Ashland is a small town, home of the Oregon Shakespeare Festival , one of the largest and oldest regional theatres in the country. Southern Oregon University  balances the tourist population with students throughout the year. The weather is relatively mild, with a few days of snow in the winter, several days of 100F weather in the summer. Some believe that the town resembles 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 southeast along Main Street toward the library. This historic boutique shopping area is home to many amazing restaurants. In fact, you'll have a hard time finding a bad meal. Connected to this area is 93-acre Lithia Park  which was designed in part by John McLaren (also the designer of San Francisco's Golden Gate Park) in 1914. The other business district is around two miles to the southeast along Siskiyou Boulevard where it meets Ashland Street/Highway 66, near the Southern Oregon University campus and the Ashland Shopping Center. Ashland has a limited number of drive-through permits, and thus fast food joints. Wendy's, Taco Bell, Subway and other chains are still open in Ashland.
Outside of the business districts, Ashland offers a host of outdoor attractions. The famous Pacific Crest Trail , Crater Lake, rafting, biking and Mount Ashland  ski slopes are all nearby.
Many public places, including most hotels and B&Bs, coffeehouses and even pubs offer free wireless Internet access.
The Medford International Airport is located 15 miles north of Ashland and is serviced by United Airlines (San Francisco and Denver), Alaska Airlines/Horizon Air (Portland, Seattle, and Los Angeles), Delta Airlines (Salt Lake City), and Allegiant Air (Las Vegas and seasonal flights to Los Angeles and Phoenix/Mesa). Cascade Airport Shuttle (541) 488-1998, taxis and some hotels provides service from the airport to Ashland for a nominal fee.
If you are flying your own plane, you can use the Ashland airport (S03).
The closest Amtrak station is located in Klamath Falls, approximately 80 miles away. A shuttle meets the Coast Starlight from California at 10:20 a.m.each day arriving in Ashland at 1:00 p.m. If you are traveling from the north you must take the connection bus from Portland to the Ashland shuttle. Both shuttles arrive at Safeway about a half mile from downtown. Check www.amtrak.com for more information. *Note:* The Southwest Point shuttle from Klamath Falls to the area is much cheaper than adding the bus leg on an Amtrak ticket .
Parking is free, and easy to find in the wintertime, but summertime availability is a different story, with downtown parking getting quite scarce on evenings when the Shakespeare Festival has shows (i.e., every night but Monday). Many hotels and B&Bs are located close enough to the center of town to make it an easy walk. There are bike lanes downtown and extending outward from the downtown area, making this an easy town to bike around in.
The Rogue Valley Transportation District  route 10 runs a loop through Ashland every 20 minutes and continues to the transit center in Medford; these buses are $2 and run every 20 minutes during the day on weekdays. Be aware, however, the the buses run limited hours (5 a.m. to 9 p.m.), only run once an hour on Saturdays, and there is no service on Sundays.
Take a walk along Ashland Creek running down from the hills along Lithia Park, along Calle Guanajuato, running behind the Plaza restaurants and storefonts, 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. Do not bring dogs as they are forbidden in Lithia Park by municipal code with a stiff fine attached.
Ashland Creek and Winburn Way in Lithia Park
North Mountain Park, 620 N Mountain Ave, ☎ 541-488-6606, . The park has a nature center, demonstration gardens, playing fields, and several acres of wildlife-friendly open space and trails. Great place to take the kids.edit
Oregon Shakespeare Festival, 15 S. Pioneer Street, +1 541-482-4331, (email@example.com). February through November with 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 to 13 plays per season 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, with as many as nine different productions simultaneously in production. The staging and acting is of consistently high quality, and the festival is very popular and buying tickets in advance is highly recommended. 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"). If you come during the spring or fall and/or see shows on Tuesday, Wednesday or Sunday night you can sometimes get Rush tickets from the box office for 50% off. Call the box office the day of and ask if they think any shows will rush.
