Ultimate Regional Theater Road Trip

Nothing compares to live theater: the immediacy of the storytelling, the heightened emotion, the visual spectacle.

No matter how much the world might change, live theater remains a part of our shared cultural heritage — whether it be an exciting new perspective or a fresh take on an old favorite.

From coast to coast, there are tons of great theater festivals to choose from. Visit one, or make a pilgrimage to them all. To help you plan your adventure, we’ve created the ultimate regional theater road trip.

People have been telling stories on stage for a very long time.

When was the first theater performance? Nobody knows for sure, but records show plays had been produced by the Greeks as early as 534 B.C., and by the Egyptians as early as 1980 B.C.

How to Dress for a Night at the Theater

Over the years, a lot of customs, traditions, and superstitions have come to surround live theater.

So besides choosing which play to see, you might ask, “How should I dress for the theater?”

Expectations about what to wear and what not to wear to a play have become a lot more casual. But these days, there aren’t many reasons besides weddings and funerals to dress up. So why not make a night at the theater a special occasion?

Here are some suggestions for what to wear on our ultimate regional theater road trip:

  • Go formal: If you’re attending a production on opening night, or if you’re heading to the opera, choose formal attire.
  • Make it special: When planning a trip to the theater, make it special. Wear what you might wear to a wedding or job interview.
  • Accessorize: If you choose to go formal for a night out at the theater, don’t forget to accessorize. However, avoid oversized or extra gaudy jewelry. And don’t forget! Cell phones ≠ allowed. Don’t be that person — turn them off! (If you’re sitting far away from the stage, or if you have vision issues, binoculars are acceptable theater accessories.)
  • Keep it casual…but casual doesn’t mean sloppy: If you’re choosing a casual look, think dinner at a nice restaurant, not an afternoon binging Netflix.
  • Stay comfy: You’re going to be sitting down for a few hours — so make sure your clothes are comfortable. Wear clothes that fit well and don’t chafe. 

Whether you choose formal or casual, don’t forget to bring some extra layers. Regardless of the weather outside, theaters can either be chilly, or a little stuffy with all those people gathered in the same place.

With this information, your look is complete. So break a leg! Wait, why do people say that, anyway?

Theater Traditions and Superstitions

Here’s the background on a few commonly used theatrical sayings and traditions.

“Break a leg”

Nobody knows for sure why it’s common in theater to say “break a leg” as a means of saying good luck before a theatrical performance.

However, references to “breaking a leg” in theater go way back. The origin of the saying could come from an old slang term, breaking a leg, meaning to bow or curtsy.

Additionally, Ancient Greek theater audiences didn’t clap to show their approval, they stomped — stomp long enough, and they would “break a leg.”

Always turn on the ghost light before leaving the theater

Entering a stage in the dark can be dangerous due to props, set pieces, and open trap doors.

But some believe that leaving the “ghost light” on in a theater either wards off spirits or gives “diva” spirits a light in which to perform.

Mirrors onstage are bad luck

Many people are familiar with the old superstition about seven years’ bad luck after a mirror is broken. But why is having mirrors onstage bad luck?

Unfortunately, the explanation behind this superstition isn’t about how mirrors capture the soul of the audience, or anything as supernatural as that.

Mirrors, quite simply, reflect light, creating issues for any carefully designed theatrical light show.

Now, the only thing you need to do is pick a theater festival to attend from our ultimate regional theater road trip.

But first, a note about spelling.

What’s the difference between “theatre” and “theater,” anyway? Maybe you’ve noticed the word spelled both ways.

“Theater” is the preferred American English spelling of the word, while British English spells it “theatre.” Throughout our ranking, we stuck with “theater” unless “theatre” was used in the proper name of a building or production company.

Got it? Good. Now back to our program.


When setting the course for our ultimate regional theater road trip, we selected theater festivals from all across North America that first and foremost made sense to the routing of our journey.

When evaluating each festival, we considered the following:

  • How often the festival appears on similar lists and rankings from reputable sources all over the internet
  • The festival’s mix of new and classic plays, as well as the integration of any other mediums, such as music, dance, or digital art
  • The festival’s focus on diverse perspectives in their productions

All told, we’ve selected 20 of North America’s very best theater festivals. Attend just one or visit them all!

Either way, we’ll see you at the show.


Oregon Shakespeare Festival | Ashland, OR

Where to Stay: The Peerless

Begin your ultimate regional theater road trip at the Oregon Shakespeare Festival (OSF) located in beautiful Ashland, OR.

