Riders pass Keene Creek Reservoir on Highway 66 (Green Springs Highway) on the Cascade Siskiyou Scenic Bikeway /
Photo by Muuqi Maxwell

Here's a ride with big rewards for anyone ready to put in the hard work. The 55-mile Cascade Siskiyou Scenic Bikeway, which starts and ends in beautiful Ashland, includes 5,085 feet of steep and winding climbing through oak savannah and fir forests. It also features some of the fastest descending you'll ever hope to find.

Length: 54.8 miles
Difficulty: Challenging
Altitude Gain: 5,085 feet 
Start: Ashland
Attributes: Extended climbs, forest, mountain views
Interactive Map and Additional Ride Information: Visit Ride With GPS
Additional Area Resources: RideOregonRide.com

Click to see a printable map and turn-by-turn directions


Route Description

By Dan Shryock

Serious cyclists love this challenging 55-mile route that delivers switchbacks, scenery and speed. Yes, lots of speed.

There’s 5,085 feet of climbing as well. You can’t go fast downhill until you’ve paid your dues going up.

The Cascade Siskiyou Scenic Bikeway starts and ends at Garfield Park in Ashland, home of the famous Oregon Shakespeare Festival, great restaurants, wineries and breweries.

The official route leads east out of town for 2.5 miles before reaching your only course decision of the day. You can follow the official route and head uphill east on Highway 66. Or, you can turn north on Dead Indian Memorial Road and ride the loop clockwise. There’s plenty of climbing either way and anyone going clockwise completes most of the climbing in one long, 12-mile grind.

Highway 66 looking over Bear Creek Valley on the Cascade Siskiyou Scenic Bikeway /
Photo by Muuqi Maxwell

For this description, stay with the official route and follow Highway 66. The road starts to tilt up about 10 miles into your ride and quickly turns into a series of sun-baked switchbacks among the oak trees. To the right is a view down and across Bear Creek Valley and the Cascade-Siskiyou National Monument area. Pilot Rock, a prominent 25-million-year-old volcanic plug, is in sight as well.

After about 6 miles of climbing, the highway reaches the Green Springs Mountain Summit marked at 4,551 feet in elevation. You’ve just completed more than 2,600 feet of your total climb. Notice that this is where the popular Pacific Crest Trail leads hikers north and south.

Ahead is welcome shade among the Ponderosa Pines and Douglas Firs. A popular rest stop, Green Springs Inn (www.greenspringsinn.com) - at the intersection of Highway 66 and Hyatt Lake Road - is a great place to refill water bottles, catch your breath and get something to eat. Cyclists like to sit on the outdoor deck and enjoy the inn’s selection of pies.

If you want some very cold, fresh water, head for the pure mountain spring located 1.5 miles downhill at Tub Springs State Wayside. Don’t be surprised to find local residents filling large containers there. This water tastes great. Remember, however, there’s a climb back up to the restaurant.

Rested and refreshed, leave the Green Springs Inn and ride north on Hyatt Lake Road for another 3 miles before the route levels off and runs for another 11 miles through the trees. You’ll pass Hyatt Reservoir and Howard Prairie Lake with a 1.5-mile downhill streak between the two. If you’re looking for another food stop, the Howard Prairie Lake Resort is a half mile off the route. Watch for the signs.

Mt. McLoughlin

As you near the end of this stretch, look east and see Mt. McLoughlin. It’s not hard to find, standing nearly at 9,500 feet. This may be time for a photo opp.

At about the 35-mile mark, you’ll turn left on Dead Indian Memorial Road and ride a flat mile or so before the last grinding 3 miles uphill to your final summit. At the top, stop and rest. If your heart is racing from the physical effort, it’s sure to beat even faster with the exhilarating descent ahead.

The road heads down for 12 miles through a series of watershed canyons. Speeds can easily exceed 40 mph before tight switchbacks force you to scrub most of that speed for safety’s sake. Once at the bottom, turn right on Green Springs Highway (Highway 66) and head back into Ashland.

Lodging Ideas

Bike campers can make this a multi-day ride by staying at Hyatt Reservoir or Howard Prairie Lake Resort.

There are several great places to stay in Ashland including the Ashland Hills Hotel & Suites located less than a half mile from the designated route. For additional lodging ideas in Ashland, see our directory.

 Bike Friendly Businesses

Howard Prairie Lake Resort and Ashland Hills Hotel & Suites are two of eight Ashland-area businesses that participate in Oregon's official Bike Friendly Business program. See the list and search for bike friendly businesses throughout the state.