Ashland Independent Film Festival, held each year in April.
Rafting on the Rogue and Upper Klamath Rivers. Check out Noah's Rafting  for 1/2, one day, and multi-day trips - Indigo Creek Outfitters , Kokopelli River Guides , Momentum River Expeditions .
Emigrant Lake is a Jackson County park offering boating, lake swimming, fishing, and two large water slides. 
Crater Lake,  is the deepest lake in the US and known for its intensely blue waters. (80 miles north of Ashland).
Lithia Artisans' Market Downtown arts and crafts market, behind the Plaza on Calle Guanajuato, along Ashland Creek (seasonal, weather permitting).
First Friday Artwalk is a free event held the first Friday evening of every month in which the galleries and wineries join force. Patrons stroll Ashland's many galleries to meet the artists, see demonstrations and enjoy free refreshments and entertainment.
Britt Festival in nearby historic Jacksonville is an open-air concert space with varied musical events all summer.
Oregon Shakespeare Festival (Allen Elizabethan, Angus Bowmer and Thomas Theatres)
Oregon Cabaret,  is the other most compelling theatre in town. Enjoy dinner, drinks and hilarious musical comedy all in the same place. Even if you don't come early for dinner, order a slice of Dick Hay Pie for intermission.
The Green Show An eclectic mix of live performances prior to the performances in the Allen Elizabethan Theatre. 
Lithia Park’s band shell offers Ashland City Band  concerts on Thursday nights and Ballet Rogue performs on Monday nights during the summer. Dogs are allowed only on the closed/paved street that borders the band shell.
Ashland's status as a theater and tourist destination means more good restaurants per capita than might be expected in a town of its size. There are also plenty of budget offerings for the town's college students. Many restaurants offer vegetarian choices. Dogs are allowed at some restaurants that feature tables on sidewalks. Here are some popular places by price and area:
Big Al's burgers serves standard and specialty burgers and sandwiches (including veggie burgers) as well as a complete mexican menu.
The Breadboard - breakfast and lunch.
Bento's East Asian fusion lunch menu
Louie's $4.99 Recession Burger
Big Town Hero is a Northwest chain with sandwiches, soup, salad and snacks
Pita Pit is a fast food chain serving pita sandwiches
Cafe' Nomyen serves filled crêpes, both sweet (dessert) and savory (such as ham and cheese, turkey, tuna and veggie); the regular items are augmented with specials. Bubble tea, smoothies, and other specialty drinks, as well as ice cream, round out the menu.
Market of Choice Deli
Guiseppe's Pizza offers inexpensive slices
Fast food chains like Subway, Taco Bell and Wendy's
Noble Coffee Roasting.  Locally (small-batch) roasted organic and fair trade coffee and a sleek, laid-back space. 281 4th Street (541) 488-3288 noblecoffeeroasting.com Located in the railroad district near several art galleries and the Greenway walking/biking path. Free wireless.
Mix Sweet Shop. Serves Stumptown Coffee (from Portland -a leading direct trade coffee roaster). Right downtown on the plaza -high-quality sweets, pastries, and coffee. Homemade ice cream. Free wireless.
Evo's Coffee Lounge. Rich organic coffees&teas. Delicious brunch&snacks. Relax inside or out surrounded by paintings, sculptures, carvings.. Free wireless. 376 E. Main by the Library. 541-482-2261
Case Coffee. Located directly across from the SOU campus on Siskiyou Blvd. Free wireless. www.casecoffeeroasters.com
The Beanery. Ashland and Walker Streets, at the Southwest end. Free wireless.
Rogue Valley Roasting Company, 917 East Main Street. (541) 488-5902, Hours: Mon-Sat 6:45am-6:00pm, Sun 7am-3pm. Serving great coffee, fantastic locally-made pastries (both sweet and savory!) and ice cream, along with many other great hot and cold drinks. Free wireless, In-House Computer, as well as Outdoor porch or patio seating.
