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The Best (or Worst!) Hills for Cyclists in Toronto

Posted by Derek Flack / July 20, 2009

Pottery Road Hill TorontoToronto may be a relatively flat city, but that doesn't mean that there isn't quite the collection of tough hills for cyclists to climb. As an avid rider I often masochistically ascend these roads to test my fitness and prove myself a man (full spandex and all!). But, truth be told, going down them is almost always more fun. And, as a commuter on a single speed, I avoid them like the plague.

So in a gesture to the arrival of the Tour de France to the Alps, I've compiled a list of some of the ones I alternately love and fear. I'd be happy to add more to the map at the bottom if readers can think of some that I've missed!

Bayview Extension (north end)
Coming in at around a kilometer, this is long by Toronto standards. Although not overly steep, I like the view of Don Valley from near the top. Seeing the parkland below always makes me feel that I've accomplished something.

Brimley Road Hill TorontoBrimley Road
Featuring bailout ramps for trucks that might lose control on its steeps, this is the toughest climb in the city. Longer than the rest, and plenty steep for Toronto, even hardcore cyclists will break a sweat on this one. Thankfully for commuters, Brimley isn't on the way to anything but Lake Ontario. But for those like me who like to ride down to the beach at Bluffer's Park, it's sure to be a suffer-fest on the way out/up!

Glendon Campus Lower Parking Lot
To climb this hill you need to break the rules and go up it the wrong way (it's a one-way heading east). But some might find the tree-lined road worth it for the switchback at the top. The sign there claims it's an 18% gradient.

Hogg's Hollow
Commuters in the north end know all too well that at Yonge and Wilson/York Mills all roads point up. For my money, I think the east side is the toughest to go up, and the most fun to go down.

Humber Valley near Old Mill
There's a number of ways to climb and descend in and around Humbercrest Blvd., all of which are exciting on the way down and challenging on the way up.

Lawrence Avenue East Hill TorontoLawrence Avenue East
When heading on Lawrence to the city's east end, I've often avoided the Bridal Path by riding down through Glendon's campus to where Lawrence resumes. It's definitely a short cut distance-wise, but damn this thing is steep. Straight and steep.

Poplar Plains
A great alternative to taking Bathurst north from Dupont, the bike lane makes this considerably safer, if a little steeper. The curves near the top of this hill have often allowed me to dream I was on a real mountain. Avid cyclists will enjoy going up Poplar Plains and down Russell Hill Rd. for interval training (and cornering work on the descent!).

Pottery Road
Currently undergoing some construction work, traffic on this hill can be a bit scary, especially when you're crossed-eyed from climbing. But, it's probably the fastest way to head out of this area of the Don Valley and into the city.

Redway Road Hill TorontoRedway Road
The steepest hill in the city, the service road down to the Sewage Treatment Plant has a gradient that tops 20%. This hill is as fun to descend as it is hard to climb! In a misguided display of bravery, I once hit 78kph on the way down. Happy to be alive, I won't do that again! Watch for mountain bikers using the road to pass between trails along the ravine wall and the corner at the bottom.

Sunnybrook Park/Hospital
This isn't a particularly steep climb, and the canopy of the trees keeps it nice and cool. When I cycle around Sunnybrook, I often take this route out of the park and onto the city streets. It's quite pretty and a great place for novice cyclists to get their climbing legs.

Rattlesnake Point
Although not in Toronto, whenever I'm looking to test my mettle (or kill myself!), I'll head out to Milton to climb this monster. Used for the Provincial Road Championships a few years back, this is as close as it gets to an alpine climb in the GTA. Sure, it's not as long, but with multiple switchbacks and a crazy gradient, this is an absolute leg-breaker!

View Hills for Cyclists in Toronto in a larger map

Lead photo is of Pottery Road, subsequent photos depict the hill described immediately below.



