Rolling pavement and challenging turns make Oregon State Route 66 a favorite destination for sport touring riders. Image © American Sport Touring.

Destination Oregon SR-66

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If you’re a sport touring enthusiast looking for an exciting destination road, check out Oregon State Route 66. This captivating stretch of twisting road offers a blend of historic charm, stunning landscapes, and exhilarating riding experiences that are sure to leave you wanting more. Spanning approximately 60 miles, this route connects the picturesque Oregon cities of Ashland and Klamath Falls, each offering unique attractions and rich history.

A Motorcyclist’s Dream

For motorcyclists, the allure of Oregon State Route 66 lies in its diverse terrain and engaging roadway. As you embark on your journey heading from Ashland to Klamath Falls or the other way around, you’ll encounter a series of tight curves, steep climbs, and descents that make for an adrenaline-pumping ride. The road meanders through the Siskiyou Mountains, providing spectacular views of dense forests, rolling hills, and pristine rivers.  

The twists and turns of Route 66 demand focus and skill, making it an ideal route for sport touring enthusiasts who relish a challenge. Traffic is generally light, allowing for an uninterrupted and immersive riding experience. The roadway’s well-maintained pavement ensures a smooth ride, though it’s always wise to stay alert for occasional wildlife crossings or fallen rocks.

Map of SR-66.
Map data ©2024 Google. Oregon State Route 66 between Ashland and Klamath Falls.

Keep in mind that this route crosses several snow zones, meaning two things.  First, there’s a high probability twisty road are ahead; and secondly, expect a climb into higher elevations and correspondingly colder temperatures.  If riding in early spring or late fall, gear-up accordingly.


Ashland: A Historic Gem

The journey passes though Ashland, a city renowned for its vibrant arts scene and historic charm. Nestled in the Rogue Valley just west of Interstate-5, Ashland is home to the internationally acclaimed Oregon Shakespeare Festival, which draws theater lovers from around the globe. The festival, held from February to October, showcases an impressive array of Shakespearean plays and contemporary productions, making it a must-visit for cultural enthusiasts.

Ashland festival site.
The Shakespeare Festival, running annually from February to October, brings visitors to Ashland. Image © American Sport Touring.

In addition to its theatrical offerings, Ashland boasts a wealth of historic landmarks. Stroll through the downtown area to admire beautifully preserved Victorian-era buildings, quaint boutiques, and cozy cafes. The Ashland Historic Railroad District offers a glimpse into the city’s past, with its charming architecture and informative plaques detailing the area’s significance.

Nature lovers will find solace in Lithia Park, a 100-acre oasis in the heart of the city. The park features lush gardens, serene ponds, and scenic walking trails that invite visitors to unwind and connect with nature. Don’t forget to sample the park’s namesake, Lithia water, from one of the historic fountains scattered throughout the area.

Scenic Beauty Mixed With Adrenaline

As you ride from Ashland heading east on Route 66, the landscape transforms into a tapestry of natural beauty. The road ascends into the Siskiyou Mountains, offering panoramic views of the surrounding wilderness. The air grows crisper as you climb higher, and the scent of pine invigorates your senses.

Motorcyclists of all stripes will revel in the technical aspects of the ride, with numerous switchbacks and hairpin turns that test your skills and keep the adrenaline pumping. Each curve unveils a new vista, from dense forests to open meadows and sparkling streams. Keep an eye out for Emigrant Lake, a popular spot for boating, fishing, and picnicking, located just a few miles southeast of Ashland.


The journey continues through the rural community of Pinehurst, a peaceful enclave surrounded by towering trees and verdant fields. The Pinehurst Inn, a historic bed and breakfast, offers a charming spot to rest and enjoy a tasty meal before continuing your adventure.

Klamath Falls: Nature’s Playground

As you descend from the mountains and approach Klamath Falls, the landscape gradually shifts to wide-open spaces and sprawling farmlands. Klamath Falls, known as the “City of Sunshine,” boasts over 300 days of sunshine per year, making it a perfect destination for outdoor enthusiasts.

Klamath Falls has a rich history rooted in the timber and railroad industries. The Klamath County Museum offers fascinating exhibits covering the region’s past, including Native American artifacts, historic photographs, and displays tracing the area’s development.

Klamath Falls street clock
Enjoy an afternoon break in Klamath Falls, Oregon. Photo by Gary Halvorson.

One of the city’s standout attractions is nearby Klamath Lake, the largest freshwater lake in Oregon. Klamath Lake is a haven for birdwatchers, with over 350 species of birds making their home in the surrounding wetlands. Rent a kayak or paddleboard to explore the lake’s mostly tranquil waters and observe the abundant wildlife.

For a unique historical experience, visit the Baldwin Hotel Museum, housed in a former luxury hotel built in 1906. The museum offers a glimpse into early 20th-century life, with period furnishings, vintage clothing, and other intriguing artifacts.


Oregon SR-66: A Perfect Blend of Adventure and Tranquility

Oregon State Route 66 offers sport touring motorcyclists an unforgettable journey through some of the state’s most captivating landscapes. From the cultural richness of Ashland to the natural splendor of Klamath Falls, this route is a perfect blend of thrilling riding and serene beauty.

Oregon SR-66.
Spanning nearly 60 miles between Ashland and Klamath Falls Oregon, State Route 66 delivers exciting curve after curve. Image © American Sport Touring.

As you navigate the twists and turns of the Siskiyou Mountains, you’ll find yourself immersed in the raw beauty of Oregon’s wilderness. The road’s challenging curves and elevation changes provide an exhilarating experience for seasoned riders, while the light traffic ensures a peaceful and uninterrupted ride.

Whether you’re exploring historic landmarks, enjoying outdoor activities, or simply taking in the stunning scenery, Oregon State Route 66 promises an adventure that will stay with you long after the ride is over. So, gear up, hit the road, and let the allure of Route 66 take you through an unforgettable motorcycle sport touring experience in the heart of Oregon.

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