For the Oregon Shakespeare Festival's diamond jubilee, toast the Bard with a local wine or a melted-chocolate drink in this artsy town with urban tastes.
Oregon Shakespeare Festival 15 S. Pioneer St., (800) 219-8161, osfashland.org . Oregon Chocolate Festival Tastings, speakers, and workshops—next door to a year-round chocolate bar at Enchanted Florist. 212 E. Main St., (888) 795-4545, ashlandspringshotel.com . Ashland Independent Film Festival A Cinematic marathon with screenings at the Varsity Theatre. 488-3823, ashlandfilm.org . A Taste of Ashland Gourmet foodies present their delicacies in galleries around town. 488-8430, atasteofashland.com .
Enoteca by EdenVale A wine library that showcases southern Oregon offerings. 17 N. Main St., 482-3377, edenvalleyorchards.com . Liquid Assets More than 20 vintages by the glass in a classy wine bar and restaurant. 96 N. Main St., 482-9463, liquidassetswinebar.com . Southern Oregon Wine Tours $79 (includes lunch). Guided four-hour odysseys among the area’s 50-plus wineries and 140 vineyards. (888) 488-5075, ashland-tours.com. Or design a self-guided wine tour using a map of the region’s producers. sorwa.org .
American Trails Native crafts and whim-sically painted Oaxacan animal figurines. 27 N. Main St., 488-2731, americantrails.com . Out of the Blue An eclectic gallery bursting with beads, baubles, and exotica from around the world. 101 E. Main St., 482-6416.
New Sammy’s Cowboy Bistro The renowned little restaurant halfway between Ashland and Talent has doubled its capacity and kept its quality. 2210 S. Pacific Hwy., 535-2779. The Peerless Restaurant & Bar Perfection is a garden table and chef Mark Carter’s affordable small plates. 265 Fourth St., 488-6067, peerlessrestaurant.com . Standing Stone Brewing Company A former auto garage turned high-tech brewpub and eatery. 101 Oak St., 482-2448, standingstonebrewing.com .
Ashland Creek Inn From $135. Ten unique suites overlook gardens and Ashland Creek. 70 Water St., 482-3315, ashlandcreekinn.com . Ashland Springs Hotel From $125 for AAA members. A nine-story 1925 tower with 100 luxurious rooms. 212 E. Main St., (888) 795-4545, ashlandspringshotel.com .
Request the Oregon & Washington TourBook and map at AAA.com  or any AAA branch office. To learn more about area attractions or to get a winery map, contact the Ashland Chamber of Commerce: 110 E. Main St., 482-3486, ashlandchamber.com .
Photography by Robbie McClaren 
This article was first published in March 2010. Some facts may have aged gracelessly. Please call ahead to verify information.