Torontonian / July 20, 2009 at 03:55 pm
Try the hill on Morningside Ave. from South Kingsway up to Windermere Ave.

You could also try the hill from Ellis Park Rd. up to Morningside Ave. and Runnymede Rd. and Ellis Park Rd. up to Bloor St.

I grew up in Swansea and am well familiar with them.
ryth / July 20, 2009 at 04:10 pm
Colborne Lodge Drive, coming out of High Park toward the queensway. It's short, but ouch.
Cyclist / July 20, 2009 at 04:15 pm
No love for the long, long steady incline of Rosedale Valley Road from Bayview to Park?
Carbonman / July 20, 2009 at 04:22 pm
Twyn Rivers in Scarborough. Toughest hill in the 416, bar none. Going west of course. Going east... hang on for your life and watch for cars coming at you over the single lane bailey bridge. Deadly.
Mark / July 20, 2009 at 04:25 pm
There are some decent hills within High Park itself. Swansea definitely has some great hills.
Carthy / July 20, 2009 at 04:28 pm
Great list. The Poplar Plains item reminded me of a time I was doing the loop mentioned - down Russell Hill, up Poplar Plains - as an interval workout and I kept passing a construction crew on PP that felt compelled to whistle and make a comment every time I rode by. We're talking 10 - 12 times. Felt like Groundhog Day with construction hats and Italian accents. It was very funny in an annoying kind of way.
1weasel / July 20, 2009 at 04:54 pm
Old Finch where it crosses the Rouge River is a good scenic spot.
chephy / July 20, 2009 at 05:27 pm
Heh, thanks for making a list of roads to avoid. For all the tough all-weather all-distance all-traffic-patterns rider image I present, I just hate hills. :-)

Alas, living uptown and commuting downtown means that I ride Poplar Plains a lot. Okay, sometimes it's Bathurst or Avenue or Yonge or Christie... but usually it's the loathsome PP, since it's best distance- and traffic-wise. I hate the way that sadistic hill gets steeper as you get closer to the top. That's so *nasty*.
Duarte / July 20, 2009 at 05:28 pm
The switchback by Belfountain/Brimstone nearly killed me.
DJ / July 20, 2009 at 05:56 pm
The Bluffer's Park hill that is mentioned is scary as hell. You are typically climbing a long hill with a narrow lane while some a-hole comes up behind you in a pickup towing a giant boat squeezing you off onto the gravel. Add to this a steady stream of cars traveling down the hill, finding no parking spaces, and heading back up.

However - highly recommend the recreation path a little further east that comes up the same cliff. It ends at a short road called Ravine Drive.
Wes / July 20, 2009 at 05:57 pm
I was also going to mention the climb up Ellis Rd / Ellis Park Rd from the Queensway up to Bloor. It's nice and steady from the Queensway up to Morningside, then you get a brief downhill before a shorter kick up to Bloor. I usually ride it as a loop by continuing up the hill Eastbound on Bloor, and then recover down West Rd and Colborne Lodge Rd back to the Queesway. It's a nice little loop! You can also switch it up a bit and on alternate laps do that steep climb in High Park on erm... I think Spring Rd?
katherine / July 20, 2009 at 05:58 pm
I recall Redway Rd as a child. My father was an avid cyclist and got me hooked on it as a child. We rode everywhere! I was about 9 years old when my father tried this hill on me. I ended up walking with my bike and dry heaving all the way to the top ... never again will I attempt this!

