Ashland is at the south end of the Rogue Valley, only about 15 miles from the California border, on one of the two north/south routes through Oregon.

Ashland is a college town, home of Southern Oregon University, but it's mainly known for its live theater, particularly the Oregon Shakespeare Festival . The weather is relatively mild, a few days of snow in the winter, several days of 100F weather in the summer. You'll swear you were somewhere in northern Italy or Switzerland, with snow covered peaks in the winter, a lake not too far away in the valley, and a nice, small-town, community feel that is oh-so-rare these days in the States.

There are two main business districts: one downtown, centered on the Plaza and running southwest along Main Street toward the library. Many restaurants and opportunities for shopping are clustered in this area. The other is around two miles to the southwest along Siskiyou Boulevard where it meets Ashland Street/Highway 66, near the Southern Oregon University campus and the Ashland Shopping Center.

Many public places, including most hotels and B&Bs, coffeehouses and even pubs offer free wireless Internet access.

Activities

 • Oregon Shakespeare Festival, 15 S. Pioneer Street, +1 541-482-4331. February through November, no plays on Mondays. One of the largest venues for production of Shakespeare's plays in North America, OSF provides a continuous run of theatrical works from early spring until late fall. In a single weekend, adventurous theater lovers can easily fit in 3 or 4 plays. The rotating repertory season of 11 plays typically includes three Shakespeare pieces, with the remainder made up of modern classics, contemporary pieces, and often one or two world or West coast premieres. The staging and acting is of consistently high quality, but the festival is very popular and buying tickets in advance is almost mandatory. Last-minute travelers can pick up spare tickets at the on-site box office or by holding up a sign on the festival plaza (aka "the bricks"). $30-50 (discount during spring and fall, 25-50% discount for youth and seniors).

Attractions

Take a walk along Ashland Creek running down from the hills along Lithia Park, along Calle Guanajuato, running behind the Plaza restaurants and storefronts, and through the center of town. There are plenty of picnic benches and sitting benches for contemplation and conversation in the woods, as well as duck ponds, playgrounds, two large greens and a skating rink in the winter.

Dining

Most dining in Ashland is not inexpensive, but is generally of very good quality--you will probably not go wrong. Most places have many vegetarian choices. Here's a stab at some places by price and area:

Budget
 • Bento's (Asian fusion lunch menu)
 • Railroad district
 • Hardware Cafe A Street at Third (Breakfast--huge stuffed bagels for $1.50 and eggs and toast for $3.00)
 • Cozmic Pizza: A Street Marketplace (Organic pizza, including many vegetarian toppings)
 • La Familia: A Street Marketplace (Mexican)
 • Market of Choice deli
 • Morning Glory Restaurant 1149 siskiyou blvd, right next door to subway

Mid-range
 • Pangea (wraps, sandwiches, salads and soups)
 • Ashland Bakery Cafe (breakfast and lunch; breads, cakes and other goods)
 • Greenleaf Cafe (Hot sandwiches, soups, salads and specialties)
 • Gepetto's (hot entrees, baked potatoes, etc.)
 • The Black Sheep (remarkably authentic English pub grub)
 • Munchie's (burgers, burritos, and amazingly generous pies and cakes)
 • Brothers Deli (breakfast and lunch only, omelet's, burgers, and sandwiches)
 • Wiley's Pasta World

Splurge
 • Pasta Piatti (Italian cuisine and extensive wine selection)
 • Thai Pepper (Thai cuisine)
 • Monet (French provincial)
 • Chateaulin (French bistro)
 • Lela's Cafe (Creative Northwestern)
 • Omar's (traditional fine dining)

Drink

Brewpubs
 • The Ashland Creek Bar and Grill
 • Standing Stone (microbrewery with several beers and full menu)
 • The Black Sheep (English-style pub offering a full menu of many pub food classics and specialties as well as draft and bottled beers and spirits.)

Local Wines
 • Alyson's of Ashland (great selection, very knowledgeable staff)

Coffeeshops
 • The Beanery: Ashland and Walker Streets - Southwest end.
 • Rogue Valley Roasting Company: East Main and Eighth Streets. Free wireless.
 • Hardware Cafe A Street at Third. Mostly a bakery, has excellent stuffed bagels, breads and other baked treats. Not open on the weekend.
 • Key of C Coffee House and Bakery: 116 Lithia Way, (541) 488-0302, Hours: Monday-Saturday 6am-4pm, Sunday 7am-3pm. Free wireless.
 • Bloomsbury Books has a coffeehouse in its second-floor loft. Free wireless.

Public Drinking Fountains
 • A fountain of "Lithia Water" can be found in Lithia Park. The taste is... memorable.

Lodging

 • There is a youth hostel very close to the downtown, at 150 N. Main, 541 482 9217, with a website at http://www.ashlandhostel.com. Rates run from $20 for dorm style digs to $50 for a family room.
 • Arden Forest Inn, Ashland Oregon's Premier Lodging Destination for Theatre Enthusiasts. This unique Ashland bed & breakfast is situated on an acre of lush, park-like gardens and offers over 15 years of hospitality excellence. Arden Forest Inn has maintained the top rating for Ashland on TripAdvisor since 2000.
 • The Ashland Springs Hotel is a luxury hotel located downtown on East Main Street. It is a historic building which was, for many years, the tallest building between San Francisco and Portland.

Many good bed-and-breakfast inns can be found through these sites:
 • Ashland B&B Clearinghouse
 • Ashland Bed and Breakfast Network
 • BedAndBreakfast.Com 
 • Oregon Shakespeare Festival Accommodations page