Founded in 1935 by Angus Bowmer, OSF runs every year from March through October, offering up to 850 evening and matinée performances.

Depending on the time of year, OSF presents up to 11 plays, six days a week. Plays rotate daily. In 2015, the festival drew its 20 millionth visitor. Plus, scenic Ashland offers great pre- and post-show shopping, dining, and other entertainment.

Since its inception, the Oregon Shakespeare Festival has gone from presenting works from the Shakespeare canon to classics from Africa and Asia.

The festival also commissions new works, striving to broaden live theater’s appeal for new generations and otherwise underrepresented populations.

OSF productions frequently integrate dance, music, and other forms of multimedia.

The jewel in the Oregon Shakespeare Festival crown is the outdoor Elizabethan Theater, the U.S.’s first Elizabethan-style theater.


San Francisco International Arts Festival | San Francisco, CA

Where to Stay: Hotel Nikko San Francisco

From Ashland, head south on I-5. Your destination: San Francisco, home of the San Francisco International Arts Festival (SFIAF).

SFIAF is an amazing showcase of all kinds of performing arts, including live theater, dance, comedy, and more.

Since 2003, SFIAF has sought to promote diversity, equality, and activism in a variety of different performances, presented over a three-week period at the Fort Mason Center for Arts & Culture.

Over the years, 100 presenting partners have helped present roughly 370 arts ensembles, originating from the Bay Area as well as over 56 countries around the world.

For many of the international artists, it has been their first time performing in the U.S.

SFIAF’s 2019 theater program includes new works from the U.S., Syria, Germany, and the Czech Republic.


TheatreWorks Silicon Valley New Works Festival | Palo Alto, CA

Where to Stay: Creekside Inn

It’s a relatively short hop from San Francisco to Palo Alto, CA.

Best known for tech innovation, Palo Alto also offers live theater at the TheatreWorks Silicon Valley New Works Festival, the third stop in our ultimate regional theater road trip.

TheatreWorks, founded in 1970, presents live theater all year long with performances dedicated to the discovery and development of new voices in American theater, displaying core values of artistic excellence, diversity, and innovation.

Performances are held in the Mountain View Center for the Performing Arts and at the Lucie Stern Theatre.

Running for about two weeks every August, Theatreworks’ New Works Initiative was launched in the early 2000s, featuring a writers retreat, developmental workshops and readings, as well as the New Works Festival.

In addition, TheatreWorks commissions new work, as well as main stage world premieres. Now, TheatreWorks is known throughout the theater world for its dedication to new voices and diverse perspectives.


Utah Shakespeare Festival | Cedar City, UT

Where to Stay: Big Yellow Inn

Heading east from Palo Alto, our ultimate regional theater road trip brings us to Cedar City, UT.

Since 1962, the Utah Shakespeare Festival has been held on the Southern Utah University Campus in the Adams Memorial Theater, a replica of Shakespeare’s Globe Theatre.

The Utah Shakespeare Festival, one of the U.S.’s oldest Shakespeare festivals, produces an eight show repertory season in the summer and fall of each year.

Four of the plays are usually works by Shakespeare or his contemporaries, while the rest are either classics from other eras or newer plays, with one musical generally in the mix.

In 2000, the Festival won America’s Outstanding Regional Theatre Tony Award. In 2001, it received the National Governors Association Award for Distinguished Service in the Arts for Artistic Productions.

In addition to plays, the Festival produces The New American Playwrights Project (NAPP), a “plays in progress” series, comprised of staged readings of new plays.

There’s also an educational component to the Utah Shakespeare Festival, featuring everything from week-long camps to two-day courses — most of which qualify for college credit.


Colorado New Play Festival | Steamboat Springs, CO

Where to Stay: The Steamboat Grand

Heading east from Utah, set your course for Steamboat Springs, CO, the fifth stop on our ultimate regional theater road trip.

Held in early June, the Colorado New Play Festival helps artists and theater companies from all over the country create new works for the stage.

Now in its 21st season, the festival is considered a leader in the area.

In fact, the New York Times called the Colorado New Play Festival a “top North American theater festival.”

Theater companies from all over the U.S. show stage readings of new work at the festival, and more than 70% of the new work presented moves on to regional and New York stages.

The 2019 season’s works deal with themes ranging from immigration to the horrors of seventh grade, as well as a new work about the crumbling of a black political dynasty, presented by Chicago’s legendary Steppenwolf Theater Company.


