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 southwest along Main Street toward the library. This old-fashion 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 southwest 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 slope are all nearby.
Many public places, including most hotels and B&Bs, coffeehouses and even pubs offer free wireless Internet access.
Exit 11 (Northbound only), 14 or 19 from Interstate 5 in Oregon. Note that in Oregon it is illegal to pump your own gas.
Greyhound  stops in nearby Medford. The local RVTD bus Route 10 stops at Mr. C's (where the Greyhound bus stations is) at :26 & 56 past the hour. The bus ride into downtown will take you about 10 minutes. Buses run between 5:26am and 6:56pm, Monday-Friday. You pay when you get on the bus.
Taxi service is available from Ashland Taxi Cab (541) 890-8080 or Yellow Cab (541) 482-3065.
The Medford International Airport is located 15 miles north of Ashland and is serviced by United Air Lines, and Alaska Airlines/Horizon Air. 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 tickety 
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.
Most days, the Rogue Valley Transportation District  operates buses running from one end of town to the other; these buses are $0.50 for riders remaining within Ashland ($2 for those going outside the city limits). Be aware, however, the the buses run limited hours (5:30 a.m. to 7 p.m.) and do not run at all on weekends.
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.
Ashland Creek and Winburn Way in Lithia Park
Oregon Shakespeare Festival, 15 S. Pioneer Street, +1 541-482-4331, (firstname.lastname@example.org). 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 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"). 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 or as little as $6. Call the box office the day of and ask if they think any shows will rush. Also $30-50 (discount during spring and fall, 25-50% discount for youth and seniors).
Ashland Independent Film Festival, held each year in April.
Rafting on the Rogue and Upper Klamath Rivers. Check out Momentum River Expeditions , Noahs Rafting , The Adventure Center  for 1/2, one day, and multi-day trips.
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).
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 events all summer.
The Fourth of July Parade is a big event for the town; it draws visitors from around the region.
Festival of Lights Parade at the end of November; when all the Christmas lights in the town are turned on.
Oregon Shakespeare Festival (Elizabethan, Angus L. Bowmer and New Theaters)
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.
Lithia Park’s band shell offers Ashland City Band  concerts on Thursday nights and Ballet Rogue performs on Monday nights during the summer.
Ashland Street Cinema (First-run movies--located in the Ashland Shopping Center at southwest end of town)
Varsity Theater (Some smaller run and independent films--located downtown near Ashland Springs Hotel)
Bliss Out Biscotti (The Pacific Northwest's only All-organic biscotti baking company).
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. Here are some popular places by price and area:
The Breadboard - breakfast and lunch.
'Bento's' East Asian fusion lunch menu .
Louie's sometimes has inexpensive lunch specials
Big Town Hero is a Northwest chain with sandwiches, soup, salad and snacks
Market of Choice Deli
Fast food chains like Subway, Taco Bell and Wendy's
Guiseppe's Pizza offers inexpensive slices
Artik Creamery - Locally handcrafted organic ice cream, some of the best anywhere. Saturdays at Ashland Growers Market across from Post Office on Lithia Way 9am-1pm & Tuesday Growers Market at Ashland Armory on East Main & Wightman St. 8:30am-1:30pm 
The Black Sheep - Remarkably authentic English pub grub.
Brothers Deli - Breakfast and lunch only; omelettes, burgers, and sandwiches.
Gepetto's - Hot entrees, baked potatoes, etc. (well-behaved dogs OK at sidewalk tables.)
Greenleaf Restaurant - Fresh, Healthy & Delicious. Family Friendly. Breakfast, Lunch, Dinner. Catering, Picnics, Boxed lunches. Vegetarian, Gluten Free & Vegan options. Hot sandwiches, soups, salads and specialties. Creekside dining.A local favorite for over 25 years.
Louie's Bar and Grill Voted "Most Interesting Burgers" and "Best Value on the Plaza" by Ashland's Sneak Preview Magazine. A fun and family-friendly "Cheers" atmosphere. Creekside dining.
Munchie's - Burgers, burritos, and amazingly generous pies and cakes.
Pangea - Wraps, sandwiches, salads and soups. (well-behaved dogs OK at sidewalk tables.)
Grilla Bites - Lunch and Dinner. Organic salad bar, grilled sandwiches, vegetarian options. Creekside Dining.
Apple Cellar Bakery - Breakfast and lunch; breads, pastries, pies and cakes 
Morning Glory Restaurant, . - Wonderful breakfasts and lunches. 1149 Siskiyou Blvd., right next door to Subway.
Omar's - Traditional dining, steaks & seafood.
Wiley's Pasta World - Homemade organic pastas.
Standing Stone Brewery - Listed as a brewery, is a fine restaurant too.