Another challenge I find is Main St going North to Danforth. Steep with lots of curves.
Ross / July 20, 2009 at 06:00 pm
The guys at HelloVelo have a nice downtown training loop that incorporates the Bayview extension and Redway road. It's great fun! http://www.hellovelo.ca/blog/?cat=13
Coren Kollector / July 20, 2009 at 06:50 pm
"Toronto may be a relatively flat city"

Tell that to those of us who aren't in great shape. Biking to the Lake is a delight, but biking back up north is almost entirely on an incline, and if you're tired, you feel every centimetre of it.
joe / July 20, 2009 at 06:52 pm
I second Twyn Rivers, it's a killer...maybe even literally, I wouldn't be surprised.
bill / July 20, 2009 at 07:26 pm
I would have to go for redway road that is a killer. I ride the bayview ext daily and you get used to it after awhile.
McD / July 20, 2009 at 07:26 pm
Should always mention Avenue Rd south of St Clair just because it heavily travelled. Once was doing down the hill stupidly drafting a porshe in his blind spot and got curbed when he turned right into his driveway at bottom of hill. Skin loss was not pretty. Driver was a really nice guy, took me to hospital, waited and then took me home. Said he would never forget, hearing a thump and looking to his right and seeing himself being passed by an upside down cyclist going 40 MPH.
Meghan (Making Love In The Kitchen / July 20, 2009 at 07:39 pm
I have to add in the ascent from the Sunnybrook/Don trail that comes out to Don Mills from behind the Science Centre. Woooh it's a toughy.
Dennisharvey / July 20, 2009 at 07:40 pm
What about Bayview extension South from pottery to moore? Traffic moves real fast here, but the wide shoulder south of the Governor's rd bridge makes it pretty reasonable. That sucker is looong, and gets steepest at the end. Might not be too too hard on a proper road bike, but gets me breathing pretty hard on my fixed gear, and I am on my bike 8 hours a day 5 days a week.
tom / July 20, 2009 at 07:56 pm
any of the little avenues between kingston rd. and queen in the beaches (lee ave. in particular) unfortunately a little too short but rather painful. probably similar to bluffers park
tom / July 20, 2009 at 07:57 pm
(this is an excellent post by the way)
John Semley / July 20, 2009 at 08:21 pm
Excellent post. Been looking on the net for something like this for a while.

Anyone have a nice utilitarian way to get from Christie and Bloor to Yonge and Davisville with the least oppressive gradient? I'm no bike pro or anything, just a guy with a secondhand bike who needs to get to his boss's house sometimes and hates showing up sweaty as piss.
Derek replying to a comment from John Semley / July 20, 2009 at 08:29 pm
I live near you, and my best bet would be to take Dupont to Avenue Rd., then a quick left and right onto MacPherson, which'll take you to Yonge. I'd then head up that way. There's really no way to avoid going up hill, but I find the Yonge St. one not so bad.
Don Watcher / July 20, 2009 at 09:14 pm
Once the Minto Skyyy condo is finished at the top of the hill, the city is going to reconstruct the Pottery Road hill, top to bottom. Should be safer for both pedestrians and cyclists.
john replying to a comment from Don Watcher / July 20, 2009 at 10:00 pm

Wait what does 'reconstruct' mean?

First time I went down that hill as a kid I thought I was going to die. I was on the road too, not the pussy trail to the side.

They should never change that hill. Its a right of passage for all 7 year olds.

Or perhaps it was, maybe there's more traffic there now than there was twenty years ago.
W. K. Lis / July 20, 2009 at 10:15 pm
Any road that has to climb the old shoreline of Lake Iroquois and crossing Davenport Road. That would be Lansdowne Avenue and Dufferin Street towards Avenue Road and Yonge Street.
Jonathan / July 20, 2009 at 10:40 pm
Oakwood from Davenport to St. Clair. It's not too long and not too steep... But watch out for the frequent TTC buses. There are stops at the top an bottom of the hill and the driver like to pull over and assume that no one is there.
Cliff / July 20, 2009 at 10:57 pm
The hills off Fallingbrook Rd. in the Beach are steep fun climbs as well. I remember watching the Toronto Police Service perform motorcycle rider training up the hills and they were experiencing some difficulty.
DennisHarvey replying to a comment from John Semley / July 20, 2009 at 11:20 pm
I agree with derek, but I might add in the little detour you can take along lawton, and brentdale to lascelles and through oriole park. Puts you right out onto Chaplin just a couple of blocks west of Yonge where it becomes Davisville. A little bit more distance than just going straight on Yonge, but you avoid the dip before Davisville, and get the pleasure of riding on calm side streets and through a beautiful park.
Derek / July 20, 2009 at 11:35 pm
Thanks for all the additions! That Twyn Rivers sounds awesome. I'll be sure to add it and some of the other ones to the map.

