Despite both being major North American cities, there is no continuous road connection between Atlanta, Georgia, and Toronto, Ontario. The obstacle? The Great Lakes.
Lake Erie, Lake Huron, and Lake Ontario form a massive aquatic barrier between the U.S. Midwest/Northeast and southern Ontario. While bridges and tunnels cross some waterways (e.g., Detroit–Windsor Tunnel, Ambassador Bridge, Peace Bridge at Niagara Falls), no road network traverses the lakes themselves.
The straight-line distance is ~950 km (590 mi), but the shortest driving route is ~1,200 km (750 mi) via Detroit–Windsor crossing.