Colorado Shakespeare Festival | Boulder, CO

Where to Stay: St. Julien Hotel and Spa

Staying in Colorado, our road trip’s sixth destination takes us to Boulder, home of the University of Colorado and the Colorado Shakespeare Festival (CSF).

The CSF is a professional theater company working in association with the University of Colorado Boulder.

Over the course of 60 seasons, the festival has explored and celebrated Shakespeare’s continuing influence on and relevance to our everyday lives.

This exploration not only takes the form of live theater performances in the summer months, but also community engagement and education.

While the CSF tends to stick to the Shakespeare canon, it does offer a chance to see rarely performed Shakespeare plays like “King John.” It’s also staged a production of a new work called “King Charles III,” a futuristic play written in Shakespearean verse examining privacy issues and threats to free speech.


American Players Theatre | Spring Green, WI

Where to Stay: Spring Valley Inn

Our journey now takes us from Colorado to the American Midwest — Spring Green, WI, to be exact, where the American Players Theatre (APT) presents plays annually from May through October.

Each year, nine plays are produced in rotating repertory from May through October. American Players Theatre ranks as the country’s second largest outdoor theater devoted to the classics.

Founded in 1980, APT’s productions take place in two theaters. One, a newly renovated 1,089-seat outdoor amphitheater, the flagship “theater on the Hill,” allows spectators to take in great works under the stars in the middle of all sorts of natural beauty.

The theater’s lobby is even on the top of the one-fourth mile walking path! Don’t worry, shuttles are available.

APT’s other facility, called the Touchstone Theatre, is a 201-seat indoor space to explore new works for the stage.

There’s also a rich educational side to APT, with student matinée series, workshop residencies, children’s camps, and more.

And there is a lot for nature lovers to do at APT besides see plays, with 110 acres of walking trails to enjoy.


Shaw Festival | Niagara-on-the-Lake, CAN

Where to Stay: Brancliff Inn

From Wisconsin, we leave the country entirely. The Shaw Festival, located in Ontario, Canada, was inspired by the life and works of Irish playwright George Bernard Shaw.

The festival began in 1962, with its first permanent home, the Festival Theatre, opening in 1973.

At first, the repertory theater drew acclaim for reviving or producing plays that other companies were unwilling or unable to produce.

Since then, the programming has diversified, emphasizing the work of women playwrights of Shaw’s period, as well as modern writers carrying on Shaw’s legacy.

The festival also commissions new adaptations of Shaw’s work by many of Canada’s most respected playwrights.

As of 2018, The Shaw now operates three theater spaces — the Festival Theatre, Royal George Theatre, and Jackie Maxwell Studio Theatre.

In 2019, the festival offers a diverse playbill that includes “Sex” written by Mae West (yes, that Mae West), the murder-mystery “Rope,” and “Victory,” described as “the most offensive play you haven’t yet seen.” Other performances this season include “Brigadoon,” several adaptations of works by C.S. Lewis and Charles Dickens, and special presentations of George Bernard Shaw classics.


4 Freedoms Festival | Arlington, VT

Where to Stay: Arlington Inn

The 4 Freedoms Festival is a new interdisciplinary arts festival inspired by Franklin Delano Roosevelt’s 1941 speech to Congress outlining four essential human rights: freedom of speech, freedom of worship, freedom from want, and freedom from fear.

This speech inspired iconic American artist Norman Rockwell to create a series of paintings themed around those four freedoms.

In 2018 — the 75th anniversary of Rockwell’s paintings — the 4 Freedoms Festival was founded to both celebrate Rockwell’s work and update FDR’s four freedoms for modern and diverse audiences.

Held in Arlington’s historic Mill, a nonprofit arts venue built in the late 18th century, the 4 Freedoms Festival presents works like a new musical called “Perfect Picture,” inspired by the life of Norman Rockwell.

Other works, such as pop-up exhibitions at the nearby Bennington Museum, are also presented.


Pennsylvania Shakespeare Festival | Center Valley, PA

Where to Stay: Historic Hotel Bethlehem

From Vermont, our ultimate regional theater road trip takes us to Center Valley, PA where for 27 years the Pennsylvania Shakespeare Festival (PSF) has performed on the campus of DeSales University.

PSF is the official Shakespeare festival of the Commonwealth Classic Theatre Company, a professional theater company with core values of quality, Shakespeare, education, and relationships.