Three more that I remembered myself are Beechwood Drive, part of the loop that Ross shared above (quite hidden, but nice and steep) and Broadview from Queen to pretty much Danforth (not so steep but fun to hammer up), and Kingston Road from Woodbine to Victoria Park, another one that meanders its way for a while...

Let's keep'em coming! I'm getting some great ideas for loops, and a good list of places to avoid on my commuter bike!
Charles / July 21, 2009 at 01:06 am
Dufferin going back up north is painful. Especially the stretch around Davenport Rd. and then the stretch between Rogers Rd. and Eglinton Ave. West
W.N. / July 21, 2009 at 02:18 am
Greenwood, between Danforth and Gerrard, isn't as scenic as the ones above, and is shorter in length, but makes up for it in terms of sheer steepness. I've seen cars and buses in the winter unable to drive up the street when there's even a small bit of snow and ice on the ground. Two pluses: there's actually bike lanes on the street, and 8 times out of 10, there's a cop with a radar gun at the bottom to catch cars starting out at the speed limit of 40 kph, but easily reach 60-70 kph in a very short distance without touching the accelerator. Maybe the cop will check your speed and pull you over.
Phil B / July 21, 2009 at 08:04 am
Woodbine from the Lakeshore right to Danforth offers a very mild incline heading up to Eastwood, then it starts to get a little heavier toward Gerrard. After Gerrard you have a chance to race and hammer down hill to make the last effort upto Danforth.

Bathurst and Christie going upto St. Clair can be fairly heavy going, but in fairly short doses.

Dufferin going from Bloor up to Yorkdale has some pretty steep, but short inclines (leading upto St. Clair and just north of there).

Lansdowne north upto St. Clair from Davenport is a very very short but steep "wake-up" climb when I occasionally have to commute to North York.

Caledonia Rd. has some fairly steep parts and is rolling hills, so there is SOME reprieve, but is littered with stop signs and lights so not great for attacking, unless you want intervals.

Great list, I've not known about a bunch of these roads to visit... err... avoid ;-) Thanks!
Phil B / July 21, 2009 at 08:06 am
Dawes Rd. has a decent climb going both north and south between Secord Ave and Halsey Ave, if you catch the green light at Crescent Town it's made a bit easier, but you do have a nice lead-in coming down from either way.
Ryan L. replying to a comment from Phil B / July 21, 2009 at 08:20 am
There's some nasty patches in the road though. Not very big, but you wouldn't want to be caught by surprise by them after heading down the hill at top speed.
Ryan L. replying to a comment from tom / July 21, 2009 at 08:23 am
They're short, but at least after going downhill you're in a great spot for some flat biking on the trails along the water.
Ryan L. replying to a comment from tom / July 21, 2009 at 08:32 am
Triple Post!

An interesting note about some of the hills listed. Many of them were created during the last ice age when the shoreline was much higher than it is now (do a wiki for Glacial Lake Iroquois). If you go to google maps and click 'terrain', you can almost follow the old shoreline from the Bluffs, along the steep hills between Kingston road and Queen towards the steep drop off at Davenport downtown (Casa Loma would have been beach front property).

Rob / July 21, 2009 at 09:38 am
Anyone tried Beechwood Dr? There's the hill that leads from O'Connor down to the Police Dog training facility and into the Don Valley...it's a doozy...

jamesmallon / July 21, 2009 at 10:16 am
In Montreal the Bixi bikes tend to settle downhill through the day, and have to be taken uphill by Bixi trucks through the day. I can only imagine that the trend will be stronger here, with our more consistent descent to downtown in Toronto, if we ever get a Bixi.

