With its vegan cafés, hiking trails, science museum, and Tony-winning Shakespeare festival, Ashland, in southwestern Oregon, is an intriguing blend of hippie and brainy—very much like 17-year-old Shaina, an accomplished violinist and lifelong Ashland resident. Shaina has a 13-year-old brother, Kai; parents who run Brothers', a popular café on North Main Street; and a colorful assortment of friends (skateboarders, snowboarders, and fellow musicians). Things here, she says, are always interesting, thanks in part to the festival, which runs from February to October and draws 100,000 people to this hamlet of 20,000. The other big plus: the wilderness right in the town's backyard. Let Shaina be your guide.
WHERE THE ASHLANDERS ROAM "Everyone hangs out in Lithia Park [entrance at Water and N. Main Sts.], a block from downtown. It's gigantic: two duck ponds, a playground, meadows with lots of oaks, a reservoir for swimming, paths along Ashland Creek, and a Japanese garden (my favorite place to relax). The park is named for the mineral found in the drinking fountains here. Lithia is supposed to be good for you. Try it at your own risk; I think the water tastes gross and sulfury."
CATCH A SHOW "The Oregon Shakespeare Festival [15 Pioneer St.; 541/482-4331; www.orshakes.org] used to be only Shakespeare, performed on an open-air stage that looks like the Fortune Theatre in London. We now also have indoor theaters where contemporary plays are put on—this season there are eleven in all. I want to see Much Ado About Nothing (because it's not a heavy tragedy) and The Royal Family (should be funny). Arrive early to see the Green Shows—free music and dance performances that take place in the courtyard between the theaters. They're about a half-hour long, and all the locals come to watch."
GRAB A BITE "I'm in love with the orange-poppy seed scones and raspberry lemonade at my parents' place, Brothers' [95 N. Main St.; 541/482-6414], and the soy chai lattes at Rogue Valley Roasting Co. [917 E. Main St.; 541/488-5902]. For dinner, try Thai Pepper [84 N. Main St.; 541/482-8058; dinner for four $60]; I'm vegetarian, so I go for their tofu curries. If you want a burger and fries, head to Louie's Bar & Grill [41 N. Main St.; 541/482-9701; dinner for four $22], on the plaza."
NEED A ROOM? "When the Ashland Springs Hotel [212 E. Main St.; 888/795-4545; www.ashlandspringshotel.com; doubles from $139] was built, something like seventy-five years ago, it was the tallest building between Portland and San Francisco—even though it's only nine stories. It got fixed up a few years back and now has a spa and a restaurant called the Bulls-Eye Bistro [541/488-5558]. Look for my dad and his folk band Borderline there on a Friday or Saturday night."
HAVE AN ADVENTURE "It's so beautiful here that everyone's outdoorsy. Grizzly Peak hovers over Ashland and is visible all over town. It takes a few hours to hike to the top—don't worry, it's not that steep—and you get a view of the entire Rogue Valley. If you've never tried rafting before, this is the place to do it. You can take guided trips on the Rogue River with Noah's River Adventures [53 N. Main St.; 800/858-2811; www.noahsrafting.com; half-day trips $59]. Go to the Applegate River, a half-hour east of town, for an afternoon of swimming and sunning on huge rocks. You can walk up the river, then jump in and float down."
WHAT TO DO IF IT RAINS "Kids are crazy about the ScienceWorks Hands-On Museum [1500 E. Main St.; 541/482-6767], where you can launch bottle rockets or lift yourself up using a pulley. Bloomsbury Books [290 E. Main St.; 541/488-0029] is great for browsing and hanging out in the upstairs café. A few doors down, JeanneLouise Vintage Clothing & Costumes [296 E. Main St.; 541/488-0404] sells awesome stuff—my boyfriend got cool Western shirts there. You can try on a Romeo-ish doublet and breeches just for fun."
—AS TOLD TO EMILY HOLT