Every year, up to 50,000 patrons attend PSF from over 30 states. The Pennsylvania Shakespeare Festival has presented over 200 plays (including 30 of Shakespeare’s 38 plays), musicals, world classics, contemporary comedies, dramas, and children’s shows.

In addition to presenting classic and contemporary works, PSF provides educational opportunities, professional training, and internship opportunities to students in the DeSales Theatre program, as well as students from around the country.

In 2019, PSF presents classics from Shakespeare, like “Henry IV Part 1,” as well as “The Adventures of Robin Hood and Maid Marian” and even something for the whole family, called “Shakespeare for Kids.”


Shakespeare & Company | Lenox, MA

Where to Stay: Blantyre

From Pennsylvania, set your course for Shakespeare & Company, a theater festival held every year in Lenox, MA in the Berkshires of western Massachusetts.

Founded in 1978, Shakespeare & Company operates year round. It’s one of the largest Shakespeare festivals in the country, drawing over 60,000 patrons annually, with a core company of over 150 artists.

Since 2000, plays have been presented in one of three theaters: the Tina Packer Playhouse, the Elayne P. Bernstein Theatre, and the tented outdoor Rose Footprint.

The festival presents not just Shakespearean plays, but stage classics from all eras, as well as new works touching on contemporary social and political issues.

The Company offers one of the country’s most extensive actor training programs, and also features an award-winning, nationally recognized theater-in-education program.


Williamstown Theatre Festival | Williamstown, MA

Williamstown Theatre Festival in Williamstown, MA

Where to Stay: Maple Terrace Motel

A short drive from Lenox is Williamstown, MA, where the Williamstown Theatre Festival has presented works on the Williams College campus since 1955.

Notable actors to pass through the award-winning theater festival include Sigourney Weaver, Paul Giamatti, Gwyneth Paltrow, and Matthew Broderick.

The mission of the festival, sometimes referred to as WTF, is to produce both classics and new works for the stage and present artists with rare production opportunities and challenges.

In addition to producing plays, WTF also serves as a training program, where emerging theater talent can collaborate with accomplished mentors in a creative and professional setting.

Most of all, WTF presents programs that serve and engage diverse communities.

Several productions that began life at WTF found their way to Broadway, and in 2002 the festival won its first Tony for Outstanding Regional Theatre.


Barrington Stage Company | Pittsfield, MA

Where to Stay: Hotel on North

The next stop on our ultimate regional theater road trip keeps us not only in Massachusetts, but in the Berkshires, home of the Barrington Stage Company in Pittsfield, MA.

For nearly 25 years, the Barrington Stage Company has presented works on three stages located in downtown Pittsfield.

Each year, both the productions and comprehensive educational programming attract nearly 60,000 audience members.

Since its inception in 1995, BSC has produced 32 new works under its New Works Initiative in a two-pronged approach.

First, there’s the Music Theatre Lab, where musical theater writers’ new works are workshopped, developed, and performed. The workshop has produced seven world premiere musicals.

There’s also PlayWorks, the first home of several new plays that have gone on to Broadway and other regional stages across the country.


Westport Country Playhouse | Westport, CT

Where to Stay: Delamar Hotel Westport

Leaving Massachusetts behind, our ultimate regional theater road trip continues on to Westport, CT. Founded in 1931, the Westport Country Playhouse presents new and classic works in a converted 19th-century tannery.

In 2019, the Playhouse presents “In the Heights,” with music and lyrics by Lin-Manuel Miranda.

In addition to a full production schedule, the Playhouse also offers robust educational services such as internship and apprentice programs, boasting alumni like the illustrious Stephen Sondheim.

Additionally, the Joanne Woodward Internship Program provides summer and school-year internships to students from all over the country aged 19 years and older.

Well-known actors who’ve passed through the Westport Country Playhouse include Jane Fonda, Liza Minnelli, and a whole lot more.


United Solo Theatre Festival | New York, NY

Where to Stay: Hotel Edison

Home to Broadway, New York City is in many ways the beating heart of American theater. It’s also the 15th stop in our ultimate regional theater road trip.

Our destination this time is the United Solo Theatre Festival (USTF), now in its 10th season at the core of the New York theater district.

Over the past decade, USTF has produced more than 1,000 one-person plays. United Solo also offers master classes and gatherings for those interested in all sorts of solo performance styles, such as storytelling, puppetry, dance, multimedia, documentary, musical, improv, stand-up, poetry, magic, performance art, and drama.

The educational component of the world’s largest solo theater festival comes in the form of the United Solo Professional Training Program, a series of master classes led by distinguished artists and cultural icons.

