Distance:  24 miles out and back
Elevation gain:  3323 ft 

This ride is expertly covered in Jim Moore’s 75 Classic Rides Oregon (see the “Oregon” section in Rides by Region).

This is a not-hard, not-easy climb and Best-of-the-Best descent through canopied woods and along open hillsides with grand vistas, all on an old highway that sees almost no traffic.  This is extreme Southern Oregon, so you won’t get the ferns and mossy maples of the Oregon rain forest, but the forest is still very pretty.  I love this ride, in both directions.  A perfect life would start every morning with it.   And you’re riding a stretch of old Hwy 99, which when I was a boy was the only route north through the Northern California valley and into Oregon, so there’s an added element of nostalgia if you’re a native of a certain age.

(To see an interactive version of the map/elevation profile, click on the ride name, upper left, wait for the new map to load, then click on the “full screen” icon, upper right.)

https://ridewithgps.com/routes/37959548

Start at the intersection of Hwy 66 and Old Siskiyou Hwy and ride Old Siskiyou until it turns into a Hwy 5 on-ramp. There’s a large dirt turn-out for parking at the intersection.  There is a mile or so of fairly level at the beginning, but if you want to warm up first, Hwy 66 is pretty and mellow in either direction. 

The first 7 miles of Old Siskiyou—to the Hwy 5 underpass—is steady climbing through lovely forest.  The pitch is just under hard—one more degree and you’d have to work, but as it is you just feel like you’re climbing strong today.  The canopy is cathedral, the road serpentines constantly and gracefully, the traffic is nearly non-existent because all the cars are on Old Siskiyou’s replacement, Hwy 5, and the road surface is next to perfect.  There’s even a 270-degree turn where you get to cross your route on an overpass—shades of Disneyland’s Autopia.

The first half of Old Siskiyou Highway: in the canopy

The second half of the ride is easier, more open, and big on vistas.  Leaving the Hwy 5 underpass behind, you climb up a short, straight, boring slog, and then the climbing is over.  You’re out of the trees and you’re alone on an wild, rocky sidehill far above the wide ribbon of Hwy 5 visible below you. At the fairly obvious summit you can see far into California to the south.  The best view of Hwy 5 is about 100 yards after you start down the other side—watch for it because it doesn’t last long.

From the summit to the end of the road is 4 miles of stready 25-30-mph, fairly straight downhill.  Given the fact that no car is ever going to be on this road (in the summer), the road surface  is in remarkably good shape, varying from excellent to good to patches of OK.   Turn around before the road sweeps you onto Hwy 5 and ride the 4 miles uphill back to the summit.  This last 8-mile out-and-back is only moderately rewarding, and if you want to ride to the summit (or the good view of Hwy 5) and turn around I won’t think less of you.

As good as the first 7 miles were going up, they’re even better coming down.   The curves are just big enough so that you don’t have to do much slowing and just small enough so that you can ride them hard and feel like a pro, and the pitch is just steep enough that you can get up speed without working and just shallow enough that you don’t have to do a lot of braking.  It’s a Best of the Best descent, a constant 20-30-mph ripper through dappled sunlight.

Shortening the route: Ride to the Hwy 5 underpass and turn around.

Second half of the ride: looking south at California and Hwy 5

Adding miles: The beginning of this route is on the route of the Dead Indian loop ride.

Just beyond the Hwy 5 underpass midway on our route is the turn-off for Mount Ashland Road, a challenging climb to the summit of the area’s tallest peak.

There is a bike path, the Bear Creek Trail, that runs up the valley from Ashland to Medford,  which is sometimes nicely in the thick of the reparian woods and sometimes boringly on the very shoulder of Hwy 5 (Note: the fire that destroyed Talent in Sept. 2020 laid waste to much of the countryside along the bike path).