Fantastic Things To Do In Beautiful Ashland

Jamie Linger

Table of Contents Things To Do In AshlandAttend The Oregon Shakespeare Festival (OSF)Enjoy The Natural Beauty Of Lithia ParkAdmire The Public Art CollectionTake A Walking History Tour Of Ashland Sip The Water At Lithia Fountains Visit The Schneider Museum Of ArtExplore How Science Works At An Interactive MuseumAdmire Architecture And Historical BuildingsEnjoy […]

Ashland is known for the Oregon Shakespeare Festival, but there are other hidden gems to discover in this delightful city. Ashland is nestled in a valley between the Cascade and Siskiyou mountain ranges in southeastern Oregon, a mere 15 miles from the California Border. 

The city of Ashland boasts of several awards, including ranking in the top 10 of Best Small Towns in America, one of the Top 10 Places to Visit, and one of the Top Ten Best Outside Towns To Live.

The nearest major airport, Rogue Valley International (MFR), is located in Medford, only 15 miles away. Or, one can enjoy the drive from either Portland or San Francisco. Ashland is located halfway between these two cities.

From beautiful mountain scenery to award-winning wines and restaurants, craft breweries, walking tours, boutique hotels, local history, and public art, join me on a glorious weekend in Ashland.

I was hosted for two days by Travel Ashland. All thoughts and reflections are my own.

Chris Allan /

Things To Do In Ashland

Attend The Oregon Shakespeare Festival (OSF)

Ashland hosts the renowned Oregon Shakespeare Festival, one of the oldest and largest repertory theaters in the United States. The season runs from mid-February to early November with productions in three theaters: Angus Bowmer Theatre, Allen Elizabethan Theatre, and Thomas Theatre. You can enjoy the Green Show during the summer evening performances, a half-hour courtyard production featuring guest performers. Backstage tours, as well as educational discussions, are available. Be sure to also stop by the Visitor Center, where you can ask questions, try on costumes, and learn about OSF history. Also visit the Tudor Gift Shop for unique gifts.

Lithia Park in Ashland, Oregan.
Sean Bagshaw Outdoor Exposure Photography / Travel Ashland

Enjoy The Natural Beauty Of Lithia Park

Called Ashland’s Crown Jewel, Lithia Park is a 100-acre site right off downtown. In 2014, it was honored by the American Planning Association as one of the Top Ten Great American Spaces. There is something for everyone, with trails, benches, picnic sites, water features, gardens, tennis, pickleball, and volleyball courts. From May through September, you can enjoy a morning guided walk by a trained volunteer naturalist. 

Click this link for a downloadable trail guide.

Mural tribute to the sister city, Guanajuato, Mexico.
Jo-Anne Bowen

Admire The Public Art Collection

Spend a morning admiring the public art collection, including sculptures, mosaics, murals, and fountains. Click this link for a downloadable map. Three of my favorites are We Are Here, the bronze replica of the sculpture honoring the indigenous peoples of southern Oregon. The original is now located in the Library of Southern Oregon University. I also enjoyed the mural and story of Las Calles de Guanajuato, commemorating the 50th Anniversary of Lithia’s sister city relationship with Guanajuato, Mexico. Look also for Street Scene, the 14-foot-tall bronze sculpture by Marion L.Young. It features 12 people and three Shakespeare characters. Local townspeople served as models.

Tall sculpture of men and women  out on the streets of Ashland, Oregon.
Jo-Anne Bowen

Take A Walking History Tour Of Ashland 

Enjoy learning about the history of Ashland on a walking tour with a local expert, such as Peter, from Walk Ashland. I give it a hearty recommendation! The guided tours last from one to two hours with a maximum group size of 12. The first tour to be offered is called Plaza & Founding of Ashland. Customized tours can also be arranged.

Also, from June through October, local historian Terry Skibby conducts Friday morning walking tours of the Historic Railroad District. 

If a self-guided tour is more your cup of tea, check Story Maps, an online resource with information and maps.

Famous Lithia Fountains in Ashland, Oregon.
Jo-Anne Bowen

Sip The Water At Lithia Fountains 

Lithia waters are believed to have healing powers. Early Native Americans used the waters for their sick and elderly. At one time, near the beginning of the 20th century, there was hope that the Ashland area could become the center of a healing spa similar to those in some European countries. Costs for the water pipeline became prohibitive, and along with WWII, such interest was lost. Stop at the Lithia Fountains in the Downtown Plaza to sip some of these acclaimed healing waters. 

Glass panel entrance to the Schneider Museum of Art, located on the Southern Oregon University campus.
Chris Allan /

Visit The Schneider Museum Of Art

Located on the Southern Oregon University campus, the Schneider Museum of Art has its mission of “making exhibitions and events accessible to all.” As such, there is no admission fee!

A variety of tours are offered for folks of all ages and abilities. To request a tour, complete a tour request form. You can also attend a drop-in tour every Tuesday at 12:30 p.m. No registration is required for the free Tuesday tours.

