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. Serene Las Gallinas

    A serene stroll alongside marshland, passing ponds and grasses frilled in seasonal wildflowers, with Mount Tam a beacon in the background … how nice. As part of the esteemed Bay Trail, San Rafael’s Las Gallinas Valley Birding Loop and Wildlife Ponds comprises about 3.5 miles of wide-open trail.

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  2. Paint Brushy

    This time of year you’ll have good reason to head for the hills—the electric-green rolling hills of Brushy Peak Regional Preserve in Livermore. This 4.5-mile loop hike is like stepping into a plein air painting.

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  3. Sponsored

    2025 POST Wildflower Walks

    Get flower empowered! POST’s complimentary 2025 Wildflower Walks guide blooms with the best places to see a variety of florals across the Peninsula and South Bay this spring.

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  4. 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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Trending Stories SoCal

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  1. Sponsored

    Weekend in Reno Tahoe

    Weekend plans? Reno Tahoe! Just a few hours by car or a short flight away, Reno Tahoe springs to the moment with great ways to combine adventure and relaxation in its beautiful mountains-meets-desert setting.

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  2. Hiker walking along the North Bluff Trail on Santa Cruz Island, Channel Islands National Park

    Purely Wild

    Channel Islands National Park lives up to its nickname as “North America’s Galapagos.” This less-traveled national park is an undeveloped and isolated series of five dramatic and distinct islands reached by boat. Hike the largest of the islands, Santa Cruz.

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  3. Woman hiking the South Kaibab Trail in the Grand Canyon

    Truly Grand Day Hike

    One of the best spring day hikes in the Grand Canyon? See layer upon layer of the park’s grandeur—including the river—on this 3-mile (one-way) journey to Skeleton Point via the South Kaibab Trail.

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  4. A woman stands amid an array of yellow and purple flowers at Descanso Gardens in Los Angeles

    Petal Paradise

    Tulips, lilacs, and daffodils—flower power is in full bloom at Descanso Gardens in La Cañada Flintridge. Sprawling across 150 acres surrounded by mountains, the gardens are putting on their best show right now.

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