McD, you forgot the rule: nobody in Toronto, cyclist or driver, is ever responsible for their own mistakes; everybody else is wrong.
john / July 21, 2009 at 10:32 am
Toronto is a flat biking city if you only go east-west.
Dacks / July 21, 2009 at 10:44 am
I've climbed most of these hills (gotta hit Twyn Rivers!) but Milkman's Road, which connects Craigleigh Gardens and the ravine down below, is always impossible for me. It's a combination of the terrain (gravel & deeply rutted earth), steepness and curve towards the top that I just can't deal with. Re: Humbercrest - I find the climb up St. Mark's Rd. to be the toughest.
Reality Check replying to a comment from John Semley / July 21, 2009 at 11:04 am
The easiest and safest way to get from Bloor to St.Clair/Davisville is to bike through Rosedale. Take Crescent from Yonge, over the Mt. Pleasant overpass, make a left on South (so that you're going East again as Crescent curves and turns into South... just look at a map), then left on Glen. Take Glen to the T intersection with Summerhill, left on Summerhill, then take the pedestrian bridge over the tracks at Maclennan. Follow Maclennan north, right on Inglewood with an immediate left on Welland. Take a left at Rosehill (for lowest climb) then right at Mt Pleasant till you get to Davisville.

It's a bit longer but the grades are easy, it's so much safer than Avenue or Yonge, and doesn't have the dip of Yonge between St. Clair and Davisville as Mt Pleasant uses bridges to take a level course over the cemetery. Poplar Plains is safe but oh god the hill. Another benefit of going through Rosedale and Moore Park is that you can stop into Summerhill Market and their great convenience store.
blah / July 21, 2009 at 11:41 am
Sorta OT but does anyone know of a beginner friendly cycling group looking for members?

Cycling is fun but I would rather enjoy it w/ others.

lister / July 21, 2009 at 12:26 pm
Two hills I tried in my fit youth: Twyn Rivers and Markham Rd south of Highway 7. Both monsters. We'd bike out to Twyn Rivers and ride down it at breakneck speed. Fortunuately none of us had any crashes. Lots of fun. Would never try that now. The Markham Rd hill was nasty after an unintended long bike ride up to Stouffville and we came back south along Markham Rd. Ouch. In either case I don't think we made it up 25% before giving up.

In adulthood: Poplar Plains and Mt. Pleasant. Poplar Plains was due to the illegal strike the TTC did several years ago. (Shake fist at TTC!) Didn't make it up, maybe got up a third of the way. Mt Pleasant was just a weekend bike ride. Didn't make that one either.

Getting from downtown or uptown to midtown is brutal unless you go way out of the way east or west.
Jennifwr / July 21, 2009 at 12:34 pm
I used to walk home from work down Glen Manor Drive in the Beaches between Kingston and Main, and have seen many hardcore cyclists try their best to climb that beast of a hill... One even started yelling for the last 50 or so meter push to the top last summer... only to be cheered on to complete it by myself and 3 people enjoying drinks on their lawn chairs. It was epic. I'd never try to bike up that hill in a million years.
mar. / July 21, 2009 at 01:42 pm
I live near St. Clair and Spadina. Going downtown via Russell Hill Road is a blast! Coming back up, I pretty much always go up around Casa Loma (Walmer/Austin Terrace). I (gasp!) take the sidewalk since rarely is there someone walking on it and try to 'sprint' up it to just get the pain over with. I find this route is better than Poplar Plains. Cycling on St. Clair is suicidal now.
Jennifer / July 21, 2009 at 01:52 pm
I live at St. Clair and Avenue, so I know the Russell Hill/Poplar Plains hills very well. I cycle every day, and I'm so happy that I am now able to make it up PP without stopping! A slightly easier way of getting up the escarpment to St. Clair is Spadina Road, past Casa Loma. The steep bit north of Davenport is short!
David / July 21, 2009 at 04:59 pm
Some years ago, I decided to try biking from Cabbagetown where I live to Consumers Rd where I worked. My first choice was via Leslie St and Sheppard Ave. Bad choice; it's pretty steep up Leslie to Sheppard and followed by another steep hill from Leslie to Don Mills. Still faster than the bus, though. I eventually settled for O'Connor to Victoria Park. While O'Connor up to Victoria Park isn't terribly steep, it is quite long. Lovely ride home though.
David / July 21, 2009 at 05:12 pm
I tried Milkmans Rd many years ago. There was no way to actually bike up; walking was the only way.

