Crater Lake Resort glamp tent near Crater Lake National Park

Road Trip to Remember

Your next road trip shouldn’t even be a question. It’s got to be Southern Oregon. Hike the natural landmark of Table Rocks, paddle in the serenity of the Cascades, see the best urban parks and greatest waterfalls, go glamping near Crater Lake National Park, and enjoy bucolic food + wine trails. Here’s an itinerary from our recent adventure to help you map out your very own Southern Oregon vacation.

Week: 07.12.2023
Regions: Northern & Southern CA

Zen & the Art of Kayaking

Kayak Near Klamath Falls and Stay at Crater Lake Resort

Two kayakers on Upper Klamath Basin on tour with Sky Lakes Wilderness Adventures
Glamp tent at Crater Lake Resort near Klamath Falls Southern Oregon
Kayakers on the Bird Watching Tour at Upper Klamath Basin with Sky Lakes Wilderness Adventures
It’s the most meditative and relaxing experience you’ll ever have on a kayak. Yes, you read that right, a Zen experience on a kayak. It all happens in beautiful Klamath County when you head out on a guided tour with Sky Lakes Wilderness Adventures.
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Basecamp to Hiking Beauty

Hike Table Rocks and Roxy Ann Peak in Medford

Hikers at Prescott Park in Medford
Hiker at Upper Table Rock near Medford
Hikers on the plateau of Upper Table Rock in Medford
Located in the beautiful Rogue Valley, Medford is a road-trip basecamp for some stellar hiking and sightseeing, including a must-visit natural landmark, The Table Rocks.
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Valley of Earthiness, River of Rogue Dreams

Wine and Food Along the Applegate Trail in Grants Pass Oregon

Outdoor photo of Pennington Farms in Grants Pass Southern Oregon
A photo of a jam jar from Pennington Farms on the Rogue Valley Food Trail in Southern Oregon
Troon Vineyards in Southern Oregon
Enchanted Forest Trailhead in Grants Pass Southern Oregon
Driving from Medford to Grants Pass—and passing through the historic town of Jacksonville— get ready for farm charms and pure pastoral beauty along the quiet roads of Applegate Valley, where the Rogue Valley Food Trail and forward-thinking, sustainable wineries await.
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Coming Up, Roseburg!

Explore Roseburg Wineries and Downtown

woman standing at a colorful butterfly mural amid the mural art project in Roseburg
A group of friends sitting around a table overlooking the vineyard at Melrose Vineyard near Roseburg Southern Oregon
A man and woman enjoy a game of ladder toss on the grounds of Abacela Winery near Roseburg
Make your way to Roseburg in Southern Oregon, where downtown’s food scene and vibrant mural walk await. Follow it up with some wine tasting in Roseburg’s Great Umpqua region.
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Watson in a Name? A lot, Sherlock!

Hike to Watson Falls in Southern Oregon

Watson Falls in Southern Oregon along the Highway of Waterfalls
Two people at the overlook and watching Watson Falls in Southern Oregon
A hiker crosses a bride enroute to Watson Falls in Southern Oregon
Up close picture of Watson Falls in Southern Oregon
The #1 rule of the unofficial waterfall club? You cannot take a road trip through Southern Oregon and skip the Highway of Waterfalls. This stretch of Highway 138 east of Roseburg along the Umpqua River is a watery marvel that’s lovely year-round.
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Trending Stories NorCal

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  1. All right, Almaden!

    Take a trip through time on this 5-mile loop in Almaden Quicksilver County Park. Explore the ruins of an old cinnabar mine and enjoy the first hints of wildflower season.

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  2. Waterfalls and Wine Pours

    Cooler temps, green hills, and the return of our magnificent waterfalls! This family-friendly 2-mile hike at Uvas Canyon County Park in Morgan Hill is a great way to get the most out of a short hike post-rain.

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  3. Woman hiker is climbing up the ladder in the Steep Ravine section of the Dipsea Loop Trail on Mount Tam

    Misty on Mount Tam

    Mount Tam’s 3.9-mile round-trip Steep Ravine and Dipsea Trail Loop weathers the wets and wilds with some confidence, sheltered in parts by redwoods, and wowing with a waterfall.

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  4. Mile-Long Cataract Club

    In winter after heavy rains, the north flank of Mount Tam glows with flows. The nearly mile-long series of waterfalls—Cataract Falls—transforms into a supercharged spectacle. Starting at Alpine Dam, a 1.6 mile (one-way) narrow trails threads through redwoods and ferns along Cataract Creek.

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Trending Stories SoCal

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  1. Peace Labyrinth

    Hidden in LA’s historic West Adams district, the Peace Awareness Labyrinth & Gardens is a welcome respite from the norms of urban noise.

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  2. Weekend Sherpa Podcast: Take It Outside

    Adventure for your earbuds. What's new in the world of the outdoors? Listen to Weekend Sherpa co-founders discuss local hikes, beaches, bike rides, camping spots and all kinds of travel and adventure in California and beyond!

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  3. Hikers sitting on a large rock slab next to Three Sisters Falls in Cleveland National Forest Southern California near Julian

    Three Sisters

    Good things come in threes at this hike to a lovely trio-tiered waterfall in Cleveland National Forest. The 4.25-mile out-and-back hike rambles among rolling hills, with rocky mountain views as switchbacks take you down to a lush canyon and the falls.

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  4. People gathered around a tree at an LA Park as part of the Tree Tour led by Stephanie Carrie

    LA's Tree Tour

    Los Angeles is famous for its iconic palm trees but did you know that LA is home to one of the most diverse urban forests in the world? With over 1,000 different tree species lining its streets, LA offers a unique urban canopy waiting to be explored. One of the best ways to discover it is by joining a Tree Tour

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