It's looking like a ride using 401 to 427 to queensway to Don Valley Parkway to 401, repeat ~ 25 times is going to be within the 'in city' rules. Now to plot it, plan it and conditions permitting ..... ride it !
Greetings, Bill ...
My 2¢ worth.
Google Maps is useful for a general, high-level view of the outline of a city. But when zooming in to determine more precise boundaries, GM’s city outline fades away and eventually disappears; that's not helpful. Also, GM’s boundaries follow land areas, so a bridge over a waterway, for example, appears to be NOT in the city of interest.
For my In-City rides, I have used, and recommend,
ACME Mapper to determine EXACT boundaries for any city (or county, state, province). Sometimes, a boundary is down the middle of a street or freeway (southern I-295 in Jacksonville, FL, for example); ACME Mapper will show this correctly. Jagged boundary lines are also accurately shown with ACME Mapper (Sacramento, Tucson, Chicago, as examples). Non-city “islands” surrounded by a city are also clearly indicated (San Diego, Jacksonville).
From your route description, and using Google Maps, which uses speed limit data in calculations …
The CCW loop, start/end on ON-401 just west of Don Valley Pkwy (arbitrary start/end point)
--
https://goo.gl/maps/WYDPviCYmyhnseV29
-- ON-401 W, ON-427 S,
The Queensway E (and at its end, continue on Gardiner Expy E), Don Valley Pkwy N, ON-401 W
-- 39.8 miles (64 km), 56 minutes, avg speed 42.64 mph (68.57 kph)
-- your 25 laps would be 995 miles (1,600 km)
-- duration would be 23 hr 20 min (but that’s riding time only, with NO stops for fuel, food, breaks)
A slightly different interpretation would be the route as above, except from ON-427 S,
Gardiner Expy E all the way to Don Valley Pkwy. (Maybe that was your intent, anyway?) ...
--
https://goo.gl/maps/DbZnFE4BftEcW2DB9
-- 39.6 miles (63.7 km), 42 minutes, avg speed 56.57 mph (91 kph)
-- 25 laps would be 990 miles (1,592 km)
-- duration would be 17 hr 30 min (also without the stops for fuel, food, breaks)
That seems feasible -- may need another lap, though, for "insurance" mileage!
Regards ... Dave