Notes: The routes will be updated with details and possibly changed before the ride. Also, the elevation profiles below use different scales; make sure to check the scale when judging climbs and comparing days. It’ll make you feel better. 

Lodging Baggage/Shuttle Service: If you book lodging with one of our partner properties, we'll drop off and pick up your baggage, and provide scheduled passenger shuttle service. Use this list to book with our partners: OR 2025 Lodging List.

Day 0 – Saturday, June 21: Check-in, Ashland

Site: TBD

What a great place to gather for our wild week. Come a day early or roll in Saturday – either way you’ll be charmed by one of the most beautiful towns in the West. Check out sprawling Lithia Park, visit a winery, stroll through downtown – and then come over to camp to get ready for the two-wheeled fun to come.

Day 1 – Sunday, June 22: Buncom-Jacksonville Loop – 64 miles, 4,480 feet of gain

Site: TBD

Let’s head for the hills! After a smooth, flat start you’ll rise into the foothills of the Siskiyou Range, through Talent and into rolling pastureland and vineyards. After the early work, revel in the adrenalizing descent to the preserved ghost town of Buncom. Then wend your way through the Applegate Valley and up into Jacksonville, where 170 years of history are reflected in the storefronts of Main Street. After a break in a shady park (and some town exploration if you’d like), swoop down into the Rogue Valley and back to Ashland.

Day 2 – Monday, June 23: Valley Explorer – 35 miles, 1,650 feet

Site: TBD

You definitely woke up your legs yesterday, so for Day 2 let’s spin out the kinks with a relaxed riding day. Today we’ll explore nearly the entire length of the remarkable Bear Creek Greenway, which connects multiple towns from Ashland to Medford and traverses an impressive diversity of terrain and environments. Break off from the trail in Medford and take lower-traffic streets past two golf courses before you emerge back out into the countryside. Views of mountains to the west, east and south frame your backroad return to Ashland, where you’ll still have plenty of day left for being a tourist.

Day 3 – Tuesday, June 24: Ashland to Klamath Falls – 69 miles, 5,980 feet

Site: Moore Park

Take your time today. Immediately after leaving Ashland, you’ll turn onto Memorial Road, which is the biggest/longest climbing combo for the week. Focus on the visual transition from golden grasslands to alpine forest as you snake your way up 12 miles and 3,300 feet. Once you’re up top, the next five miles provide a high-prairie downhill break before you turn onto Keno Access Road – one of those remote, barely traveled forest roads we all love – for a relaxed 27 miles. Then drop down into Klamath Falls via Keno, ending at lush Moore Park on the edge of Klamath Lake.

Day 4 – Wednesday, June 25: Bonanza/Langell Valley – 67 miles, 1,860 feet​

Site: Moore Park

It’s another one-two like the first two days: You worked hard getting to Klamath Falls, so spend a day rolling through level, quiet pastures and around scattered buttes. Take in the rangeland of south central Oregon; this is a land of country stores and community granges, impossibly big ranches and small towns where everyone congregates on Saturday night. It’s a day to cruise along the country roads and have conversations with your fellow adventurers.

Day 5 – Thursday, June 26: Keno/Clover Creek – 55 miles, 2,800 feet (long option: 71 miles, 5,110 feet)

Site: Moore Park

We just can’t get enough of those isolated forest roads, so we’ll backtrack a bit to ride another one. Pedal through Keno, up Keno Access Road, and then hang a right to plunge down undulating Spencer Creek Road, where you’re unlikely to see a vehicle that isn’t part of our event. You’ll connect with Clover Creek Road, riding to Keno “the back way,” before returning to Moore Park.

Long option

Feel like a little climb? Take on an optional up-and-back on Hamaker Mountain. A barely used road takes you up, up, up for 8 miles – then of course it’s down, down, down. It’ll certainly add an extra element to your ride.

Day 6 – Friday, June 27: Klamath Falls to Ashland via Highway 66 – 65 miles, 3,800 feet

Site TBD

We got the harder of the two ways between Ashland and K Falls out of the way on Day 3. Today won’t be quite as grueling, and it features one of the most thrilling carnival rides in Oregon: the descent down Green Springs Road toward Ashland. After crossing the Klamath River a few more times, experience Oregon’s own Highway 66, where Pinehurst and Lincoln are the only “towns” on the route. Still grinning from the descent, you’ll pass gorgeous Emigrant Lake on the way back into Ashland.

Day 7 – Saturday, June 28: Old Siskiyou Highway/Mt. Ashland Out-and-Back – 46 miles, 5,430 feet

Site: TBD

Don’t freak out at the elevation gain (unless it’s a positive freakout) – this is an out-and-back that you get to cut to whatever length you like. After another pass by Emigrant Lake, a right turn puts you on the Old Siskiyou Highway, one of our favorite climbs in Oregon. It’s not long, it’s not difficult – it’s just so zen. You’ll have to find your own words for it after you ride it. Emerge at the top at Callahan’s Lodge, a local landmark for decades, where you can decide to turn around and zoom down the old highway or head up toward Mt. Ashland Ski Area, where the more strenuous climbing awaits.