatre.
Food Stalls and Shops at Kennedy and Steeles
Pacific Mall: At 4300 Steeles Avenue East, on the Markham side of the city line, this indoor mall is a maze of small shops and food stalls with signs in English and Chinese. Go hungry, split several snacks rather than one meal, and allow time to get pleasantly lost.
CF Markville: If the weather turns, Markham's big indoor shopping centre is open into the evening on weekdays and makes an easy backup for a walk and a coffee.
Open Sky in the Rouge
Tallgrass Trek, Rouge National Urban Park: From the Bob Hunter Memorial Park lot at 7277 14th Avenue in Markham, this easy 3.2 km loop crosses restored wetlands, meadow and grassland to wide south-facing views. With no tree cover it is all open sky, which is lovely at golden hour and bracing on a windy day. Part of the neighbouring Reesor Way trail is closed, so follow the posted routes.
Sample Date Itineraries
1. The Unionville afternoon: The Varley Art Gallery → a loop of Toogood Pond Park → dinner on Main Street Unionville.
2. The December evening: Skating at the Markham Civic Centre rink → a holiday concert at the Flato Markham Theatre → dessert on the way home.
3. The open-air morning: Tallgrass Trek in the Rouge → a late lunch of shared snacks at Pacific Mall.
Pro Tips for Memorable Dates
The Varley is closed on Mondays and the Markham Museum on Mondays and Tuesdays, so save the Unionville and museum dates for later in the week.
Parade night draws a crowd to Main Street Unionville, so leave the car a few blocks away and walk in.
Parking at Bob Hunter Memorial Park is free but limited, so arrive early on weekends, and the washrooms there are seasonal.
Rouge National Urban Park also stretches into Toronto and Pickering. Use the 14th Avenue address so you end up at the Markham trailhead.
Markham works best when you let it be two places at once: the slow, leafy pace of Unionville on one afternoon, and the noise and flavour of Steeles Avenue on the next. Between a new theatre season, a holiday parade and a rink coming back in December, there is plenty to fill the cold months.
Last reviewed: October 2026
Photo credits: Main Street Unionville by Nath87, CC BY 4.0, via Wikimedia Commons; Varley Art Gallery of Markham by Canmenwalker, CC BY 4.0, via Wikimedia Commons; Toogood Pond Park, Unionville by Nath87, CC BY 4.0, via Wikimedia Commons.