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Ashland, Oregon may be a small town but it can rival big cities with theater, outdoor activities, wine and farm-to-table food.

Photo: Queen Elizabeth in the performance of Shakespeare in Love. Photo Credit: Jenny Graham

Recently my husband and I drove 6 hours from San Francisco to indulge our passion for theater. We bought tickets for Julies Cesar, Shakespeare in Love and a Backstage Tour. The acting, sets, costumes and imaginative productions left us wanting to see more. So Monday when the theaters were closed, we spent the evening at a musical Cabaret Show tapping our toes and singing along to show tunes, jazz, blues, and bebop. 

Every morning we walked in the town’s 93-acre Lithia Park through the pink blossoms of Rhododendron and Dogwood trees.

Move over Shakespeare. Wine tasting tours have taken center stage for many visitors.

In 2016 the Wine Enthusiast rated Ashland among the Top 10 Best Wine Travel Destinations in the World. Take your pick of over 120 wineries clustered around Ashland and discover delicious Oregon Pinot Noirs.

One afternoon we drove 30 minutes north of town through farmland, pear orchards and forested hills to the award-winning DANCIN Vineyards. It is located a mile outside of Jacksonville, an Old West town founded after the Gold Rush in the 1850’s, and now designated a National Historic District.

Welcome to Tuscany in Southern Oregon at DANCIN Vineyards.

The owners, Dan Marca, and his wife Cindy personally welcome guests. “We offer great food to go with the wine experience,” Dan told us. “Unlike many wineries, DANCIN is open until 8:00 PM May through September, so our visitors can taste wine and dine al fresco.” he added. The menu offers wood-fired flatbread, cheeses, antipasti, salads, artisan pizzas and desserts. Cindy brought us homemade sausage-stuffed mushrooms and we clinked our glasses of 2014 Spetette Pinot Noir toasting the setting sun.

With the sun beating down and snow-capped Mount McLoughlin rising above, we drove into the gates of the winery and immediately felt transported to Tuscany. The tasting room was in an elegant vine-covered, amber stone building. Visitors sat and sipped in the spacious gardens near a fire bar while a chicken pecked around the picnic table under a graceful black walnut tree.

Enjoy the views at Weisinger Family Vineyards.

The next day we drove 10 minutes south of Ashland to sample Chardonnays, Malbec and Pinto Noir at Weisinger Family Winery. Eric, the winemaker and son of the founder, poured wine at the tasting bar. Eric has done everything from planting and picking grapes, to blending wines, in France, California, New Zealand and Australia.

Sample award- winning Chardonnays, Malbec and Pinto Noir at Weisinger Family Winery.

“We are not a mass production winery,” Eric explained. “We sell 98% of the wines right here. Wine is our passion,” he added. “You have to love it because you wouldn’t work this hard for anything else. Terroir is the fingerprint of the vineyard,” he added. “We have one of the most diverse geological regions in the country and the same latitude as France, Spain and Italy. Plus we have a 7-month growing season.” We lingered for an hour sipping wine, sampling a cheese platter, and taking in the views of the sun-drenched vineyards.

Where to Dine

The town’s culinary boom attracts young experimental chefs creating unique dishes. One of the new stars in town is award-winning Chef Josh Dorcak, 2017 Iron Chef Oregon and two-time Ashland Culinary Festival Top Chef. Chef Dorcak opened a pop up style small plate restaurant, Más. 

Josh excels at the farm-to-table dining experience. “You’ll never see a can opener here,” he boasts.  

The French cuisine is outstanding at Amuse and Alchemy Restaurant offers top-notch gourmet dining in a garden setting or inside.

Where to Stay

We opted for a European-style hotel – with free parking – so we could walk to the Shakespeare Festival, restaurants, shopping and . Ashland’s bed and breakfasts are well known for their charm and service. Other accommodations range from well-known hotels to lodges, cabins, and inns.

Text and unmarked photos by Marybeth Bond