Is that 1,000 m in a single session? Per week? I'll be keeping an eye on your ideas and stealing them. :)
Yes, it is - to get there in one session! I reckon it will take 2 months, and possibly a quick drive in the car to move hills. I think it will be on all of the roads that go up the escarpment by me. Bell School, 2 on Appleby, Steeles. My neon vest is going to get some use!
Cool idea! If you're interested, join me for a Grange Rd. session some time. It is closed for winter now except for some driveways near the top and bottom. We would need spikes or possibly snowshoes as the season goes on but the road would be nearly (or completely) deserted. And the Inglewood General Store is nearby with many delicious treats. :)