I also tried the Beltline from Moore Ave to Bayview Extension. I don't know what it's like now, but at the time it was very much like going through a dry stream bed. Another walking route and that was downhill.
Derek / July 21, 2009 at 05:13 pm
Just a little update: I did get a chance to add a bunch of the suggestions to the map, and will try to do a few more in the next little bit. Thanks for so many recommendations!

sgt. renfrew / July 21, 2009 at 05:16 pm
Lee? Glen Manor? Poplar Plains? Piece of cake compared to some of the others in the list if you how to change gears. I'm a fat lazy slob and I can ride 'em on a one speed... but the science centre hill , or the Sunnybrook driveway on the other side of the valley, almost have me walking.

A good one is the long climb up Don Mills from Lawrence to Sheppard (it's a good route north because it doesn't interchange with the 401). It's not super steep but it's long. On the way back down at 3AM when there aren't many cars, if you get the traffic lights right, you can fly all the way down (you can almost coast up the couple of little uphills near the bottom if you get up enough speed).

But if you really want hills, try Oak Ridges or Caledon (or the west coast).

John: it isn't so flat east-west if you go north of Bloor.
Mg / July 21, 2009 at 05:56 pm
Bathurst between Sheppard and Finch -- it cuts across the west branch of the Don, so that you hit a good downhill and an equally good uphill in either direction. Downhill you can hit 50-60 km/h without much difficulty, which helps to propel you part-way up the other side. But what's frustrating is the traffic light at the bottom. It's amazing how often it turns red in front of you, so that you lose the momentum and start up again from zero when it turns green.
piccola / July 21, 2009 at 08:47 pm
Mount Pleasant from Bloor to St. Clair. I run it fairly often and I can only imagine it's worse on a bike.
Wes replying to a comment from Cliff / July 21, 2009 at 10:50 pm
Just thought of another good one, but it looks like I was beat to the punch again. I love the steep climb on Fallingbrook Dr (note: not Fallingbrook Rd, right 'next door') in the East end near the Beaches.
Wes replying to a comment from blah / July 21, 2009 at 10:54 pm
re: Beginner friendly cycling group, the TBN immediately comes to mind: http://www.tbn.ca/
Simon Carr / July 21, 2009 at 10:58 pm
What, no Beachwood Drive?? It's closeish to Redway and Pottery Rd.

