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Road Trip Adventures on Interstate 5 in Southern Oregon

Enjoy great eats and cultural stops along the route from Ashland to Roseburg.

Seasoned travelers headed through Interstate 5 in Southern Oregon know to take it slow and enjoy some time in many unique communities along the way. Here you’ll encounter walkable small towns, award-winning restaurants, parks, museums and more — all surrounded by lush forests and scenic mountains. Try a few of these itineraries designed to showcase top spots for every kind of road-tripper.

Oregon Shakespeare Festival grounds (Photo by Jak Wonderly)

Gardens and Theater Road Stop in Ashland 

Hop off the highway near the Oregon-California border to tour Ashland, home to theaters, restaurants and outdoor recreation. Stroll through the 100-acre Lithia Park and experience the beauty of the Ashland Japanese Garden, which opened in 2022. Try walking counterclockwise through tea gardens, a bamboo forest, a waterfall, and a traditional sand and stone garden. No matter what the weather holds, you can enjoy a matinee show at the Oregon Cabaret Theatre, featuring classics like “Little Shop of Horrors.” Afterward, savor street tacos, spicy mango margaritas and more at Taqueria Picaro, just off the plaza in downtown Ashland. 

Forage Coffee

Food Lovers’ Bounty in Medford

About 13 miles north of Ashland, stop off in the bustling town of Medford. Shaped by pear orchards and vineyards, Medford is the urban heart of the Rogue Valley. Encounter the thriving and abundant Thursday Rogue Valley Growers and Crafters Market with a choice selection of the Rogue Valley’s top food trucks, fresh fruits and vegetables from local organic farmers, and handcrafted gifts from Northwest artisans. Stroll down the street to Forage Coffee — recognizable immediately as a retro gas station turned hip cafe — and enjoy a cappuccino made with locally roasted beans from Case Coffee Roasters. If you have time, go for a quick hike at Roxy Ann’s Prescott Park, where you’ll find native wildflowers in spring and panoramic views of Mt. Ashland, Table Rocks and Mt. McLoughlin. 

Grants Pass mural

Vintage Classics in Grants Pass 

You won’t regret a stop in the friendly town of Grants Pass, a spirited home base for Rogue River recreation about 30 miles north of Medford. Designated as a Historic District for its remarkable original buildings and storefronts as well as abundance of public art. Explore this vibrant area with the Public Art Walking Tour. You can find vintage housewares, clothing, books and more in the antique shops downtown, including the Elegance Antiques, Old Town Antique Mall and The Red Canary Mercantile. Indulge in a burger and fries at The Haul, located in a quintessential pub setting with a rustic bar, a wood-fired pizza oven. If you’re looking for a craft beverage, stop in at Climate City Brewing in the historic Grants Pass Brewery building or for a cocktail at their neighbor, Steam Distillery. End your visit with a lesson at The Glass Forge, where you can create a bowl, a paperweight or an ornament in a 5,000-square-foot glass-art gallery.

Wolf Creek Inn

Historic Wolf Creek Inn for a Good Old Time

Between Grants Pass and Roseburg lies the tiny community of Wolf Creek. Step back in time at the Historic Wolf Creek Inn to learn about this former stagecoach stop established in 1883, the oldest continually operated hotel in Oregon. Surrounded by the Rogue River-Siskiyou National Forest, the site is a nationally recognized historic state park. Self-guided tours of the inn are available Thursday through Sunday for those interested in tales of travelers along the Applegate Trail. Take a delightful meal at the on-site Wolf Creek Tavern — try the pulled pork sliders for lunch or buttermilk pancakes for breakfast if you plan to stay the night.

North Forty Beer Company

Roseburg for Art Lovers

Roseburg, on the Umpqua River, serves as a hub of culture and commerce for Douglas County. The midpoint between Grants Pass to the south and Eugene to the north — about 70 miles each way — you’ll find arts offerings like those of Umpqua Valley Arts, which features Northwest artists and a gift gallery filled with jewelry, wood sculptures and fiber art. Check out the city’s vibrant street-art scene on the Roseburg Mural Project self-guided tour of downtown. You can even stop by North Forty Beer Company for a pint at the same time — there you’ll find the massive mural “Rather Severe” by Portland artists Jon Stommel and Travis Czekalski, which features colorful renditions of both native and invented forest plants.

Top photo by Jak Wonderly