Ashland offers the best shopping in the area, with clothing boutiques, bookstores, and much more lining the downtown area. Ashland is also a top-rated art town, with more than 20 art galleries that typically stay open late on the first Friday of each month. You can see innovative artwork in wood at the Ashland Hardwood Gallery on Main Street. And The Web-sters, a knitting and weaving store also on Main Street, offers impressive sweaters, jackets, and other accessories. Contemporary art sets the scene at the Hanson Howard Gallery on North Main Street, and Davis & Cline on A Street in the Railroad District. And while you’re in that neighborhood, stop by the Gathering Glass to watch glass being handblown.

On your way from the Railroad District to downtown Ashland you can't miss a cute little maternity and baby store on Lithia Way called Bump. It's the only store that you can shop for mom and the baby. They gift wrap for free and all of their things are available online at bumpashland.com. From there it's off to Yogert Hut!

Ashland is also big on book stores, so head to East Main Street to check out Bloomsbury Books and Soundpeace, or North Main Street for Tree House Books. Used books are also available at Bookwagon on Ashland Street .

Every weekend from May through October you can visit the Lithia Artisans Market, located on Calle Guanajuato behind the Plaza, across the street from Lithia Park . Open from 10am to 6pm on Saturdays, and from 11am to 5pm on Sundays, the various stalls and booths offer all kinds handcrafted jewelry, handstitched dresses, original hats and caps, unique toys, patchwork quilts, fine art paintings, sculpted pottery, and much more. Ongoing entertainment includes jugglers, puppeteers, and live jazz, blues, and folk music.

For a more mundane shopping experience, you can head to the Rogue Valley Mall in nearby Medford . The two-level mall has more than 100 retail stores, a food court, and three department stores, including JC Penney. Medford also has a Walmart Supercenter, Sportman's Warehouse and a Costco, all located east of town on or just off Crater Lake Highway.