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Southern Oregon is a year-round destination for everyone from adventurers to culture and history lovers. Unlike Oregon’s coastal destinations, it boasts lots of sunshine to go along with the temperate climate. Take this Oregon road trip on an amazing 365 mile loop from Klamath Falls to experience it yourself.

To get to Klamath Falls, hop in a car in Portland or alternatively, board the train from Union Station in downtown Portland. The train lets you relax on the scenic 7.5 hour Amtrak experience. Rent a car once there and follow this suggested route to discover just some of the magic to be found in southern Oregon.

First Road Trip Stop: Ashland, Oregon

 Wildlife near Ashland, Oregon

Wildlife near Ashland, Oregon. Photo by Sean Gordon/Bureau of Land Management, Oregon. Edited and reused under a CC BY-SA 2.0 license.

Once you have your car in Klamath Falls, head 60 miles northwest and make Ashland your first stop. Ashland is only 14 miles from the California border, boasts 300 days of sunshine/year and is best known for arts and entertainment.

Plan your trip during the Oregon Shakespeare Festival that runs from March to October and offers over 900 performances. Expect non-traditional Shakespeare along with a variety of other plays and events. You can view the website for specific dates, shows running and tickets in advance. Year round musicals are performed at the Oregon Cabaret Theatre, an intimately restored, historically registered former church.

When night falls, stay at Ashland Springs Hotel for walkable access to all the theatres and many restaurants. Recommendations? Try Greenleaf for breakfast and lunch, or the Peerless Restaurant and Bar to linger over an elegant dinner.

You can easily spend a few days in Ashland, taking a few hours to hike around Lithia Park or for more challenge, find nearby access to Siskiyou National Forest, Grizzly Peak and the Pacific Crest Trail, a famous 2600 mile hike from Mexico to Canada (think Camino del Santiago times five).

Unique Landscapes and the Southern Oregon Wine Industry

See many Oregon vineyards on your Oregon road trip.

See many Oregon vineyards on your Oregon road trip. Image by Tim Mossholder from Pixabay

Ashland has a unique landscape, surrounded by both forest and bare hills. Drive up the scenic Dead Indian Memorial Road to Willow Witt Ranch, a 445 acre sustainable off the grid ranch owned by Suzanne Willow and Lanita Witt. They offer everything from camping and wall tents, to a modern three bedroom house for those craving solitude. As well, they run an organic farm with land that’s perfect for birding and hiking (book a tour with their pack goats).

Southern Oregon has its own wine industry, with five designated AVA’s – Umpqua and Rogue Valley being the largest. Thanks to the topography creating unique mesoclimates, over 70 grape types are currently grown. Pinot noir is still the most planted, but warm weather varietals, including tempranillo, viognier, Syrah and malbec are creating local buzz.

North to Jacksonville, Oregon

Historical hotels are abundant in quaint small towns (Jacksonville Inn)

Historical hotels are abundant in quaint small towns (Jacksonville Inn). Photo by BJ Oudman.

From Ashland, you can head north to the picturesque gold mining town of Jacksonville with its preserved buildings, quaint shops and many restaurants. Check out the Britt Festival schedule to attend an outdoor concert in an amphitheatre in the downtown Jacksonville Woodlands. During the day, walk to the panoramic viewpoint to take in Applegate Valley and see Madrone trees with their peeling bark that only grow at high and dry elevations.

You can take the I5 and get to your destination quickly, but block highways on your GPS to follow the more scenic route.

Jacksonville to Grants Pass

Multi-use Bolt Mountain Trail near Grants Pass

Multi-use Bolt Mountain Trail near Grants Pass. Photo by Bureau of Land Management, Oregon. Edited and reused under a CC BY-SA 2.0 license.

Drive north along Applegate Trail through vineyards and rolling hills to Grants Pass, which touts itself as Oregon’s white water rafting capital. Indeed, you can take river trips lasting from a few hours to a few days. A four season town, Grants Pass promises a moderate climate, little rain and lots of sunshine.

Near Grants Pass you’ll also find the certified organic Rogue Creamery Farmstand. Take a stop here for the best grilled cheese sandwich and tomato soup, which will be warranted after witnessing their robotic milking machines, Charlie and Matilda, at work.

