The town is 14 miles north of the CA border, just off I-5. Medford's airport is 13 miles away.
Things to see and do
$14-$20 — Tickets to a world-class play: For 75 years now, the Oregon Shakespeare Festival has dispelled the myth that high-quality theater comes at a high price. Although top tickets can run to $90, C-section seating ($20) is nothing to sneeze at. And with 11 plays (Cat on a Hot Tin Roof, Twelfth Night, and Hamlet, for starters) this summer on three stages, it’s okay to sacrifice a little quality for quantity. Don’t mind standing? The Elizabethan Stage—a Globe-inspired, under-the-stars pavilion that beats anything you’d find on Broadway—sells 20 ground-level SRO tickets daily (from $14) after all seats are gone.
$12 — Backstage passes: Okay, this isn’t exactly tossing back beers with Bono, but a two-hour behind-the-scenes tour led by a Shakespearean actor you might see in tights later is second best. Learn how the costumes develop from a sketch to final finery and how many props it takes to pull off a gunshot; then walk onstage and bow to a sea of empty seats. 10–11:45 Tue–Sun; 800/219-8161.
$0 — A courtyard show: Come to the grassy courtyard outside the Angus Bowmer Theatre an hour before curtain call for the totally free Green Show. Bring a picnic blanket and catch classical soloists or samba bands, actors performing a piece from a modern play, or a group of cellists playing Britney Spears. 7:15 p.m.; 15 S. Pioneer St.
$2-$10 — Live tunes: Ashland is home to some serious musical talent. While unknowns strum in the street, local pros on break from touring play in pubs; guitarist Jeff Pevar, reed man Michael Vannice, and singer-songwriter Frankie Hernandez are so worth a minor cover charge. Weekend afternoons, stroll along creekside Calle Guanajuato to hear live jazz, pop, or folk, and browse the crafts at the Lithia Artisans Market (lithiaartisansmarket.com).
$0 — A walk (and swim and show) in the park: Woodsy 93-acre Lithia Park sees its share of joggers and Frisbee throwers—but also ballet dancers, poets, and singers, who give both scheduled and spontaneous performances in the band shell. To beat the summer heat, cool your feet in the creek or take a dip in the reservoir. Winborn Way at Main St.; 541/488-5340.
$0 — An artsy First Friday: If you love wandering little galleries filled with contemporary regional art, then Ashland, home to more than three dozen, is your town. The best time to see ’em all is at the festive First Friday Art Walk (5–8), which stretches from downtown to A Street. Be sure to pop into the urban-hip Bohemia Gallery & Framing (closed Sun–Mon; 552 A St.; 541/488-5227) for live performance as inventive as the art. Download a gallery map at ashlandgalleries.com
Where to eat and drink
$9 — Breakfast by an Iron Chef: Neil Clooney, of Dragonfly Café and Gardens, has won top honors from Iron Chef Oregon. Dinner here is affordable (we love the $14 lettuce wraps of marinated steak and chicken with cucumber kimchi), but their made-from-scratch breakfast is our Dragonfly meal of choice. Blackberry pancakes ($7.50), an artichoke scramble ($9), jalapeño potatoes ($4.25)—enjoy them in the quiet tiered garden, illuminated by the morning sun. 241 Hargadine St.; 541/488-4855.
$15 — Ultra-local lunch: Good luck nabbing one of just 10 tables at the renowned New Sammy’s Cowboy Bistro for dinner. But the super-seasonal restaurant, run by disciples of Alice Waters, serves lunch too. It’s the same always-changing menu, created from organic pro-duce grown on the property or plucked from local farms—but at a set $15, it’s half the price of dinner. 2210 S. Pacific Hwy., Talent, 5 miles from Ashland; 541/535-2779.
$23 — Picnic dinner delivered: For an easy, pleasant, pre-theater meal, try an alfresco supper in Lithia Park. Sesame Asian Kitchen, across the street, will deliver an impressive picnic of crisp coconut calamari ($7.95), peppercorn-crusted seared ahi salad ($9.50), and banana-jackfruit spring rolls with vanilla-ginger ice cream ($5.95) directly to your patch of grass. From here, it’s a short stroll to the theater. 21 Winburn Way; 541/482-0119.
$3 — A seriously good slice of pizza: Another option for avoiding the long, drawn-out sit-down-dinner thing on theater night? Grab a slice of thin-crust from new Martolli’s Hand Tossed Pizza. 38 E. Main St.; 541/482-1918.
$0-$10 — Low-key wine tasting: Southern Oregon winemakers may be on the rise, but their intimate tasting rooms still pour free tastings of everything from Albariño to Zinfandel, paired with locally produced artisanal cheeses, breads, and chocolates. On a sunny summer afternoon, the three-tiered deck overlooking the vineyards at Weisinger’s (3150 Siskiyou Blvd.; 541/488-5989) is the place to be. The first taste is free; after that, it’s just $3 for three whites, $7 for six reds, or $8 for all nine tastings. If you’re looking for a full-on wine bar, Enoteca by EdenVale (17 N. Main St.; 541/482-3377) has views of the plaza and a killer selection of regional, daily-changing wines from which you can taste up to six reds or whites for $10, paired with light, pre-play bites (from $5).
Where to stay in Ashland
$179 — A Zen-like sleep: On the quiet end of A Street is Chozu Gardens, where a 1903 railroad rental cottage has been converted into two simple one-bedroom suites. Each has a fireplace and private garden, plus access to Chozu’s Japanese soaking baths (open to nonguests; closed Mon; $25 for 90 minutes). Go back and forth between the hot and cold pools, then unwind in the steam room and sauna before wandering into the tearoom for a cup of tea, sake, or sushi salad. Suites from $179; 832 A St.; chozugardens.com or 541/552-0202.
$175 — A hand-built retreat: Seven miles from Ashland in the Cascade foothills is ArtYCottage, an 850-square-foot home with a loft bedroom overlooking a full kitchen and sculptural wood furniture created by Tom Saydah, who lives next door. You could go into town or just stay home, hiking, reading, or—inspired?—writing. $175; two-night minimum; artycottage.com or 541/552-0858.