55Doable with Planning
New York City
United States
Americas
NYC is challenging — street level is fine, but the subway will break you.
Best stroller: Compact
Canada
Toronto
71/100Stroller-Friendly📊 Medium confidence
Toronto is flat, multicultural, and family-friendly — cold winters are the biggest challenge.
✅
Bring your stroller
This city is stroller-friendly. Compact strollers work best.
Key Factors
- •Generally manageable
- •Compact stroller recommended
Watch Out For
⚠️Some older TTC stations
📋 The Bottom Line
Toronto is a great city for stroller families. It's largely flat, the TTC subway has been improving accessibility (though some older stations still lack elevators), and Canadian culture is warmly welcoming to families. The PATH underground network is a game-changer in winter — you can stroll for kilometers indoors. Summer brings fantastic waterfront activities and festivals. The diverse neighborhoods mean family-friendly restaurants of every cuisine.
Quick Facts
Overall Score71/100
Best StrollerCompact
Biggest ChallengeSome older TTC stations
Data Quality📊 Medium confidence
Gear Recommendations
- 🎒Compact stroller works well on flat terrain
- 🎒Winter weather protection essential November–March
- 🎒Rain cover for spring and fall showers
- 🎒Lightweight fold for TTC and streetcars
Score Breakdown
Terrain20%
8/10Slopes20%
8/10Transit12%
7/10Elevators12%
7/10Facilities12%
7/10Crowding12%
6/10Friendliness12%
8/10Neighborhood Guide
🟢 Where It's Easy ✓
- •Harbourfront / Queens Quay - Flat waterfront, playgrounds, ferries
- •Toronto Islands - Car-free, flat, beaches, amusement park
- •High Park - Large park, zoo, playgrounds, flat main paths
- •Distillery District - Pedestrian-only, cobblestones but flat
- •PATH underground - 30km of indoor walkways, perfect in winter
🟡 Where You'll Struggle ⚠
- •Some older TTC stations - No elevators
- •Kensington Market - Narrow, crowded, bohemian chaos
- •Bloor Street winter sidewalks - Ice and slush
- •Casa Loma area - Hilly residential streets
- •Streetcars - Some older models have steps
🎒 When to Bring the Carrier 👶
- •St. Lawrence Market on Saturdays (very crowded)
- •Kensington Market (narrow, bohemian, tight)
- •Eaton Centre at holidays (mall crush)
Parent Wisdom
❌ What Parents Wish They'd Known
- ✕Winter sidewalk ice (Toronto ice is treacherous)
- ✕Not using the PATH system in winter (it's a lifesaver)
- ✕Assuming all TTC stations have elevators
- ✕Kensington Market with a wide stroller (too narrow)
- ✕CN Tower without pre-booking (long queues with no shade)
⭐ Parent-Recommended Spots
- ★Toronto Islands - Ferry ride, beaches, flat, Centreville amusement park
- ★Royal Ontario Museum - World-class, accessible, family galleries
- ★Ripley's Aquarium - Modern, accessible, mesmerizing
- ★High Park Zoo - Free, small, accessible, charming
- ★Ontario Science Centre - Interactive, family-focused, accessible
Similar Destinations
Other cities you might want to explore
38Challenging
San Francisco
United States
Americas
San Francisco's extreme hills make it one of the toughest US cities for strollers — flat areas exist but you have to find them.
Best stroller: Rugged
78Compact Stroller Paradise
Amsterdam
Netherlands
Europe
Amsterdam is stroller paradise — flat terrain and everyone yields to wheels.
Best stroller: Compact
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