Experiencing the Oregon Shakespeare Festival in Ashland

Oregon Shakespeare Festival in Ashland

Experiencing the Oregon Shakespeare Festival is one of the best things to do in Ashland. This is everything you should know before you go!

All the world’s a stage, and all the men and women merely players: they have their exits and their entrances; and one man in his time plays many parts, his acts being seven ages.” – William Shakespeare

Shakespeare is a writer I’ve always loved and quoted. People may say his plays are antiquated and irrelevant, but I find the opposite to be true.

I find his plays to be some of the few that translate well to modern times, especially when you have productions like the Oregon Shakespeare Festival, updating and revamping Shakespeare and his contemporaries constantly.

From the moment I was first introduced to my local Shakespeare Santa Cruz production of King Lear when I was a little girl, I’ve dreamed of going to the Oregon Shakespeare Festival in Ashland.

I already knew that Ashland was the best Shakespeare town in Oregon, and I imagined it to be this beautiful place with constant fall foliage. The perfect backdrop to watch Shakespeare come to life.

When I made it to Ashland for the first time at the age of 25, I was not disappointed by my childhood dreams of attending an Oregon Shakespeare Festival production (or two!).

ashland shakespeare festival
Photo by Jenny Graham.

Note: this post contains affiliate links, which help run this site at no extra cost to you so I can keep providing free travel advice and tips. 

OSF Ashland History

The Ashland Shakespeare Festival began in 1935 by Angus L. Bowmer, and has only continued to produce phenomenal actors, plays, and has won Tony Awards as proof of its caliber.

The first Elizabethan stage in America was constructed where the Ashland Oregon Shakespeare Festival now takes place, and its first production was on July 2nd in 1935, showing the classic, Twelfth Night.

Throughout the course of its existence, the OSF has put on all 37 Shakespeare plays, as well as original productions and other famous productions from other playwrights.

My Experience at OSF

I was lucky enough to attend two plays in Ashland, Oregon: Guys and Dolls and the new favorite, Head over Heels.

My first night I went to see the riveting Guys and Dolls at the indoor Angus Bowmer Theatre. I had seen Guys and Dolls once before at a school production at UC San Diego, but the one I saw put on by the OSF blew me away.

Related: Top 7 Things to Do in Ashland, Oregon

ashland theater
Sky Masterson (Jeremy Peter Johnson) and Ensemble. Photo by Jenny Graham.

I’ve always been enamored with early 20th century New York City, and Guys and Dolls is seriously the perfect production to go see if you’re fond of that time period.

Even when it’s not one of the famous Shakespeare plays, OSF knows how to put on a bawdy and fun show that Shakespeare would’ve definitely approved of if he was still alive today.

Originally based on the short stories from the American author Damon Runyon, Guys and Dolls is a musical adapted by Frank Loesser and created into a Broadway hit that won the Tony Award in 1950.

It’s set in the streets of New York City, with the play centered around the notorious Nathan Detroit trying to find a spot for his crap game. It’s a whirlwind of great music, whimsical plots, and two love stories intertwined.

My favorite scenes of the night were to the soundtrack of “Crapshooters Dance”, “Luck be a Lady” and “Sit Down, You’re Rockin’ The Boat”.

osf ashland
Guys and Dolls Ensemble, directed by Mary Zimmerman. Photo by Jenny Graham.

Even with OSF’s production running a grand total of 2 hours and 25 minutes (including an intermission), I was left wanting more when the curtains went down and the deafening whistles went up from the audience.

With how much I enjoyed my first night at OSF, I was in for even more of a treat the second night with Head Over Heels.

Also a musical, the premise behind the play is inspired by Sir Philip Sidney’s 16th century romance, Arcadia, and was written by Jeff Whitty with music by the Go-Gos.

And yes, if you’re wondering, it was a marvelous combination.

The production was performed in the Allen Elizabethan Theatre in Ashland, and I couldn’t believe how much energy the actors on stage had from start to finish, using every inch of the stage, interacting with audience members, and singing their hearts out.

Head Over Heels consisted of fun, irrelevant Elizabethan humor, and a laid-back but professional and confident attitude by the actors.

Even though the play was set in Elizabethan times, used music from a 1980s rock band, and touched on modern-day issues in the LGBTQ realm, everything meshed together perfectly.

There were multiple times throughout the night that I was laughing out loud and clapping along to the beat of the music.

allen elizabethan theatre
The Guys and Dolls ensemble. Photo: Jenny Graham

Overall, I had a really good time at the Oregon Shakespeare Festival, and the best part is that it’s affordable for all types of budget.

Seats are a range of prices. Obviously, the better the seats the higher the price, but you can find seats for as low as $30. There were people before every show that had a sign asking for free tickets, so that could work as well depending on whether you’re not too worried about guaranteed tickets.

