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. Cinematic Sonoma

    Longer days. Golden light. Wildflowers in bloom. It’s the perfect moment to plan your spring escape to Sonoma for the Sonoma International Film Festival, March 25–29. No fuss. No sprawl. Just films, friends, fresh air, and that unmistakable Sonoma glow.

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  2. Hike Pescadero Marsh Natural Preserve

    Mellow in the Marsh

    Beach, birds, ice plant popping purple flowers: That’s a hiking slam dunk! Hike about 2 miles at Pescadero Marsh Natural Preserve using their easy to navigate (well-signed) Sequoia Audubon Trail.

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  3. A man is looking through his binoculars at sunrise at the Bayland Nature Preserve in Palo Alto

    Baylands Bird & Art Loop

    Combine an outdoor art walk and wildlife sightings at the Baylands Nature Preserve in Palo Alto. This 5-mile loop through Byxbee Park and the Emily Renzel Wetlands features striking installations by artists Peter Richards and Michael Oppenheimer—where the landscape itself becomes part of the canvas.

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  4. Big Burdell!

    If you’re gonna go big on a hike, make it at Marin County’s biggest open space preserve, Mount Burdell. And go to the summit. You’ll be sharing the trail with grazing cows, seasonal poppies, and beautiful birds on this 5-mile (round-trip) adventure.

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  1. Sponsored

    Warm Up to Winter in Reno Tahoe

    2026 is just getting started, but there’s one place already rising to the top as the best for adventure and relaxation: Reno Tahoe. The awe—and ahhhs—begin as soon as you arrive. G

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  2. Eat, Sleep, Beach, Repeat

    For an ultra-relaxing getaway where you can sit back and soak in some nature and nurture, head to Mendocino and follow this eat, beach, sleep, repeat itinerary (you won't regret it!) ...

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  3. This Skunk Doesn’t Stink!

    All aboard for a ride through history—and through air scented with redwood, dewy ferns, forest-fresh breeze, and a bonus snack and beverage bar, fire pit, and short hike. The World-Famous Skunk Train delivers in every category: scenery, greenery, and towering redwoods.

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  4. A woman standing at the pond's edge at Ernest B Debs Regional Park in Los Angeles. Trees are making reflections on the pond.

    Urban Oasis Loop

    Home to the city’s Audubon Center, Ernest E. Debs' 282-acre park features a robust network of hiking trails and surprising wildlife diversity. More than 140 bird species have been spotted here. Birdwatcher or not, this 2.5-mile route makes for a gorgeous outing.

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