Inferno / July 22, 2009 at 02:13 am
going east from morningside and ellesmere..
even the busses struggle there
See / July 22, 2009 at 07:35 am
Hoggs Hollow! Go any direction from Yonge and Yorkmills and there is a hill to climb.
See / July 22, 2009 at 07:35 am
opps already on the list
joe / July 22, 2009 at 09:10 am
Awesome post. I've linked to it from the <a href="http://bikingtoronto.com/forum/topic.php?id=123";>BikingToronto Forum</a>.
Pat T / July 22, 2009 at 02:47 pm
Good call on Bluffers park road. Definitely the toughest hill in the city in terms of sheer gradient and length. The crapass abandoned condition of road tops it off. However I've found the traffic usually not too bad the 3-4 times I've done it.
Bill / July 23, 2009 at 11:40 pm
Too bad about the crap shape the road is in for the downhill on Bluffer's, and we cyclists could probably do without the speed bump at the bottom of the hill. It is definitely the best (worst?) climb in Toronto. I'm surprised that no one pointed out Don Mills north from York Mills up and over the 401??? I like climbing as much as the next cyclist, but I like a decent descent too. Weston Road north of the 16th Side Road over Strawberry Trail Hill, north of Vaughan, is a great hill from either north or south bound. The southbound climb is tougher and therefore gives great speed with little traffic and a good (safe) view when going north. It is worth making the ride just a little north of the city.
Jason / July 24, 2009 at 03:39 pm
Barrie Rd near the Humber River is the one I hate the most mainly because it's always on my return trip from downtown after I'm already tired. 30-40 degree slope for 300-400m. Tons of fun going down though.
RJ / August 10, 2009 at 04:47 pm
MILTON has the most incredible hills, listed below..

6th Line north of of 5th sideroad.
14 side road going up the escarpment
Bell Line School north of Derry rd.
Steeles Rd going up west of Tremaine.
Appleby Line north of Derry.
Applyby Line south of 5th sideroad.

Please exercise complete caution...
Hza / August 16, 2009 at 08:36 pm
I would add the stretch of Caledonia between St Clair and Eg. up down up down. Nuts.
janet / October 22, 2009 at 06:55 pm
I found a new killer hill.. it is a road (?name) that leads to the bike path in the Don Valley that goes from ET Seton Park and leads to Thorncliffe Park Drive. It is short, but the climb quite steep.
Paul / September 7, 2010 at 12:32 pm
This is an old thread, but there is another killer hill a couple of kilometers east of Brimley Rd. South that has yet been posted here. Meadowcliffe Dr. is about the same steepness as Twyn Rivers Rd. and I would contend that it is slightly longer (in the range of 100-150m longer).

See: http://maps.google.com/maps?f=q&;source=s_q&hl=en&geocode=&q=Meadowcliffe+Drive,+Toronto,+Ontario,+Canada&sll=43.709813,-79.245079&sspn=0.013075,0.016544&ie=UTF8&hq=&hnear=Meadowcliffe+Dr,+Toronto,+Toronto+Division,+Ontario,+Canada&t=h&z=16
Sterling replying to a comment from john / April 7, 2011 at 07:56 pm
"Toronto is a flat biking city if you only go east-west." - John

Not if you live uptown.

Finch East (though due to traffic, I'd suggest taking Cummer/McNicoll or Van Horne/Huntingwood) has at least a few decent hills.

One being in between Bayview and Leslie in both directions (especially westbound) where the two hills meet down at the Don River. In this case I highly recommend you stay on Finch and just use the sidewalk as it gets very little pedestrian usage. If you do choose to take Cummer, beware that it's a lot steeper and longer.

Another is just a little further east and seemingly just as you finish one hill, you get hit with another starting from Trudy (a street just after Leslie) up to Don Mills.

My advice for this one is to hang a right on Trudy and follow it to Seneca Hill Dr and head up to Don Mills from there. For some reason it's a lot more forgiving. Van Horne is another option but it's probably worst than taking finch. Fun as hell to ride down, though, of course.

Also there's the York Mills hill from Don Mills eastbound.

