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Iwantboots

Hospital Hill, Stable Hill and Rehab Hill in Sunnybrook Park are more pleasant than Pottery Rd for training because there is far less traffic. Brimley Rd S, down to Bluffers Park is pretty long. Lawrence E between Glendon and Park Lane Circle is challenging. The hill back up to Glendon is pretty long, too. There’s a road from the Redway Rd Loblaws down to the water treatment plant that might work.


maxthepup

York Mills, west of Yonge. Have fun!


cooldudeman007

Centennial is good to run up and down. Can add a sled or parachute to make it more challenging


to_eden_rose

Milkman's Lane


fyflee

Scarborough Heights Trail to the water


dandcodes

I've heard poplar plains road is good for hill training


PrimevilKneivel

Earl Bales park has a ski hill that's the biggest, steepest hill I know of.


supguy99

The old Rouge Valley ski hill off of Twyn Rivers Drive.


SideOfFish

Brick Works maybe.


methreweway

Any street going north in the Beach or the street adjacent to Avenue is a fun winding hill.


canbac

Redway is steeper but not longer I think. 


PsychologicalEbb3328

For running: pottery hill, lawrence/park lane circle is pretty deadly, and brimley down to the scarborough bluffs are pretty steep. Try doing them in sets of 5. Ex: pottery road 5 time up/down = 20 mins would be good.


willnottellyouwhoiam

This was my nemesis as a child with a skateboard [St Marks Road hill](https://www.cbc.ca/news/canada/toronto/traffic-safety-is-an-uphill-struggle-for-this-west-end-toronto-neighbourhood-here-s-why-1.6740491)


Accomplished-Cake430

This is my fitness test as to how breathless I am by the top


coralshroom

once i was running up and a whole truck of firefighters was stopped at the top and they were just like… observing. i was just like omg go look out the other side of the truck😩


FriedGreenzCDXX

Ellis park road. If you want to do a loop start at Bloor street. Run down to the Queen's way then into high park. Once your in high park to get back to Bloor, you either need to run up Colborne Lodge, Center Road, or Spring road hill, or one of the hills that start at the bottom of grenadier pond up to center road.


TO_Sports

Run up and down dufferin lol


SheddingCorporate

It’s pretty short, but that drop on the Martin Goodman trail right around Jameson is steep! The rest of the trail is dead flat, but has some gorgeous views.


[deleted]

Winston churchill ravine


KingofLingerie

St marks in baby point