A collection of classic Portland cycling routes organized by different areas of the city and mileage. They all start and end close to the city, offering a solid feel to Portland areas ridden by many local road riders. Ideal for a quick spin, winter base miles or summer fun.
To note for people from out of town – Most of the rides here do have some elevation change
For larger fuller day rides, please check out the more detailed Routes.
Rides are organized by milage.
25 miles – South West Uppers – close in ride
29 miles – Pleasure no treasure – close in ride
35 miles – Rock Creek Classic
35 miles – Forest Park Shred (gravel bike or mtb)
38 Miles – Lake O Loop
40-90 miles – Boring and Back
50 miles – Vista house & Crown Point
51 miles – King Kong Classic
55 miles – Canby ferry
60 miles – Tickle Creek
68 miles- Bull Run
84 miles – Larch Mountain
South West Uppers
25m – Punchy – 2500ft : Loops
This is my “go to” less than 2hr ride. Sweet local roads with a high amount of climbing. Great if you are trying to mix interval training in. This ride captures a variety of great architecture along with a great scenic view of Portland from Council Crest. This ride can easily be modified by removing some loops.
Pleasure no treasure
29m – Punchy – 3200ft : West Loops
An older version of South West Uppers.Pleasure no treasure climbs Pittock Mansion first. Pleasure No Treasure – This is one of my favourite short punchy rides on sweet local roads. With a high amount of climbing, good if you are trying to mix interval training in. This ride also captures two classic view areas Pittock Mansion and Council Crest. This ride can easily be modified by removing some loops.
Rock Creek Classic
35m – Rolly – 3000ft : North West Lollipop
Rock Creek is a staple for roadies wanting a shorter workout with fewer cars and a nice mix of hills and rollers. Ride it as hard as you like, the pleasure is up to you to define on this one.
Forest Park Shred
35m – Dirt Shred : North West Loops
Most of my routes in the classics are road, but Dirt? No problems, check out this close in ride to get your fix. It’s mainly firelanes, but super fun on a CX bike or maybe hardtail mtb. With some fast downhill rippers and some testing punchy nutty techy climbs.
Lake Oswego Loop
38m – Rolling – South Loop: 2200ft
Lake O Loop is a great ride, short and sweet. Passes through of a mix of unique suburbs including Lake Oswego and Oregon City for a change of scenery.
Boring (Oregon) and back
40-90m – East- Flat – Out & Back East
You want a simple flat car free ride. This smooth top multi-use trail (no motor vehicles) goes out for over 20miles to Boring, Oregon. You can stop and turn around at any point. At the end of the trail in Boring, there is water, restrooms and a store. This is great in colder winter months as you don’t have to deal with sweat and cooling sweat! from drastic climbs.
Vista House / Crown Point
50m – Moderate Hilly – 1,800ft : East Out and Back
Riding into the Columbia gorge is always breathtaking, the old historic highway 30 is popular in the summer with cyclists. The ride offers amazing views from the Women’s Forum and Vista House along with gradual climbs and multiple route variations. One thing to watch out for in high season, the locals of Corbett (which you pass through) can be pretty aggressive with their driving and the roads narrow in points.
King Kong Classic
51miles – Punchy – 4500ft
This is a classic Portland winter training ride , originated by Ira Ryan of now Breadwinner Cycles. It’s perfect in any season and has some punchy climbs and some nice sceanic backroads.
Canby Ferry Loop
54m – Rolly – 3,100ft : South Loop
60m – Rolly – 2,500ft : East Loop
Tickle Creek is one of those more meandering rides, good in any season, not too far from stops and explores some lesser travelled roads. Some further Tickle Creek info and pictures can be found here
Bull Run Especial
68m – Hilly -3,200ft : East Loop
Bull Run to the East of Portland covers amazing idyllic road climbs and drops to rivers. This ride has a good amount of elevation gain so beware, but this ride has to be experienced to be believed, a true classic to the area.
Further Bull Run details here :
Larch Up Mountain
84m – Sustained Hilly – 4,300ft : East Out and back
Larch Mountain is an extension from the ride above. The actual Larch mountain climb is brilliant, deep in woods, winding and a challenging climb. but be aware it’s 14miles of climbing and 3000ft just in that one climb. But the views from the top are amazing and the descent is a piece of cake. Take a jacket in earlier months as it can be cold coming down.
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