Hardware Café, A Street at Third. Mostly a bakery, has excellent stuffed bagels, breads and other baked treats. Not open on the weekend.
Bloomsbury Books has a coffeehouse in its second-floor loft. Free wireless.
Starbucks There are 3 Starbucks in Ashland. One is downtown next to the Chamber of Commerce, one is a stand alone building next to Southern Oregon University, and one is at the Albertson's at the south Ashland exit.
Ashland's Bed and Breakfast Network, (800) 944-0329,  is an association of 20+ inns that cooperatively provide free lodging referral service for visitors to Ashland, Oregon. ABBN is Ashland's only lodging association run entirely by volunteers, and the B&B have all met the associations high standards set for membership.
Chanticleer Inn, . Ashland's oldest luxury B&B in quiet historic neighborhood, strolling distance to downtown and theaters. Elegantly renovated 1920 Craftsman. Gourmet breakfasts, organic coffee, cookies, pvt baths, king beds, AC, WiFi, NYTimes, secluded gardens.
Winchester Inn, . Two blocks from OSF. 19 rooms and suites. Full gourmet breakfast included. Beautiful gardens. Free WiFi. Great packages available. Historic building, 1st southern Oregon Hospital. Reservations: 1-800-972-4991
Palm Cottages, . Across from Southern Oregon University, a few blocks from downtown, and is known for being a two-time winner of the Ashland Garden of Month award. It has a pool, a lot of gardens, phones, cable TV, kitchens, free WiFi and a horde of other amenities. Reservations: 1-800-691-2360
Columbia Hotel, . Right downtown 1 block from the Oregon Shakespeare Festival at 262 East Main Street. The Columbia is special in that walking up the stairs is akin to going back to 1910 when it was built. It's a must see when you visit Ashland. Toll-Free Line: 1-800-718-2530
The Ashland Hostel, . It is close to the downtown, at 150 N. Main, 541 482 9217. Rates run from $28 for dorm style digs to $79 for a family room. This is an old-fashion youth hostel with a 10am-5pm lock-out period (during which you can't be in your room) and separate male and female dorms. Just two blocks from the Plaza, The Ashland Hostel offers very reasonably priced accommodations in a home-like atmosphere (including kitchen privileges) for travelers of all ages, not just youths.
Arden Forest Inn, . Ashland's 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.
The Ashland Springs Hotel, . It is a historic building which was, for many years, the tallest building between San Francisco and Portland
The Plaza Inn, . Modern hotel located just north of the Plaza.
Ashland Commons, 437 Williamson Way (see website), ☎ 541-482-6753, . checkin: 4 p.m.; checkout: 10:30 a.m.. Two homey units; perfect for groups, families, as well as individuals. 2 equipped kitchens, 6 bedrooms, 4 baths, a/c, tv, wifi, off street parking, laundry, patio. Walk to downtown and theaters. $20-$45. edit
High Street Cottage, . Lovely little two-bedroom house within walking distance of downtown shops, theaters and park. Immaculately clean and well-kept by the owners.edit
Maxfield's, 635 Siskiyou Blvd. Ashland, OR, ☎ 541-941-6420, . Enjoy your stay at Maxfield's, a turn of the century vintage home in Ashland, Oregon. The house sleeps 2-8 and features a fully equipped kitchen, BBQ, televisions, DVD, CD stereo, WiFi, video and book libraries, laundry, central air conditioning, sauna and more. http://www.vrbo.com/302211edit
The Morical House Garden Inn, 668 North Main Street, . 9 room modern inn located on 2 acres of Master Gardens and lawns as featured in travel+leisure - award winning organic breakfasts "Intimacy, Luxury, Serenity"edit
This is a usable article. It has information for getting in as well as some complete entries for restaurants and hotels. An adventurous person could use this article, but please plunge forward and help it grow!