The Green Show in Ashland, Oregon

In addition to the main performances, OSF offers a free Green Show most days of the week, set up outside of the Ashland theater.

The Oregon Shakespeare Festival Green Show has a stage and puts on free entertainment throughout the summer and fall from Tuesday through Sunday. When I was there, The Wild Zappers and National Deaf Dance Theater were performing.

The OSF Green Show is a great option if you still want to experience the festival but your favorite play has already sold out, or you’re on a tight budget. Shows usually last for around 45 minutes and are completely free.

You can find the current schedule for the Ashland Green Show here.

Related: Ashland, Oregon in the Fall – Why You Need to Go!

green show in ashland oregon
Photo by Jenny Graham.

As you can see, there are a lot of options depending on your time in the area and your budget. And there is honestly a play genre for everyone, unless you absolutely hate theater.

During the season I went there were 11 different Ashland Shakespeare plays, and there are always at least a few humorous Shakespeare productions thrown into the mix.

If you’re in the Ashland or Southern Oregon area, I would highly recommend experiencing Shakespeare in Ashland at least once through the festival. If you’re able to see a show at the Allen Elizabethan Theatre, even better. It was a magical experience.

Regardless of where you see the performance, you will not be disappointed with the quality. It’s the thing to do in town and very much intertwined in Ashland culture.

Practical Info for Attending OSF

How Expensive are OSF Tickets?

Ticket prices for the Oregon Shakespeare tickets range from $30 (for preview shows) to $120 (for box seats). OSF has always been an inclusive company that tries its best to make sure anyone, no matter their budget, can enjoy one of their plays.

Read below for the options on how to get tickets, depending on your budget.

How to Get Oregon Shakespeare Festival Tickets

The Easiest Way – Book Online Ahead of Time

The easiest way to get OSF tickets is to book them online ahead of time here.

It’s recommended to book tickets a few weeks ahead of time because they can sell out quickly, especially for new, original productions. Try and book a month ahead of time if possible, if you know you want to go to a popular show.

If you’re fine with going to any show that’s available, booking a few days before or the day of is fine. If you’re booking last minute tickets just choose the OSF on call tickets and pick them up from the Oregon Shakespeare Festival Box Office once you’re in Ashland.

what to do in ashland oregon

Member Tickets 

If you choose to sign up for an Oregon Shakespeare Festival membership (starting at $75), you can get up to four tickets per season at 25% off, as well as access to early pre-sale tickets and free refunds and exchanges up to seven days before the show.

Web Specials

Web specials are limited time discounts that OSF runs throughout the season for selected performances. You can look at current web specials by going here.

If you’re serious about getting the best cheap tickets for the Oregon Shakespeare Festival, it’s also a good idea to sign up for an account and register for their newsletter to have these web specials sent directly to your inbox. You can register here.

Rush Tickets and Student Rush Tickets 

If you haven’t planned ahead and you find yourself in Ashland wanting to go to a show but don’t want to spend a lot on a show, there’s the option for rush tickets.

The Oregon Shakespeare Festival box office offers rush tickets for $40 for select ‘rushing’ shows that are announced the day of the performance. The tickets are only available to purchase at the box office an hour before curtain call and they’re first come first serve.

Note: members have the added benefit of being able to call ahead on the day of a performance to inquire about rush tickets and book over the phone. Everyone else has to go directly to the box office to find out if there are any rush tickets available an hour before a show starts.

Youth (17 and under) and college students can get $17 rush tickets with the same rules as above. A valid ID is required.

Family Days 

If you’re traveling to Ashland with your family, OSF Family Days are a great option to keep things affordable and fun for the young ones.

During OSF Family Days, tickets are offered at a reduced price of $30 per person and include an interactive and educational prologue at the beginning of the performance. You must have at least one youth (6-17 years old) in your group in order to get Family Day tickets.

You can buy family day tickets here.

oregon shakespeare festival tickets

Flex Passes

If you plan to go to a handful of shows throughout the season but want to get tickets at a discounted price, the Flex Pass is an ideal option.

With the Flex Pass, you get a discounted 5-pack of ticket credits that can be used for select performances throughout the season. The cost is $175, which breaks down to $35 per ticket.

Other discounted OSF Tickets

  • Oregon Trail, CalFresh, and SNAP card holders can get tickets for $5 for select performances (you can find the full list here).
  • Youth discount – 30% off all tickets for anyone 17 and under. Must have a valid ID.
  • Military discount – 15% off all tickets for active duty US military or National Guard members and their family members, as well as veterans. There’s a limit of two discounted tickets per order. (Only valid for Sunday-Thursday performances).
  • AAA discount – 10% off all tickets. (Only valid for Sunday-Thursday performances).