We all could go on, I'm sure.
Trek Bike Guy / August 26, 2011 at 02:05 pm
Old Kingston road up Military road or the opposite direction toward a church.
The first time I saw Military road, I thought it was a wall. But after doing Brimley rd a few times
and training up the Bayview extension, I think it's doable now.
I haven't tried Yonge and York mill but I did do Yonge and Wilson.
I recall my heart beating so fast that I wondered if I would keel over or
a bus might hit me and put me out of my misery.
Steven / February 2, 2012 at 11:48 pm
There are lots of steep hills in the Parkwoods/Donalda neighbourhood. Beveridge Dr., Brookbanks Dr., Roanoake Rd., Cassandra Blvd., etc.
Steven / February 2, 2012 at 11:53 pm
Moccasin Trail in Don Mills is also quite steep.
_n / March 16, 2012 at 02:17 pm
Yes! Great post! I was just thinking I need to get better at hills. Especially sustained hills. This is a good primer of what's around.
Jack / June 6, 2012 at 02:08 pm
Also in Sunnybrook park, there's a steep climb once you pass the riding stables going up to the soccer fields. That one's about half an hour into my usual ride and no matter how many times I do it, I'm always winded by the top of the hill. Coming back down you have to watch out because there are two sets of speed bumps on the road at the bottom of the hill and cars coming out of the Sunnybrook park restaurant parking lot. Another one at the end of Taylor Creek park that leads out to Victoria Park. Tough short hill. Watch out coming back down because there's a hard 90 degree right turn at the bottom. If you don't hit it, you're going into the creek.
Joe Posts / July 4, 2012 at 03:44 pm
We need an Easy Hills For Cyclists post. :-P

To get up The Hill from Dundas/Bathurst to St. Clair West/Bathurst where I reside, if I want an easier time, I blast up St. George to Dupont, slide over to Davenport, ride past Christie and go up Turner Road to the west of Hillcrest Park. Seems to be the shortest, quickest way up the cliff plus you can get good speed leading up to it on Davenport.
Xander replying to a comment from Torontonian / July 6, 2012 at 08:37 am
ellis and ellis park hills suck.. especially after a leisurely ride down them to the lakeshore...
Vziunas replying to a comment from Wes / June 25, 2014 at 09:31 am
That was the same route I took in the 80s and 90s...
RM / July 5, 2014 at 09:11 pm
Scarlett Rd. a couple of blocks south of Eglinton, up to St. Clair (my god, it's inhuman - bliss to fly down, hell to go up) It parallels Jane St. around the same area, which also can be a bit of a climb (so if you're using the Humber Valley Bicycle Path, take Royal York Rd (which has a bike lane from Eglinton to Bloor) and avoid the consequences (worse, the potholes on Scarlett make the uphill climb even more challenging) Most of the off ramps on the Humber Valley Path in Etobicoke North will give you a challenge to get to the main roads. Great post!
linda / July 5, 2014 at 09:52 pm
While I avoid hills like the plague I also live in Swansea...quite a collection we have here :-)
NS / July 6, 2014 at 09:16 am
redway road is challenging? man, just put it in low gear and sit and spin! I've climbed this hill from bottom to top on a 7" travel mountain bike and usually at the end of my don valley sessions to get back to loblaws. The hill behind the science center as well! Grow some legs and do more cardio ya lycra wearing weight weenies!
soo / July 20, 2014 at 09:22 am
For west-enders, here is my Hilly Loop. My goal today is 6 reps. Wish me luck!
B. Ross Ashley / September 14, 2014 at 11:35 pm
Did anybody mention Fallingbrook Road in the Beach?
Laurin replying to a comment from Carbonman / September 27, 2014 at 08:36 pm
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peter / August 5, 2015 at 10:28 am
No one (including the OP Derek Flack) has commented on the safety aspects (or extreme lack thereof) of these various hills. I would rate Bayview Extension Toronto's #1 DeathTrap.

A few years ago I was using it to train for a ride in the French Alps (the proverbial molehill vs. mountain by the way in case that is lost on anyone) and the condition of the road surface (terrible) and the traffic levels and haste (intense) made descending absolutely terrifying. Safely navigating those gaping cracks and crevices at 60+kph side by side very impatient drivers took it's toll on my nerves. I finally said "Life is WAY too short" and took to descending (slowly and respectful of uphill cyclists) on the opposite side, going against traffic (so I could at least see the motorized devils I had to deal with).

Does any other hill compare as a Life Threat?
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