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Ride to Callahan’s

  • Length:
    23.8 miles
  • Difficulty:
  • Nearby Cities:
  • Region:
    Southern Oregon
  • Attributes:
    Extended Climbs, Rural, Wildlife Views

Elevation Chart

Stay Safe

In Oregon, a bicycle is legally considered a vehicle, and the same Oregon road laws apply. Please “be seen” and practice safe riding. Vehicle traffic, farm equipment and narrow shoulders exist on many Oregon roads, and you may find that construction projects, traffic or other events may cause road conditions or signage to differ from the map results, ride descriptions and directions. For travel options plus weather and road conditions, visit, call 511 (in Oregon only), 800.977.6368 or 503.588.2941. Routes listed on this website are for informational purposes and intended as a reference guide only.

Start south on Ashland St 157 feet (48 meters)
Turn left onto OR-66 E/Ashland St
Continue to follow OR-66 E
5.3 miles (8530 meters)
Continue east on OR-273 N/Old Hwy 99 S/Old Siskiyou Hwy 13.2 miles (21168 meters)
Turn left onto OR-66 W/Green Springs Hwy
Continue to follow OR-66 W
5.3 miles (8530 meters)

The climb to Callahan’s is a beautiful ride from the valley floor to 4,000 feet. The climb itself isn’t terribly difficult, but it certainly isn’t easy either. The real climb begins half a mile past the right turn onto Old Highway 99, with an average gradient of just less than 6% for six miles. It twists and turns up the oak woodlands with occasional views of Soda Mountain, Pilot Peak and Emigrant Lake. The top can be a bit of a disappointment after a hard climb. The traditional turnaround point at Callahan’s restaurant is little more than a freeway entrance with no real view except the freeway and snow-moving equipment. If it is views you wish, continue on Old 99, climbing for a couple miles and 500 vertical feet to Siskiyou Pass. For the best views – and if another 2,800 feet of climbing sounds enchanting – follow signs to the Mount Ashland Ski Area. Enjoy the descent back to the valley; the winding curves slow downhill car traffic down but bicycles will fly right through them. I’ve had friendly motorists allow me to pass on several occasions. A plumbed spring has been available to supply water to thirsty cyclists near the summit in the past. This spring was contaminated by a chemical spill on I-5 in October 2004. The water is not safe and should be avoided. DO NOT DRINK FROM THIS SPRING.

About This Ride:
Regardless of your final destination, this is an out-and-back ride. Except for the freeway, Old 99 is the only access road to Callahan’s. From Ashland, follow Highway 66 (Green Springs Highway) for 7 miles south. Turn right on Old 99 and after reaching the destination of choice, return the way you came.

This ride typically will start at the Roasting Company in Ashland but is short enough to be added on rides beginning anywhere in the Bear Creek Valley.

Motorized Vehicle Traffic: Light to moderate; some blind curves on Old 99.

Seasons: All, although heavy winter snows impact the upper reaches

This ride brought to you by Siskiyou Velo.


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