Open to all ages and experience levels, these courses teach movement and voice, as well as writing workshops, professional development, directing, and training in specific acting techniques.


Powerhouse Theater | Poughkeepsie, NY

Where to Stay: Buttermilk Falls Inn

From New York City, our road trip brings us to upstate New York and the Vassar College campus, home to the New York Stage and Film Powerhouse Theater program.

The objective of the program, with performances running every year from late June to July, is to provide room to workshop and develop new works of film and theater.

A collaboration between Vassar College and New York Stage and Film, the Powerhouse Theater program includes fully produced plays, musical workshops, and readings of works in progress.

Additionally, the Powerhouse Theater Training Program gives aspiring theater professionals a chance to immerse themselves in acting, directing, and playwriting.

Some Broadway shows that were first presented with the Powerhouse Theater program include the 2016 Tony Award winners “Hamilton” and “The Humans,” as well as the 2016 Tony Award nominee and 2016 Outer Critics Circle Award winner “Bright Star.”


Finger Lakes Musical Theater Festival | Auburn, NY

Where to Stay: 10 Fitch Inn

From Poughkeepsie, set your coordinates for Auburn, NY, home of the Finger Lakes Musical Theater Festival.

First, the Merry-Go-Round Playhouse series brings off-Broadway productions to the newly renovated Auburn Public Theatre.

There’s also the PiTCH series, which supports the development of next-generation musical theater. PiTCH productions take place in Theatre Mack, also recently renovated, located behind the Cayuga Museum of History and Art.

In 2015, the two series struck a partnership to enhance the educational and training opportunities provided by the festival. Since then, the Youth Theatre has grown into the nation’s largest resident touring youth education program.

The Festival’s 2019 season includes “Loch Ness, A New Musical,” as well as old favorites like “Grease” and “South Pacific.”


Chautauqua Theater Company | Chautauqua, NY

Where to Stay: Athenaeum Hotel

The last New York state destination on our ultimate regional road trip brings us to Chautauqua, NY, home of the Chautauqua Theater Company (CTC).

Founded in 1983, this festival presents the best in classical theater, contemporary works, and new plays every summer at Chautauqua’s Bratton Theater.

Past productions have included works by Shakespeare, as well as new play workshops. In fact, play development is a priority for CTC, with the New Play Workshop producing staged readings of new work.

There’s also an educational component to CTC, with apprenticeship opportunities, an acting conservatory, and a design and directing conservatory.

In 2019, CTC presents Shakespeare’s “A Midsummer Night’s Dream,” and “The Christians” by Lucas Hnath.

The festival also produces community programming, like “Bratton Late Night Cabaret,” and “Free Chautauqua Shakespeare in the Park.”


Contemporary American Theater Festival | Shepherdstown, WV

Where to Stay: Thomas Shepherd Inn

Leaving New York state brings us to the American South.

Our destination is Shepherdstown, WV, home of the Contemporary American Theater Festival (CATF), hosted on the Shepherd University campus.

Founded in 1991, CATF has produced 121 new plays, including 47 world premieres by 85 American playwrights.

What’s more, 50% of all the plays produced are from women writers.

Each year, the festival sells roughly 18,000 tickets to nearly 6,000 patrons.

Educational opportunities at the festival include HostelYOUTH, CATF’s immersion program for high school students, and the The Dramatists Guild Fund, a national outreach program sending prominent dramatists across the country to give students, theater professionals, and theater fans firsthand experience with renowned artists.

CATF also welcomes college students to Shepherd University to see shows while providing affordable housing, meal options, workshops, discussions, and artist meet and greets.


Piccolo Spoleto Festival | Charleston, SC

Where to Stay: The Spectator Hotel

The last stop on our ultimate regional theater road trip brings us to Charleston, SC, home of the Piccolo Spoleto Festival.

But Piccolo Spoleto isn’t just a theater festival.

In fact, programming at this multi-disciplinary arts festival includes everything from craft shows to film screenings to poetry readings.

The festival prioritizes accessibility for both performers and audience members, and many events are free. A group of 40 working arts professionals serve as volunteer program coordinators for the festival, each specializing in a particular discipline, genre, or period.

The live theater component of the festival includes performances at a variety of venues. Productions that have been shown at the festival include “Shrek the Musical Jr.” and “A Festival of 10-Minute Plays.” Elsewhere, Piccolo Fringe at Theater 99 tackles contemporary subjects with edgy new work.