2 Days in Ashland, Oregon

The Allen Elizabethan Theatre set for the Oregon Shakespeare Festival's 2013 production of A Midsummer Night's Dream. (Courtesy - T. Charles Erickson - OSF)

The Allen Elizabethan Theatre set for the Oregon Shakespeare Festival’s 2013 production of A Midsummer Night’s Dream. (Courtesy – T. Charles Erickson – OSF)

GetCurrentFast.com Travel Guide™

This travel guide presents the top things to do in Ashland, Oregon during a two-day trip at a leisurely pace. We suggest scheduling your trip during the Oregon Shakespeare Festival (OSF) which runs from late February through October. Although it is filled with many practical travel tips, we wrote this guide to be “A good read even without the going,”™ so enjoy this virtual trip.

In this  trip to Ashland, you will be enjoying world-class theater productions, the charm of a quirky small town, and the grandeur of rural southern Oregon.

William Shakespeare (Shutterstock)

William Shakespeare (Shutterstock)

Remembered as an enigmatic man, actor, playwright, poet –William Shakespeare is generally considered the greatest writer of the English language. Elements of his extraordinary body of work permeates modern culture like no other.

Understandably, the Bard, as Shakespeare is known by his admirers, is a big deal. And in the small southern Oregon town of Ashland, he is a really a big deal, for it is the annual festival in honor of ol’ Shakey that put the town on the map. The award-winning Oregon Shakespeare Festival (OSF), started in 1935, is the main draw for tourists and is the backbone to the small town’s thriving art scene.

Even if you have never studied, read, or watched anything of Shakespeare’s, it’s never too late to start. And even if you think you have been there and done that, if you have yet to watch one of his works performed underneath the stars in Ashland, we highly recommend the experience. People of all ages, and all walks of life make a pilgrimage here, and many can’t seem to get enough.

Lithia Park in Autumn (Shutterstock)

Lithia Park in Autumn (Shutterstock)

Angus L. Bowmer, an enthusiastic young teacher, is credited with first producing works of Shakespeare in the ruins of a former Ashland theatre, OSF fondly recalls on its website. The city cautiously advanced the money necessary to fund the program ($400), but insisted that boxing matches also be scheduled just in case the plays were a dud. The performances were a success, and paved the way for the establishment of OSF which is one of the largest and oldest non-profit theatre companies in the U.S.

The universality of the Bard’s plays are proven nightly in Ashland where diverse audiences are riveted by both traditional and modern adaptations of his classic plays. In the hands of the talented directors and actors, Old English is easily approachable while the timeless truths, resonating themes, and compelling characters of the plays are brought to life. Indeed, even if you’re not all that familiar with some of the classics, the staff of OSF is known for making everyone feel welcome and at home.

Although many people come for the theatre, there is much to Ashland beyond the Bard. The town is home to Southern Oregon University so it exudes the charm of an arts destination with a college town vibe, making it a very lively and eclectic place to visit.

Sign for the Elizabethan Theatre

Sign for the Elizabethan Theatre

The food scene, blessed by the bounty of the Pacific Northwest, is unexpectedly diverse and developed for a small town. Downtown is brimming with boutiques and galleries selling artisan wares. Then there is the surrounding area – Ashland is part of the Rouge Valley with the Siskiyou Mountains and part of the Cascade Range as a dramatic back drop. Aslandians have their pick of two nearby national forests: Rouge River – Siskiyou and Klamath.  And if you happen to travel during the fall, you’ll see why some claim the Rouge Valley rivals even the famed fall foliage of New England.

While you could easily spend a long time exploring all that Ashland has to offer, if you have only a few days, this guide helps you make the most of them, including a suggested itinerary and a list of Editors’ Choice restaurants.

Day 1: Explore Downtown

Lithia Park (Shutterstock)

Lithia Park (Shutterstock)

After breakfast, we suggest you start your first day in Ashland with a walk around town. Main Street and the surrounding area are brimming with boutiques, and restaurants. Don’t miss Renaissance Rose , a multistory costume shop or Tudor Guild, the official OSF shop. Stroll through Lithian Artisans Market of Ashland: here local artisans sell their work in a picturesque setting along Ashland Creek.

Your first day in Ashland would not be complete without dinner (see Editor’s Choice Restaurants below) and a show. Be sure to schedule dinner to allow a relaxing meal with plenty of time to get to the theatre.

OSF offers many different plays each season at least three of which are works of the namesake playwright. Reading a synopsis of the play ahead of the performance can help you and any young people in attendance get the most out of it. The other choices are an array of classic plays and modern works that make their debut at the festival. Many performances sell out months in advance, so plan accordingly.

Three theatres are home to the OSF productions, but the Elizabethan Stage is the most unusual; the outdoor theater emulates those of the time when Shakespeare was penning his plays. Watching one of the Bard’s works under the majesty of the Oregon night sky is certainly an experience to be remembered. Depending on the time of year, be sure to dress warmly, and consider bringing and outdoor blanket. Children must be at least 6-years-old and some of the plays are suitable for mature audiences only.

