Scenic Southern Oregon is home to some of the most varied and colorful terrain in the state, from towering mountain peaks to verdant valleys. The region’s largest communities — Grants Pass, Medford and Ashland — are in or adjacent to the fertile Rogue Valley, which is famous for its abundance of berry and produce farms, orchards and vineyards. The latter are responsible for the region’s emergence into one of the state’s leading winemaking destinations. In and around these communities, many art galleries, indie boutiques, craft breweries and coffeehouses, and locavore-oriented restaurants thrive. Medford is also one of the main gateways to the fifth-oldest national park in the nation, Crater Lake National Park, which is anchored by the ninth-deepest lake on the planet.
Day One: Grants Pass and the Rogue River
After arriving at Rogue Valley International-Medford Airport, make the 40-minute drive west on I-5 to the inviting town of Grants Pass, which is the starting point for adrenaline-producing white-water rafting and jet-boat trips along the Rogue River, a nationally designated Wild and Scenic River that courses through some of Southern Oregon’s most dramatic scenery. Some outfitters in Grants Pass also offer more relaxed float adventures along the Rogue, including one that provides participants with a chance to sample craft beer while they enjoy the river breezes and passing scenery. The Paddled Pub excursions depart at noon and 3:45 p.m. from popular Climate City Brewing Company in downtown Grants Pass. You purchase draft beer in growlers before you set off, then drink up at your leisure (snacks are provided, too) as you float down the Rogue.
Spend the night in Grants Pass or Medford.
Day Two: Crater Lake and Rogue Valley Wine Country
From Medford it’s just under a two-hour drive northeast to reach spectacular Crater Lake National Park, the deepest body of water in the United States. This crystal-clear, sapphire-blue lake has formed inside the caldera of Mt. Mazama, a volcano that exploded in spectacular fashion some 7,700 years ago. Make the 33-mile auto tour around Rim Drive, where you’ll encounter numerous scenic viewpoints that offer awesome photo opportunities. Take a scenic narrated cruise around the lake with a stop at Wizard Island (a volcanic cinder cone), and have lunch at the grand 1915 Crater Lake Lodge. The restaurant overlooks the lake and has a terrace with majestic water and mountain views, and the kitchen specializes in locally sourced Northwest fare, including a blackberry-marionberry-raspberry cobbler that’s justly famous.
Following lunch, return to explore the Rogue Valley wine region, which has earned a sterling reputation among oenophiles for its more than 150 wineries specializing in everything from Bordeaux-style wines (cabernet sauvignon, merlot) to tempranillo, syrah, sangiovese, viognier and a slew of other old-world grapes. Just north of Medford in the small town of Central Point, Ledger David Cellars Tasting Room is an excellent option for sampling award-winning cabernet franc and chenin blanc. Next door you can try some of the finest blue cheese in America at Rogue Creamery; the heady Smokey Blue is a favorite for pairing with Oregon berries or charcuterie, or you can simply enjoy it by itself with crackers (Rogue sells gourmet picnic supplies, too). It’s just a short stroll to Lillie Belle Farms Handmade Chocolates, whose talented chocolatiers handcraft each and every organic sweet. The mouthwatering options include lavender sea-salt caramels, Oregon-hazelnut chocolate bars and distinctive blue-cheese truffles made with cheese from Rogue Creamery.
Day Three: Ashland
Upon checking out of your hotel in Medford, make the 20-minute drive south to the outdoorsy and creative college town of Ashland, which is famous for its annual Oregon Shakespeare Festival (performances run from mid-February through October). The city’s charming, tree-shaded downtown also abounds with distinctive shops and culinary destinations, from organic cafes to sophisticated farm-to-table restaurants. Start your stroll around town by fueling up with a single-origin, handcrafted Americano or cold-brew iced coffee from Noble Coffee Roasting, which sources its fair-trade beans from small farms in Colombia, Ethiopia, Bali and other coffee meccas, roasting beans daily on premises. If it’s a nice day, sip your coffee while sauntering through downtown’s leafy Lithia Park, a verdant 93-acre patch of lawns, gardens, duck ponds and forestland featuring a gurgling creek fed by mineral springs.
Over a three-day weekend in early March, the Oregon Chocolate Festival takes place at the inviting Ashland Hills Hotel & Suites and features the distinctive and delicious products of more than 30 artisan chocolatiers from throughout the nation, including several Oregon-based companies. You can view dramatic chocolate sculptures, stroll a chocolate-themed downtown art walk, feast at a special chocolate maker’s dinner, attend a variety of workshops and chef demos, and, of course, sample dozens of amazing chocolate bars, candies and confections.
Ashland’s reputation as a mountain biking destination is also gaining momentum, with a web of world-class trails that appeal to a range of skill levels. Spring Thaw Mountain Bike Festival, the state’s largest and oldest mountain bike event, is held in Ashland every May.
Day Four: Depart for Medford
It’s a short drive from Ashland to the airport in Medford, but don’t be surprised if you can’t make yourself leave this leafy wonderland. Jacksonville, a charming old gold rush town, is on the way back and worth visiting.