Toast the Bard with a local wine or a melted-chocolate drink in this artsy home of the Oregon Shakespearean Festival. Area code is 541, unless noted.
Oregon Shakespeare Festival 15 S. Pioneer St., (800) 219-8161, osfashland.org . Oregon Chocolate Festival March 7–9. Tastings, speakers, workshops, and chefs' demos. 212 E. Main St., (888) 795-4545, ashlandspringshotel.com . Ashland Independent Film Festival April 3–7. A cinematic marathon with screenings at the Varsity Theatre. 488-3823, ashlandfilm.org . A Taste of Ashland April 26 and 27. 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 Guided four-hour odysseys among the area’s 40-plus wineries and 140 vineyards (includes lunch). 482-9852, southernoregonwinetours.com . Or design a self-guided wine tour using a map of the region’s producers. sorwa.org .
Morning Glory Open seven days a week, this dining spot offers a breakfast menu with the usual suspects plus tempting dishes such as an Alaskan red crab omelet or a coconut almond waffle with lemon butter. For lunch, choose from a selection that includes a grilled lamb burger and an organic golden beet salad. 1149 Siskiyou Blvd., 488-8636, morninggloryrestaurant.com . 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 Stefan Pena’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 Ten unique suites overlook gardens and Ashland Creek. 70 Water St., 482-3315, ashlandcreekinn.com . Ashland Springs Hotel A nine-story 1925 tower with 75 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 and updated in February 2014. Some facts may have aged gracelessly. Please call ahead to verify information.