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6 Ways to Explore Ashland

by Laura O. Foster

1. Hit the trail

Explore Lithia Park, where downtown transitions into one of Oregon’s great public spaces. Hike along Ashland Creek; visit the Japanese garden, rose garden and duck ponds; go birding or splash in the swimming reservoir at the park’s far end. See the Lithia Park Trail Guide to find the adventure that best suits you. From the park, connect to the 15,000-acre Ashland Creek Watershed, where trails wind along creeks, through oak woodlands and up the slopes of Mt. Ashland. Download or order a free map of city streets and the watershed’s trails.

Cascade Siskiyou Scenic Bikeway

2. Explore on two wheels

In this famously bicycle-friendly city, it’s easy to experience Ashland’s varied terrain with your own pedal power. In July, ride the annual Up and Down Ashland cycle event. From spring to fall, experienced riders can get their workout with a side of scenery along the challenging, 55-mile Cascade Siskiyou Scenic Bikeway, which starts and ends in Ashland. For family road riding, Ashland is a top cycle-friendly city, with urban bike routes, parks and historic neighborhoods to explore. From the Ashland Dog Park, hop on the paved Bear Creek Greenway (free from motorized vehicles) and enjoy miles of biking adventure.  Mountain bike and gravel riders can use a free map to find a single-track whoop-de-doo from the top of Mt. Ashland, or an invigorating cruise on gravel roads. Rent bikes or hire a local guide to tailor a route for you.

Caldera Brewing by Brown W. Cannon III

3. Enjoy the ales

Raise a glass in Ashland to history. At Caldera Tap Houseoverlooking Ashland Creek, sample 20 beers on tap as well as housemade sodas or visit their restaurant and brewery, just off exit 14 on Interstate-5. Whet your palate with a light ginger beer, or settle in for the night with the bourbon barrel-aged Old Growth Imperial Stout, which counts as dessert too. At Standing Stone Brewing, a renovated auto body shop downtown, the kids will love watching the wood-fired pizzas get fired up in the open kitchen. Dishes like lamb burgers and Oregon pear salad pair well with a refreshing Southern Sun Rye or Pomegranite Wheat.

4. Fuel up with farm-to-table food

Ashland is all about fresh, seasonal and sustainably prepared food, so beware — it may be hard to pick just one spot. From breakfast to late-night cocktails, Brickroom features small, shareable plates prepared by Chef Skye Elder, one of many local chefs and mixologists awarded top honors at the Ashland Culinary Festival, the four-day celebration each November of Southern Oregon’s edible riches.

Smithfields Restaurant and Bar is all about locally sourced and inventively prepared meat. At MÄS, daily-changing dinners are served omakase-style — chef’s choice; each meal depends on the market bounty that day. At Larks Restaurant at the Ashland Springs Hotel, wake up to a spring benedict for brunch or linger over a house-brined Carlton Farms pork porterhouse for dinner, which pairs beautifully with a local pinot. 

For happy hour, wander the gardens at Hearsay with a jade rose — a huckleberry-infused vodka with basil simple syrup, lemon, a dash of angostura bitters and layer of foamy egg white. The restaurant’s cozy ambience in an old church is the perfect place to cap a day outdoors. At the 1970s-retro Luna Cafe and Mercantile — a local farm-to-table favorite — kick back on the pet-friendly patio or the deck overlooking the hills with a spiced toddy or rustic Manhattan.

Save room for something sweet: Branson’s Chocolates is one of several handmade confectioners in Ashland that invite visitors to pop in for samples. The Oregon Chocolate Festival each March also pairs well with Ashland’s outdoor adventures, including the festival’s Charlie’s Chocolate 5K Run/Walk.

Weisinger Family Winery

5. Sip award-winning wine

Savor the tempranillo, viognier and other diverse varieties that thrive in the Rogue Valley — Oregon’s warmest and driest and most diverse wine-growing region, with a climate like Bordeaux, France. Hire a guide to handle the driving, and travel the Bear Creek Wine Trail. Its passport gives you three free tastes at 12 wineries.

On the Trail, Weisinger Family Wineryspecializes in limited production wines from local vineyards. Sit by the fire pit at Dana Campbell Vineyards. Channel the ancient Romans in the Pavilion Tasting Room at Belle Fiore Winery, or have a private wine tasting in its spectacular chateau. On 40 acres, Grizzly Peak Winery offers tastings with views of Mt. Ashland and Grizzly Peak. At Eliana Wines bring snacks, and picnic among the vines. About 15 minutes from downtown, Irvine & Roberts Vineyards is one of Ashland’s newest tasting rooms, with stunning views of their estate vineyards and surrounding hillsides. In town, Hither Coffee and Goods specializes in natural and biodynamic wines.

Chozu Bath & Tea Gardens by Jared Cruce

6. Indulge in a spa day

When it’s time to recharge, Ashland is ready for you. Book your stay at Lithia Springs Resort and enjoy an unforgettable wellness getaway. Surrounded by beautifully manicured gardens, the resort offers soaks in curative waters piped into each guest room, an outdoor pool, fitness room and an onsite spa. Step into tranquility at Chozu Bath & Tea Gardens. Soak, steam and plunge (into a cold pool) in the classic Japanese bathhouse tradition. At Waterstone Spa, downtown or at Lithia Springs Resort, give your body its own vacation with a massage or foot treatment. On Ashland Creek, the Blue Giraffe Day Spa & Salon offers a calm yin to the active yang of your Ashland getaway with soaks, steams and massages.

When you go: Find yourself surrounded by history at the Ashland Springs Hotel, a 1925 downtown landmark. The hotel includes 70 guest rooms, Larks Restaurant, an English garden and city views. A short drive from downtown, enjoy the hip, retro-modern design of Ashland Hills Hotel & Suites, a 14-acre property featuring two tennis courts, an outdoor pool and jacuzzi, the casual Luna Cafe and Mercantile, rental bikes and other family amenities. For a B&B or boutique inn experience, visit Stay Ashland. Ashland’s visitor resource, Travel Ashland corrals the many options into one site.