How to Get from Portland to Ashland

The drive from Portland to Ashland is just under five hours. You can hop on I-5 South and take it all the way down to Ashland. If you’re coming from Eugene, the drive is only three hours.

Alternatively, if you don’t want to drive, the best way to get down to Ashland is on a Greyhound bus, which usually takes around 10 hours and costs $40.

Unfortunately, there’s no direct train from Portland to Ashland. You can take the Amtrak to Klamath Falls from Portland, but then you’ll have to hop on a bus from Klamath Falls to get to Ashland. The full trip would take 22 hours. Driving is by far the most efficient and comfortable option.

Where to Eat & Drink in Ashland

The good thing about the Oregon Shakespeare Festival being in Ashland is that the city is known for its fantastic foodie scene, in fact most of Southern Oregon is with how agricultural-focused the region is.

You’ll be able to find most of the best places to eat and drink around downtown Ashland, Oregon.

ashland restaurants - caldera brewing

My favorite place to grab coffee is Noble Coffee Roasting and the best spot to drink craft beer is at Caldera Brewery (just note that they have their tasting room in downtown Ashland but their actual brewery is outside of the city. Go to their tasting room!).

And a few of my favorite Ashland restaurants include: Morning Glory for breakfast, Sammich for lunch, and Larks Ashland or Martolli’s Pizza for dinner.

What to do in Ashland, Oregon Besides the Festival

Although the Oregon Shakespeare Festival is one of my favorite things to do in Ashland, there are so many other ways to stay busy and entertained around the city. Lithia Park, wine and beer tasting, hiking and other outdoor activities, just to name a few.

For a full list of my favorite things to do in the town of Ashland, check out this post.

Where to Stay in Ashland

Whether it’s an Ashland bed and breakfast or one of the cozy boutique Ashland hotels in town, there are plenty of options for accommodation in Ashland, no matter your budget. These are my favorite Ashland, Oregon hotels and accommodation to pick from!

ashland oregon hotels - ashland hills hotel & suites
Ashland Hills Hotel & Suites


Flagship Inn of Ashland

One of the most popular budget hotels in Ashland, Oregon, Flagship Inn offers air conditioned rooms featuring floral decor and work desks. There is also a swimming pool.

Check availability & pricing here

Note: if you’re looking for good camping near Ashland, Oregon, you can find a few options here or here.


Ashland Hills Hotel & Suites

I stayed at the Ashland Hills Hotel & Suites while I was in Ashland and was very happy with my stay. The hotel is situated a little ways outside of downtown, so best to stay at only if you have a car. Think 70’s inspired decor that is clean and modern.

Check availability & pricing here

Related: Read my full review of the Ashland Hills Hotel & Suites here.

Bard’s Inn

One of the most popular hotels in Ashland, Oregon to stay at for those who are in town for the Oregon Shakespeare Festival. Bard’s Inn is only a 6 minute walk from the Shakespeare festival, right in downtown, and offers both a pool and hot tub, as well as a quality free breakfast.

Check availability & pricing here


Winchester Inn

Part hotel, part bed & breakfast, the Winchester Inn is one of the better luxury stays you can have in Ashland. Comfy and spacious rooms with down feather beds that include 600 thread count sheets, and a free 2-course gourmet breakfast in the mornings.

Check availability & pricing here

downtown ashland oregon

Other Popular Ashland, Oregon Events

  • Mystic Rising Festival (end of June-July)
  • 4th of July Parade & Celebration (July 4th)
  • Ashland Culinary Festival (November)
  • Festival of Light (end of November)

As Shakespeare once said, “Good night, good night! Parting is such sweet sorrow, that I shall say good night till it be morrow.”

The Oregon Shakespeare Festival generously hosted me for the two plays I attended, but, as always, all opinions are my own. 



Find accommodation or book your rental car

Find out what to pack for Winter Day Hikes in the Pacific Northwest.

Buy your Pacific Northwest Travel Guide here.


Experiencing the Oregon Shakespeare Festival in Ashland, Oregon

Pin this image for future reference


Looking for more Oregon travel inspiration? Check out my related posts below! 

The Best Things to do in Florence, Oregon

Jet Boating the Rugged Rogue River

8 Things to do in Bend, Oregon in the Summer

14 Stops to Make on an Oregon Coast Road Trip

6 Unique Things to do in Grants Pass, Oregon

How useful was this post?

Click on a star to rate it!

We are sorry that this post was not useful for you!

Let us improve this post!

Tell us how we can improve this post?

Mimi McFadden
Find Me

4 thoughts on “Experiencing the Oregon Shakespeare Festival in Ashland”

Leave a Comment