Amuse - Fine cuisine and extensive wine selection. , 541-488-9000.
Chateaulin - French bistro, longtime favorite. , 541-482-2264.
Dragonfly Cafe and Gardens, . - Latin-Asian Fusion Cuisine, Breakfast, Lunch, Dinner, and Drinks. "Be Curious"
Larks - American gourmet, including comfort foods. (well-behaved dogs OK at sidewalk tables.)
Pasta Piatti - Italian cuisine and extensive wine selection. (well-behaved dogs OK at sidewalk tables.)
Thai Pepper - Thai cuisine. Creekside dining.
The Winchester Inn - Cosmopolitan cuisine. Wine Spectator Award of Excellence. Great wine bar. , 541-488-1113
Lela's Café, 541-482-1702. - Creative Northwestern. (well-behaved dogs OK at sidewalk tables.)
New Sammy's Cowboy Bistro, 541-535-2779.- Fresh gourmet. Actually slightly north of Ashland in Talent.
The Ashland Creek Bar and Grill Newly reopened with a satisfying selection of beer and pizza.
Standing Stone A microbrewery with several beers and a 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.
Louie's Bar and Grill Family-friendly "Cheers" atmosphere, bi-weekly rotating microbrews, historic 100-year-old restored bar.
The Caldera Taproom Extensive offering of beer brewed in Ashland by Caldera Brewing Company with a small menu of pub fare.
Alyson's of Ashland has a great selection and very knowledgeable staff. They also feature a gourmet deli with a great lunch menu and a gourmet cookware shop.
Liquid Assets is a great place to relax and try different local wines. They also often feature local musicians in their cozy space.
Winchester Wine Bar specializes in local wines. They have wineries pour every Thursday and Friday night. Live music on Friday, Saturday and Sundays with no cover.
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.
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.
Key of C Coffee House and Bakery, 116 Lithia Way, (541) 488-0302, Hours: Monday-Saturday 6am-4pm, Sunday 7am-3pm. Serving Intelligentsia Coffee, seasonally-sourced Direct Trade coffee. Free and very strong wireless. Known in town for their friendly staff and their very popular NY style handmade bagels. Each bagel is made by hand the morning of and comes in a vast array of unique flavors. Open every day with a mellow atmosphere; perfect for students, travelers, and locals alike. Sunday mornings are always packed with dancers, musicians, and world music enthusiasts for the free Eastern European folk music from 7am -11am.
Bloomsbury Books has a coffeehouse in its second-floor loft. Free wireless.
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. Rates are $140-190 in winter, $165-299 in spring/fall and $205-299 in summer. 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. Rates range from $64 to $98 in winter, $69-$115 in Spring/Fall and $95-169 in summer. Reservations: 1-800-691-2360
Columbia Hotel, . Right downtown 1 block from the Oregon Shakespeare Festival at 262 East Main Street. Rates range from $49 to $69 in winter, $59-$105 in Spring/Fall and $73-$125 in summer. 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
Ashland's Bed and Breakfast Network, (800) 944-0329,  is an association of 25+ 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.
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 $89 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, . A hotel known for its small rooms and high prices located downtown on East Main Street. It is a historic building which was, for many years, the tallest building between San Francisco and Portland
The Plaza Inn, . Generic hotel located north of downtown.
Mt Ashland House The only year round vacation rental actually on Mt. Ashland. Located on the access road (Mt. Ashland Ski Rd) is a 2 bedroom, split level log home, minutes from skiing (Mt. Ashland Ski resort), hiking (The Pacific Crest trail), biking and the Beautiful Tashi Chöling’s traditional Tibetan temple, makes this the perfect vacation rental. Mt. Ashland House is on a acre of land, in a private, secluded location. Mt. Ashland House is just 6 miles north of the California border, at the 5,000 foot level is private owned by Craig Dillen, who purchased the home in 1989, with the expressed intent of turnign it into the vacation rental it is today.
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.
Historic Rental in Railroad District, ☎ 541-482-1289, . checkin: 3PM; checkout: 10:30AM. Lovely apartment within the RL Carey house built in 1880. 7 blocks from downtown Ashland. 2 bedrooms, one bath with large hot tub and nice yard. Air conditioning, ceiling fans, extra-deep bathtub, BBQ, side brick patio and back deck make this a perfect retreat. High speed wireless internet and premium cable TV package.$800/week.
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.
Ashland Mountain House B&B, 1148 Old Hwy 99 south (4 miles south of town), ☎ (866)899-2744, . checkin: 4-7PM; checkout: Noon. First a gold rush inn, then a stagecoach stop, the Ashland Mountain House is now a B&B.$135-$199. (42:07:34N,122:36:37W)
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