Fun Winter Date Night Ideas in Toronto

The local vibe

When the temperature drops, Dundas West keeps it warm with culture, comfort food, and walkable streets. You’re close to beloved venues along Bloor, Roncesvalles, and Sterling Road, plus trails and rinks that glow under winter lights. Whether you’re planning a first date or a standing tradition, here are easy, grown-up ideas that pair perfectly with a night in after.

Evergreen highlights near Dundas West

Skate + stroll under the Gardiner The Bentway Skate Trail curls beneath the Gardiner at Fort York—a dramatic urban backdrop and a perennial winter favourite. It’s easy to reach from Dundas West by TTC or bike (weather permitting). Check their site for current programming and hours. The Bentway

Classic rink with the city skyline Nathan Phillips Square’s outdoor rink is a quintessential Toronto date—especially when the lights are on and the big holiday tree is up. The City lists features and on-site rentals; seasonal hours vary with weather, so peek before you go. City of Toronto

Art night, but make it easy MOCA Toronto (Sterling Rd., right by Dundas West) offers rotating contemporary art exhibitions and periodic free-admission evenings like “Free First Friday Nights.” Floor 1 is always free—great for a low-key culture stop before or after dinner. Museum of Contemporary Art Toronto

Independent cinema charm Settle in at Revue Cinema (Roncesvalles), one of the city’s longest-running independent theatres with community-driven programming—think themed series and cult classics. Or head a bit east to Paradise Theatre on Bloor for restored Art Deco vibes and a mix of films and live events. Revue Cinema

Laugh it off Looking for something light? Comedy Bar’s Bloor location (near Ossington) runs nightly stand-up and improv, perfect for a spontaneous date. comedybar.ca

Walk the Railpath On crisp nights, the West Toronto Railpath is a quick out-and-back for fresh air and easy conversation—an urban linear park connecting Dundas West and Sterling Road. Surfaces are paved and plowed, but always dress for conditions. City of Toronto

Recurring calendar (winter-friendly)

• Outdoor city rinks: Most outdoor artificial rinks generally operate late November through March, weather permitting. Check the City’s status page for closures before you lace up. City of Toronto

• MOCA Free First Friday Nights: Free admission on the first Friday evening of the month (5–9 pm); Floor 1 is always free. Museum of Contemporary Art Toronto

• AGO First Wednesday Night Free: A short TTC hop away if you want to turn your date into an art crawl—the AGO offers free admission on the first Wednesday night of each month (6–9 pm). Art Gallery of Ontario

• Local film + comedy series: Revue Cinema and Comedy Bar run themed series and seasonal showcases throughout winter—check calendars for the latest. Revue Cinema

Getting here & parking

TTC

• 505 Dundas streetcar connects Dundas West Station and Broadview Station with stops throughout the corridor—handy for rink and dinner hops. TTC

• Subway + UP Express: Dundas West Station (Line 2) links to UP Express Bloor Station in about a five-minute walk—useful if you’re coming from Pearson or Union. upexpress.com

Parking Green P lots are dotted around the neighbourhood, including Carpark 204 (1117 Dundas St W) and Carpark 235 (2201 Dundas St W). Rates and capacity vary—always confirm signs on-site. parking.greenp.com

Responsible use notes

We’re all for memorable nights—just keep it adult and respectful. Be mindful of local laws, skip public consumption, and plan your transit or a ride home. Outdoor activities are weather-dependent; check status pages for rink conditions and dress for the cold.

Set your night up right. Order ahead and we’ll handle the rest—free 1-hour delivery, 9am–11pm. Then bundle up, hit a rink or a show, and enjoy your winter date your way.
We deliver across Toronto’s west-end core—including Dundas West, Trinity Bellwoods, Little Portugal, Junction Triangle, Roncesvalles, and Parkdale—with free 1-hour delivery from morning to late night (9am–11pm). Exact availability can vary by address.