Explore How Science Works At An Interactive Museum

Spend an afternoon at ScienceWorks, where guests of all ages explore science through interactive experiences. There is also an excellent online program where one can learn about the contributions of notables such as Dr. Jane Goodall, Dr. Lonnie Johnson, and NASA mathematician Katherine Johnson, whose career was profiled in the movie Hidden Figures

Carnegie Library building 1912, restored 2003, now serves as the Children's Library, located in Ashland, Oregon.
Underawesternsky /

Admire Architecture And Historical Buildings

The entire city center of Ashland is on the National Registry of Historic Places. 

Admire the architecture of the IOFF building, also known as the Oddfellows building. The building dates back to 1879.

Pause also at the Carnegie Library, built in 1912 and restored in 2003. Of the 31 Carnegie Libraries built in the state of Oregon, only 11 are still in use. Ashland’s Carnegie Library is one of these 11.

If you are strolling the downtown area on weekends March 15 through October 31, look for the Lithia Artisans Market, an outdoor arts and crafts market. You can meet local artists and craftspeople who sell their products from over 40 booths located along the creek.

Enjoy A Performance At The Oregon Cabaret Theatre

Enjoy live theater, cabaret-style, and gourmet dining at Oregon Cabaret Theatre. Now in its 30th year, the season runs from February through December. Ordering food or drinks is optional. Desserts are served only during intermission. Be sure to try Dick Hay Pie, a mouthwatering combination of ice cream, peanut butter filling, chocolate, and pie crust. Scrumptious!

For information on upcoming productions, click this link.

Caldera Brewing Company dinning room and bar top.
Agave Photo Studio /

Sip Craft Beers

Sip finely crafted brews at one of Ashland’s craft breweries. Caldera Brewing Company offers unique brews like Toasted Coconut Chocolate Porter and Mother Pucker Raspberry Sour Ale. Enjoy the lovely mountain scenery and grab a bite at the restaurant. Check out the 4,600 items in the beer and can collection.

Standing Stone Brewing Company offers seasonal and year-round brews and an extensive pub menu and company store with unique gifts. The company’s commitment to sustainability and intelligent resource use has led them to be honored as one of Oregon’s 100 Best Green Businesses.

Attend The Ashland Independent Film Festival (AIFF)

Film lovers will delight in the nationally accredited Ashland Independent Film Festival. The AIFF main event is held each April when filmmakers from around the globe meet to view documentaries, features, and short films. There are also forums and screenings as well as year-round activities celebrating independent films. You can sign up for the newsletter to keep abreast of the latest happenings.

Lithia Park trails in Ashland, Oregon.
Lithia Park Trails (Nadia Yong /

Enjoy Hiking And Biking

With 50 miles of trails and 18 parks, there is a trail for everyone’s abilities — pedestrian or cycling. Click this link for maps from Ashland Trails Association. 

Rolling hills of Irvine & Roberts Vineyards.
Jo-Anne Bowen

Sip Excellent Crafted Wines In Beautiful Vineyards

Visit the Irvine & Roberts Vineyards to enjoy finely crafted wines in a beautiful setting. Located a mere 5 miles from downtown Ashland, the site features a tasting bar, fireplace, floor-to-ceiling windows, and a large patio area. Take time to enjoy their story and how they “learned very quickly to listen to [their] plants.” A talented chef prepares small bites to complement the wines. 

The courtyard of Peerless Restaurant & Bar in Ashland, Oregon.
Jo-Anne Bowen

Best Restaurants In Ashland

The culinary scene in Ashland features various coffee shops, cafes, and restaurants sure to please your taste buds.

For casual dining, consider Brickroom Restaurant & Bar, honored with the title Top Chef in 2017. The Greenleaf Restaurant presents casual creekside dining and picnic and boxed lunches.

Peerless Restaurant & Bar, located in the historic Railroad District, is recognized as one of southern Oregon’s premier dining destinations. Enjoy dining in the lovely courtyard set amongst fountains and shrubs, named one of the Best Outdoor Dining Spots in Ashland.

Larks Home Kitchen Cuisine at Ashland Springs Hotel is another award-winning restaurant in a beautiful historic setting. 

Watch also for annual culinary events, including the Ashland Culinary Festival and the Oregon Chocolate Festival.

Best Hotels In Ashland

From boutique hotels to historic inns, Ashland has a variety of comfortable accommodations. 

We enjoyed a lovely suite at Plaza Inn & Suites. The location is ideal, within walking distance of Lithia Park, the theater district, and numerous restaurants. The spacious, welcoming lobby is furnished in a Shakespearean theme. 

The historic Ashland Springs Hotel is a downtown landmark dating back to 1925. The beautiful refinished interior has been featured in Architectural Digest. Take time to study the various collections in the lobby.

With all that Ashland has to offer visitors, one weekend probably will lead to more! Plan a visit soon.

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