All Roads Lead to Rogue

Rogue Valley Road Trip in Southern Oregon

Hobart Bluff Rogue Valley Oregon Road Trip

We have an idea for your next road trip: Go Rogue! The Rogue Valley in beautiful Southern Oregon has some of the state’s best hiking, swim holes, and wineries, and the charming historic towns of Ashland, Medford, and Jacksonville. Get on the road to Rogue Valley!

National Monuments Not to Miss

Hobart Bluff hike

Cascade-Siskiyou National Monument sits at the convergence of the Cascade, Klamath, and Siskiyou mountain ranges. So in other words, it’s glorious! Hike to the oh-so-photogenic Pilot Rock—an ancient volcano so distinct it’s a beacon for road trippers on the I-5. Part of the trail intersects the Pacific Crest Trail.

Climbing to the top of Pilot Rock is a steep scramble so you’ve gotta be careful (and hey, it’s still cool if you just hike to its base!). For a less steep way to get amazing views, do the 1.5-mile (one-way) hike to Hobart Bluff. You’ll be rewarded with a round-the-compass view of the Rogue Valley. Another great place for exploring: Oregon Caves National Monument. Of course, there are awesome caves—but there’s also really good hiking!

Best Southern Oregon Road Trips

Rope Swing, Swim Spots, Crazy Rapids.. Rogue River!

Rogue River Rafting

From lazy river afternoons and rope swing hijinks, to whitewater rafting and wild and scenic jetboat tours, the Rogue River is the heartbeat of the region. You can float this river on a DIY inflatable kayak, or go with a professional outfitter for Class II and III rapids. Here are some DIY raft rental + small group guided outfitters: Rogue River Day Trips (kayak & raft rentals); Rogue Rafting; Raft the Rogue; Indigo Creek Outfitters; Noah’s Rafting Trips; Hellgate Jetboats.

Bonus: Family-owned Galice Resort is a Rogue River area staple offering raft rentals and trips. They also have log cabin stays and a spacious deck overlooking the river—perfect for pairing an Oregon micro-brew with a home-cooked meal.

Best Southern Oregon Road Trips

The Grape Outdoors

If you love pairing your outdoor adventures with wine explorations, then you’ll love the Rogue Valley! This Southern Oregon AVA has four Wine Trails that are relaxed and fun. Bear Creek Trail, Oregon’s southernmost region of the Rogue Valley AVA, was named one of the World’s 10 Best Wine Travel Destinations by Wine Enthusiast. Applegate Wine Trail was perfectly summed up by Sunset magazine as “Wine Country, the way it should be.” If you like pairing bold reds and national parks, the Upper Rogue Wine Trail is located just an hour south of Crater Lake National Park. And for the most sensational pinots, head to the charming gold-rush-era town of Jacksonville and explore the Jacksonville Wine Trail.

Best Southern Oregon Road Trips

Small Towns, Big Parks!

Ashland Oregon downtown dining

Southern Oregon is home to three beautiful historic towns: Ashland, Jacksonville, and Medford. And they all have amazing parks for hiking and biking. Ashland’s crown jewel, Lithia Park, is located close to all the cool cafes and the grounds of the famous Oregon Shakespeare Festival. Ashland Creek runs through its 100 acres of terrain, also known as the emerald urban oasis. In Jacksonville, there’s more than 16 miles of trails in Jacksonville Woods.

With several options as starting points, it’s easy to go on a hike right from downtown. And Medford’s Prescott Park is pure hiking and mountain biking heaven. Its 1,740 acres of paved and unpaved terrain offer unbeatable views of the Rogue Valley. The park’s crowning glory, Roxy Ann Peak, is a wowing panorama of the valley and surrounding mountains, including Mount Shasta, Mount Ashland, and Mount McLoughlin.

Best Southern Oregon Road Trips

Where to Lodge and Camp

From boutique hotels and inns, to cabins, lodges, and camping, here are some places to stay in Southern Oregon.

Ashland

Ashland Springs Hotel

Peerless Hotel

Willow-Witt Ranch

Jacksonville

McCully House

Jacksonville Inn

Medford

Inn at the Commons

Grants Pass

Weasku Inn

The Lodge at Riverside

Galice Resort

Morrison’s Lodge

CAMPING

Jackson County Parks

Josephine County Parks

Trending Stories NorCal

View all Stories
  1. Sponsored

    The 2025 Hiking Calendar Is Here!

    Ready to make hiking part of your New Year’s wellness plan? Get the all-new 2025 Hiking Calendar courtesy of Peninsula Open Space Trust (POST).

    View
  2. Most Peaceful Hike of All

    Is this the most peaceful one-hour hike in the Bay Area? It's got our vote! Lake Lagunitas is the smallest lake in a series of five found on the north side of Mount Tam, so it’s got that tiny but mighty charm. Do a 1.5-mile loop around the lake's shore-hugging trail.

    View
  3. Two hikers at Bear Creek Redwoods Regional Preserve on a new trail.

    New Trails at Bear Creek

    Looking for new trails? Bear Creek Redwoods Open Space Preserve has added 170 acres of forest, grassland, and historical sites. Hike this 3.5-mile loop through the new addition.

    View
  4. Woman swimming in Carson Hotsprings natural thermal pool

    Hot Springs, Naturally

    Thermal spring waters are famous for their curative, relaxing elements, and Reno Tahoe is filled with them! Sink into these amazing thermal respites for a wellness super soak.

    View

Trending Stories SoCal

View all Stories
  1. Animal Encounters

    Located where Redding’s famous Sundial Bridge overlooks the Sacramento River, Turtle Bay Exploration Park is 300 acres of gardens, a museum and playground, aquarium, and unforgettable up-close animal encounters!

    View
  2. Weekend Sherpa Podcast
    Sponsored

    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!

    View
  3. Locals' Feature: Max Smith of Moment Skis

    Meet Max Smith, VP of Moment Skis in Reno, Nevada. Moment is the largest ski manufacturer in the US and you can see how their innovative and artistic skis are made by visiting Moment Skis headquarters in Reno. The Factory is where the magic happens, so drop in for a visit and say hi to the team, including employee dogs who are on quality control.

    View
  4. Woman hiking down the stairs to Coast Royale Beach in Orange County

    Secluded Royale

    Panoramic coastal views and a killer leg workout combine on this 2.7-mile (round-trip) out-and-back hike to secluded Coast Royale Beach in Orange County

    View