Short answer: they can roll over cobblestone streets, but I wouldn’t call it a smooth ride. A wheeled urban trash bin is usually designed for pavements, alleys, and smooth depot floors, so cobblestones are where the weak points show up. Small hard plastic or metal casters tend to catch in the gaps between stones, rattle loudly, and transmit every bump up through the bin. If the bin is heavy, those little wheels can also dig in or wear out faster.
The bins that do better are usually fitted with larger wheels, softer rubber treads, or pneumatic tires. Those absorb vibration and roll over uneven joints with less effort. A well-built frame and good swivel casters help too, especially when someone has to steer around tight corners or lift the bin over a stubborn stone. Brakes are useful on slopes, and ergonomic handles make a big difference because the user is often pushing or pulling a heavy load.
Surface condition matters just as much as the bin itself. Dry, tightly laid cobblestones are manageable; wet, cracked, or loose stones are much harder. Loose grit and winter ice can also make small wheels skid. So if this is a daily route, I’d recommend testing the bin on the actual street before buying a fleet. In general, wheeled trash bins can work on cobblestones, but they roll best with larger, softer wheels, moderate loads, and regular maintenance. They will never feel as effortless as they do on concrete—but with the right wheel setup, they are definitely usable.