Day 2: Lithia Park

2013 Production of My Fair Lady. (Courtesy Image - OSF/Jenny Graham)

2013 Production of My Fair Lady. (Courtesy Image – OSF/Jenny Graham)

Coffee is a beloved fuel of both artists and students, so it makes sense that this artsy college town would have many fine coffee shops. It makes the job of picking the stop for your morning cup of joe a pleasant challenge. Noble Coffee Roasting, Case Coffee Roasters, and Rouge Valley Roasting Co. are local roasters who offer a fine selection for java lovers. Mix Sweet Shop serves up coffee alongside house-made desserts and breakfast pastries.

We suggest a leisurely morning creekside stroll in lovely Lithia Park. It’s named for the effervescent lithia mineral water said to have healing properties. The distinctly tasting water is featured at the grand drinking fountain near the park and is often used as an Ashland initiation rite. You can walk for a short distance or over one mile one-way. Along the way there are numerous places to sit and relax while enjoying the scenery.

We suggest lunch at one of the restaurant mentioned below before heading out for an afternoon expedition featuring one of the following activities.

  • One way to enjoy your afternoon is tasting local wines at some of the Rouge Valley Wineries
  • Alternately, take a tour of the Harry and David Factory in nearby Medford and learn how some of their candies and snacks are made.
  • If you are in the mood for some exercise, spend the afternoon hiking and enjoying the beauty of Southern Oregon (See Take a Walk, Hike, and R&R below.)
Rouge River (Shutterstock)

Rouge River (Shutterstock)

Alternatively, choose one or more of the following places to walk, hike, or just relax and recharge. Of course, you and your doctor should agree that you’re up to any physical exertion.

  • A moderate 4 mile hike takes you up Grizzly Peak and back.
  • The easy 2 mile Tunnel Ridge  hike takes you through brushy foothills.
  • It’s a strenuous 10 mile hike up Wagner Butte and back, but the stunning view is worth it.

Along the way, look for a spot to sit back and relax for a while, ideally unplugged.

Selected Day Trip

The Rouge Valley (Shutterstock)

The Rouge Valley (Shutterstock)

If you extend your trip or upon your return visit, consider making the hour and a half drive to Crater Lake National Park. Read our guide to Crater Lake here.

Editors’ Choice Restaurants

Our top picks for area restaurants are listed alphabetically below. We carefully screened them as if we were making a recommendation to our family or friends. In most popular areas, particularly during peak seasons, we suggest making reservations or at least calling ahead for wait times. Arriving early is also a good idea, and can help make the meal more leisurely and relaxing. Of course, prices and menus are subject to change.


Editors’ Choice Restaurants Meals Price
(American food unless noted otherwise)
Alchemy Restaurant and Bar $$$ The pursuit of “Alchemy”  here, is transforming local ingredients into elevated cuisine.
Amuse Restaurant  $$$ The husband and wife owners of Amuse serve up French cuisine with northwestern flair.
The Breadboard $-$$ Serves up traditional breakfast platters, as well as some inventive specials like the Triple Berry Corncakes.
Eleven $-$$ Serving up casual, local food and a selection of Rogue Valley Wines.
Granite Taphouse  $$ “Home of Craveable Food and Craft Brews”
Larks Home Kitchen Cuisine $$ “Celebrating Oregon” with their inventive menu based on seasonal, local ingredients.
Omar’s Steak and Seafood $$-$$$ “Ashland’s Original Steakhouse”
Smithfields   $$-$$$ A “meat-centric” place “specializing in ‘nose-to-tail’ dining and in-house charcuterie”
Standing Stone Brewing Company $$ Wood-fired pizzas, burgers, and craft beer is served at this local brew pub.


Map of Editors’ Picks from GetCurrentFast.com



Visitor Info

Ashland Chamber of Commerce


General: AAA Travel | America Strong | Fodor’s Travel | Frommer’sTrip Advisor, | WikiTravel | Wine Spectator, and other trusted sources

Local Facts & Trivia: 50States.com, and other trusted sources | Hiking (basic maps and reports are free): Trails.com and AllTrails.com

Restaurant Reviews: AAA Travel | Fodor’s | Open TableTrip Advisor | Urban Spoon | Zagat, and other trusted sources

Please travel and enjoy yourself responsibly —and at a leisurely pace.

Because it is subject to change, be sure to confirm the information in this guide
including the days and hours of operation for each attraction, restaurant, etc.

GetCurrentFast.com Travel Digest
A good read even without the going™

Jessica O'Malley
Jessica O’Malley, Associate Editor, writes for GetCurrentFast.com. Her work is distributed by GCF Media Syndicate. Jessica is an entrepreneur, real estate and business investor, writer, culinary artist and coach, and world wanderer. In addition to her international travels, she has been to all 50 states and is revisiting them to write about the top destinations, attractions, and restaurants in the USA.
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