Ashland, Oregon

Gateway to Rogue Wine Region, Crater Lake National Park, Wild Rivers Coast and Epic Oregon Backcountry

The Oregon Shakespeare Festival

The festival opens in mid-February and runs continuously for nearly 9 months. OSF mounts both classic and contemporary plays in repertory, all of them world-class productions. PBS dubbed OSF "a major force in American theater". Other wonderful things to do and see in the Spring include...

aiff-2013-al_case-the-moo-manPhoto by Al Case, Ashland Daily Photo 

Ashland Independent Film Festival

More than 70 filmmakers and their films from all over the world decend on Ashland in early April for an intense 5-day festival. All films are viewed in Ashland's historic Varsity theater or Armory. After each showing, the filmmakers share with the audience their creative process. B&Bs support the event by providing housing for many of the filmmakers

561e8d2ca0d5e62b34000036_MainGallery7Photo: Schneider Museum of Art, Southern Oregon University

Ashland Galleries

Taste of Ashland - Each April, the Ashland Gallery Association sponsors a festival of wine, food and art. Ticket holders wander through the galleries tasting food from the local restaurants and sipping wine from local vineyards.

Art Walk - On the first Friday of each month from 5:00pm to 8:00pm association’s gallery members host a series of “open houses", offering visitors a chance to view art, listen to music, and nibble on tasty treats.

Adventure & Nature

The Ashland Ski Resort offers challenging and uncrowded slopes to nordic and alpine skiers and snowboarders. Lots of sunny days and fresh snow are practically guaranteed for Ashland's winter visitors. For those more inclined to the open range, Mt Ashland's sno-parks are the perfect place for sledding and snowshoeing.

Wildflowers (many of which are endemic and very rare) begin to bloom in the lower altitudes in February and March. The Native Plant Society leads walks throughout the Rogue Valley on Saturday mornings.

Birding is a popular Ashland pastime. The Klamath Bird Observatory is well-known for its work tracking migration patterns. In nearby Klamath, thousands of migrating Bald Eagles meet up for a winter break, creating the largest congregation of this species in the continental US.

20110624_Green_Show_0003_2Photo Oregon Shakespeare Festival 

Oregon Shakespeare Festival

"The Feast of Will", celebrates summer and the opening of the OSF's outdoor Elizabethan theater plays and the pre-performance Green Show on "the Bricks" in front of the Bowmer Theater. As the weather warms, there are more outdoor performances and recreation activities to enjoy including...

156_0456-RAW-brit-floyd-britt-festivalPhoto by Al Case, Ashland Daily Photo 

Britt Festival

This epic outdoor music festival takes place from June through early September in nearby Jacksonville. The Britt's diverse and eclectic lineup is loaded with nationally known artists covering all musical genres from classical, folk, and rock, to bluegrass, ethnic, and pop. Performances take place in the Britt's open-air amphitheater known for its great acoustics and beautiful night skies. Bring your own picnic and enjoy a concert under the stars!


Alpine wildflowers blossom into an abundant display of color in the higher elevations on Mt Ashland, the Cascasde-Siskiyou National Monument, Pilot Rock, Mt. Grizzly, and Lithia Park.

Ashland's Old Fashioned 4th of July celebration has been a valued tradition for over 90 years. The day begins with a run and parade through downtown on Main St., followed by a fair in Lithia Park with food, games and crafts booths, street performers and music. After sunset, the festive day ends with a grand fireworks display.

Sporting Activities

Full and half-day fishing trips – many outfitters pick up at the B&Bs Rafting – white water, kayaking, jet-boat excursions and more. Mild to wild Golfing – at least 3 golf courses in the Rogue Valley Tennis – Lithia Park has public courts and there are also private clubs. Biking – many roads and trails offering easy to challenging routes.

LiquidAssets_042Photo: Liquid Assets Wine Bar

Wine Tasting

Southern Oregon has as many as 25 small vineyards and 6 wineries with tasting rooms. This region is known for Merlots, Cabernets, Pinot Gris and Chardonnay. Many wineries offer picnicking and music performances. Several local companies offer guided tours
AR-151029890Photo: Ashland Daily Tidings


Ashland loves a parade, and on Halloween local children, adults and pets alike assemble at the library and parade through downtown trick-or-treating at businesses along the way.

Lithia Park

Brisk walks in Lithia Park showcases the change in leaves.

Wine TastingSouthern Oregon has as many as 25 small vineyards and 6 wineries with tasting rooms. This region is known for Merlots, Cabernets, Pinot Gris and Chardonnay. Many wineries offer picnicking and music performances.

Smooth Jazz & Blues Festival

Held in September at beautiful Eden Vale Farm.

Outdoor Activities

Continued mild temperatures entice golfers to extend their playing season, and fly fisherman to take to the rivers.
Photo Mt. Ashland Ski Area

Although there is seldom snow in the town of Ashland, the hills and mountains around the Valley floor become a winter playground. Mt. Ashland Ski Resort offers challenging and uncrowded slopes for skiers and snowboarders.

Snow Parks

For those who love sledding, Nordic skiing and snowshoeing, the Sno-parks of Mt. Ashland, and Howard Prairie Lake are ideal. Trail maps can be found at Ranger Stations around the area, and at hiking and outdoor stores in town.

Holiday Shopping

Downtown Ashland’s many galleries and stores make the town a great destination for a fun and easy-going holiday shopping excursion, with unique gifts to be found at every turn. The holiday season gets ushered in with yet another celebration, the Festival of Light, which starts Thanksgiving weekend with Santa’s Parade and the lighting of trees and downtown building facades; from then until after New Year’s, downtown Ashland is transformed by pixie lights.

Ice Skating

From the first snap of cooler weather until the first signs of spring, you can enjoy ice-skating in Lithia Park.
Photo Sean Bagshaw, Outdoor Exposure

For many of our visitors the “Ashland Experience" is three-fold:

Come for first rate theater, stay at a lovely B&B and dine at fabulous restaurants. Can it get any better than that? It might be hard to believe, but in a word: YES!

Theatres, art galleries, parks, shops, museums, day spas and historic neighborhoods -- all nestled downtown at the base of the Siskiyou Mountains -- are the charms of Ashland. If you're willing to jump in your car for some short day trips, you can expand your experiences by visiting such area attractions as Crater Lake, Jacksonville, and the Britt Music Festival, plus the Rogue Valley's many wineries, antique shops, and Harry & David.

Discover what wine lovers from around the world are learning -- Southern Oregon is wine country!  For more information on local wineries and where to visit go here.

Ashland is a performing arts town! There are at least five "Off Bardway" theaters, as the locals fondly refer to the wonderfully innovative and avant-gard theater companies in the Rogue Valley; many of these theatres run during the winter months or have shows on Monday nights.

And what about those folks who love the outdoors and want more adventure? The Rogue Valley is a veritable wonderland of great terrains and natural resources for rafting, kayaking, fishing, skiing, hiking, snowshoeing, snowboarding, biking, and walking.

No matter how hard you try, it's almost impossible to describe Southern Oregon's breathtaking beauty. Visitors exploring the Siskiyou and Cascade mountain ranges will discover the rarity of flora and fauna for which they're famous. And lovers of birds, butterflies, and wildflowers will come to understand why the World Wildlife Foundation calls this area the "Galapagos of North America."
Win a Getaway
© 2018 Ashland Bed & Breakfast Network developed with a grant from the City of Ashland Lodging Tax Revenues.