Grants Pass to Roseburg

Taking the road less travelled on an Oregon road trip near Roseburg

Taking the road less travelled on an Oregon road trip near Roseburg. Photo by BJ Oudman.

From Grants Pass, the I5 is the only viable, but surprisingly beautiful, route unless you have lots of time to cross Coast and Cascade Range summits to get to Roseburg. Roseburg, you’ll find, is a larger centre with a redeveloped historical downtown. It’s also a good place to stock up on supplies before heading to the National Parks for a few days of hiking, biking and just enjoying nature.

Spend the night at the Hampton Inn for its convenient location, but book dinner at the National Historic Registry acclaimed Parrot House. Dine in the pavilion while enjoying live music or outdoors on the manicured grounds after enjoying a cocktail at the Reform Bourbon Bar.

Roseburg to Steamboat Inn

Rushing waterfall in Umpqua National Forest

Rushing waterfall in Umpqua National Forest. Photo by BJ Oudman.

Leaving Roseburg, head west through Umpqua National Forest, taking the Rogue Umpqua Scenic Byway toward Crater Lake. Since the journey is not just the destination, plan an overnight stay at the legendary Steamboat Inn.

The Inn gets its name from the nearby Steamboat Creek. While gold and silver were mined in the 1860s from the Bohemia Mining District close to Steamboat Creek, the local gold runs more to heavy runs of summer steelhead, a type of rainbow trout.

Indeed, whether you prefer to cast a line for steelhead on the Umpqua River or hike to a thundering waterfall, you’ll enjoy your stop at Steamboat Creek on your Oregon road trip. And there’s no doubt a night spent in a streamside cabin or a hideaway cottage with dinner at the onsite restaurant is a treat for everyone.

Steamboat Inn to Crater Lake North Entrance

Crater Lake in Oregon.

Crater Lake in Oregon. Image by Art Bromage from Pixabay

Continue along highway 138 to the spectacular north entrance (closed in the winter) of Crater Lake. It’s the deepest lake in the US resting in the belly of a dormant volcano, and one of Oregon’s 7 Wonders. The many names it has been known as reflect its mystery: Mysterious Lake, Lake Majesty, Lake Mystery, Great Sunken Lake and Blue Lake.

Avid cyclists can cycle Crater Lake’s 33 mile rim in the right season, but other activities include hiking, cross country skiing, snowshoeing or even a boat tour. Later on, you’ll find a few motel options available in the park, but campers will be delighted by available sites (just book ahead).

Back to Klamath Falls

Crater Lake - Mt Mazama, Oregon.

Crater Lake – Mt Mazama, Oregon. Image by ArtTower from Pixabay

Complete the route by leaving the south entrance of Crater Lake back toward Klamath Falls. Take highway 140 to access scenic rest points along Upper Klamath Lake or detour to Lake of the Woods. Return your car and use the train ride to Portland to make plans for your return visit to the magic that is Oregon.

Plan Your Oregon Road Trip

Check out TravelOregon on the Web for more information on each of the destinations.

When planning your trip, keep in mind the more numbers in a highway (example, 138 compared to 5), the longer it will take, but the more scenic the drive. Approximate driving distances/times (see the Google map below as well):
Klamath Falls to Ashland – 65 miles, 85 to 105 minutes
Ashland to Jacksonville – 17 miles, 30 minutes
Jacksonville to Grants Pas – 35 miles, 50 minutes on highway 238 (Applegate Trail)
Grants Pass to Roseburg – 69 to 125 miles, 75 to 240 minutes
Roseburg to Steamboat Inn – 38 to 48 miles, 45 to 60 minutes
Steamboat Inn to Crater Lake North Entrance- 50 miles, 60 minutes
Crater Lake South Entrance to Klamath Falls – 60 to 80 miles, 75 to 95 minutes

About the Author

BJ Oudman BJ Oudman has a passion for travel that has led her to explore the local lifestyle, food and markets in over 25 countries. Based in Calgary, Alberta, she has shared stories for over ten years in many publications. They include Savour Calgary, City Palate, Culinaire, Impact, Globe & Mail, International Living and Travel & Style. She holds a diploma from the International Sommelier Guild as well as a Bachelor of Science in Physical Therapy from the University of Alberta.

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