Racing in a bowl: Hellyer Park Velodrome
Southern Oregon Grand Tour: Medford

Southern Oregon Grand Tour: Ashland

Last October Cycle California! Magazine took to the open road to explore the bicycle wonderland that is north of the border: Oregon. One of us won a drawing for a couple nights stay in Medford, Oregon, along with some freebies like a couple of meals.

Since we were planning to visit clients in the area, we thought we'd add a few more cities to our itinerary and do a grand tour of the region. For those like me who are geographically challenged when it comes to Oregon, the trip was an eye-opener. This area of Oregon is the Rogue Valley, located west of the Cascade Mountains and to the north of the Siskiyou Mountains. It is separated from the west coast by Southern Oregon's Coast Range. This valley has a mild climate (with hot summers, somewhat like California's Central Valley).

Mt. Ashland & Trails

Loaded down with four bikes bikes (one mountain bike and one road bike each) we made our way along I-5 north to our first stop in Ashland. Although the town is more well-known for its Shakespeare Festival, the area has multiple opportunities for epic bike rides.

Mt. Ashland
Mt. Shasta on a fall day from Mt. Ashland

Before we reached our destination hotel, the Ashland Hills Hotel & Suites, on the outskirts of the trendy downtown, we made a detour up Mt. Ashland, where mountain bikers and other lovers of singletrail trails can indulge in their passion on a mountain that looks out at its big sister to the south, Mt. Shasta. A stretch of the Pacific Crest Trail, a hikers-only trail, is located on Mt. Ashland as well.

Because the summer crowds were mostly gone and the ski season hadn’t started up yet, the mountain park was relatively empty. There, on the side of the mountain that includes a ski bowl, we sat at an empty picnic table and ate a late lunch on food we brought, munching on pesto pasta salad, fresh fruit and homemade sandwiches and gazed at the north face of Mt. Shasta, just over the border.

Uphill Mountain Biking

The town of Ashland sits (more or less) at the foot of Mt. Ashland. From Lithia Park in downtown Ashland, very strong mountain bikers can find a road that becomes a trail that will take them to the parking lot next to our lunch spot on the mountain. The Ashland Loop Road is a trail starts at Lithia Park and climbs from an elevation of 1,200 feet above sea level to 6,600 feet in about 12.5 miles.

Since we were already at the top of the mountain, I thought about taking my bike and riding down to the town, but that would have meant Bob would have to drive alone. I was the navigator, so I abandoned that idea.

We hopped into the truck and made our way to the Ashland Hills Hotel and Suites, where we put our heads on fine pillows and stretch out in a comfortable suite before continuing our grand tour north. Earlier this year, the hotel received the official Bike Friendly designation by Oregon's tourism board, Travel Oregon (

Bear Creek Greenway
Bear Creek Greenway entrance

Rogue Valley Ride

Next day we pulled our bikes off the truck and spent the day exploring Ashland by road bike. We rolled through town to the Ashland Dog Park where we started our journey north on the Bear Creek Greenway.

As its name suggests, this north/south bike path follows Bear Creek, a tributary of the Rogue River. As it winds through the Rogue Valley, the Greenway links the towns of Ashland, Talent, Phoenix, Medford, and Central Point, a distance of about 18 miles from end to end. The paved trail is mostly off the road, enabling bikers to go without interrupting their ride with stops. It also rolls along I-5, which makes it a bit of a noisy experience.

If you're in the area and want some riding buddies, the local bicycle club, Siskiyou Velo (, has a Slo Mo ride that sometimes goes out along the Bear Creek Greenway.

In-town Exploration

We turned around after the town of Phoenix and made our way back into Ashland for lunch, then spent the rest of the afternoon exploring Lithia Park, a 93 acre open space with miles of paths for walking (no bikes allowed on trails, but there are many places to lock your bike if you want to explore on foot). The park meanders along Ashland Creek and has a Japanese garden, two duck ponds, a formal rose garden, and groves of sycamore trees.

Note: Dogs aren't allowed in Lithia park. If you do have a four-legged companion with you, the City of Ashland's website ( has a page with a listing of dog-friendly parks.

Fall is in the air at Lithia Park, Ashland
Fall is in the air at Lithia Park, Ashland

Almost Heaven, Scenic Bikeways

Another road ride you can do out of Ashland, much more challenging than the Bear Creek Greenway, is along the Cascade-Siskiyou Scenic Bikeway, a state-designated bike ride. At about 55 miles or so, this route incorporates 5,000 feet of winding elevation gain through oak-studded rolling hillsides as it climbs to the 4,551 foot Greensprings Summit. Riders roll past Hyatt Reservoir then climb a final three miles to the alpine meadows of Lily Glen and Buck Prairie.

After Buck Prairie, it's a downhill thrill ride back to Ashland. You can find a detailed map and a road cue sheet of the Cascade-Siskiyou Scenic Bikeway route at the Ride Oregon Ride website, Into camping? Make it a two-day outing and camp at Hyatt Reservoir or Howard Prairie Lake. You can find information on camping at state parks at

There are 15 of these Scenic Bikeways around the state, and to learn more about them, the Ride Oregon Ride website can help.

If you need help planning a grand adventure like ours, Travel Oregon has trip tips and suggestions.

Another approach to exploring the area is through a bike tour company. One of our magazine clients, Via Bike Tours (, has organized multi-day tours in this part of Southern Oregon.

Eats & Drinks

Caldera Brewery & Restaurant, (541) 482-4677, offers a view of Mt. Ashland and approximately 40 beers on tap in addition to delicious food made with locally sourced ingredients. There is bike parking galore and a dog-friendly patio. 590 Clover Ln., Ashland

Caldera Tap House, (541) 482-7468, Caldera Brewery's sister location, is in downtown Ashland, with a large outdoor three-tiered deck that overlooks Ashland Creek. 31 Water St., Ashland.

Brothers' Restaurant, (541) 482-9671, breakfast and lunch, with breakfast served all day. 95 North Main St., Ashland.

Lark's Home Kitchen Cuisine in the Ashland Springs Hotel, (541) 488-5558, offers exquisite meals with locally sourced ingredients. 212 East Main St., Ashland.


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We did have fun up there in Medford and Ashland. We're trying to plan a trip back up there, but I don't see it happening this year, unfortunately. So glad you liked the posts, Juli!


Enjoying the posts about Ashland and Medford - visited many times for the Oregon Shakespeare Festival. Hopefully you and Bob enjoyed it as much as I do.

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