It’s been said that Ashland, Oregon — known and loved as the home of the Oregon Shakespeare Festival — is a place packed with retired English teachers who came north from California. It can to be added that Ashland is a favorite vacation spot for literary and theatrical types from Olympia.

On a recent visit, two Olympia couples found themselves sitting by chance in the same row at one of the festival’s three theaters, and all agreed that it wasn’t the first time.
“It appears to be the norm for Olympia residents to drive down to Ashland for a few days every year,” said Sean Williams, a semi-retired professor at The Evergreen State College. (She teaches ethnolomusicology, not English.) “No matter when my husband and I have visited, even on one-night stopovers to or from the Bay Area, we see people from Olympia.”
People’s willingness to make a six-hour drive each year is a testament to the popularity of Ashland and the festival, which offers Shakespeare and more in repertory from March through October.
Both the festival and the town are busier than they have been since before the pandemic. The empty storefronts left in the wake of the pandemic are once again full, and so are the streets and parking spaces. Locals credit much of the resurgence to artistic director Tim Bond, who began his career with the Seattle Theatre Group.
While the plays are Ashland’s main draw, you don’t have to be a friend of Will to enjoy the festival. Of this year’s 10 shows, three — “A Midsummer Night’s Dream,” “The Taming of the Shrew” and “Henry IV, Pt. One” — are by the bard.
“Dream,” with original songs by Tacoma native Justin Huertas, is a must-see — and you don’t have to take this writer’s opinion on that. Word on Ashland’s Main Street is that this version — with Art Nouveau-style sets, gorgeous costumes and a cast with a gift for comedy, including Huertas (best known for his original musical “Lizard Boy”) as a charming Puck — is the best many people have ever seen.

Another must — at any visit to the festival — is seeing a show in the outdoor Elizabethan Theater, built in 1935. There’s something magical about seeing a show under the stars in a theater in the style of London’s Globe Theatre.
The 2026 Elizabethan shows are “Shrew,” “Henry” and Kate Hamill’s “Emma,” a lively take on the Jane Austen novel that pokes at the patriarchy and has audience members laughing and cheering,
“Henry,” with steampunk-meets-futuristic sets and costumes, adds clever staging and some high-comedy moments to the classic tale of young Hal and his outlaw friend Falstaff. The slapstick “Shrew” also has some amazing physical comedy, along with a wedding-gown-wearing Petruchio and some delightfully cheesy Italian tunes, but audience members would do well to remember that despite the distracting antics, this is still a show about a man mistreating and gaslighting his wife.
Also on stage now:
- Lorraine Hansberry’s classic “A Raisin in the Sun,” directed by OSF artistic director Tim Bond. Moving and powerful, this is a must see — if you can get to Ashland before it closes July 19.
- “You Are Cordially Invited to the End of the World,” by Keiko Green of Seattle. It’s about climate change and terminal cancer, and it’s heartbreaking, hilarious and hopeful. It’s another must see, especially for those who love new plays, and you have till Aug. 21.
- “Come From Away,” which is getting rave reviews, including from Williams, who’d previously seen two other productions. “Just as I’d done in New York and Seattle, I watched from the edge of my seat,” she said. “I cried repeatedly — but at least this time I remembered to bring tissues.”
Still to come: August Wilson’s “King Hedley II” (opens July 16), SAY MORE?; “Yellow Face” (opens Aug. 5), a Tony nominee about a Chinese-American playwright who accidentally casts a white actor to play an Asian character; and “Smote This: A Comedy About God … and Other Serious $H*T” (opens Aug. 27), Rodney Gardiner’s solo show about growing up as an undocumented immigrant.

Also on tap at the festival: free Green Shows at 6:30 p.m. Tuesday-Sunday through September, backstage tours, pre-show talks and — new this year — a beer and wine garden during a handful of shows (https://www.osfashland.org/greenshow).
While you’re planning which shows to see, leave some space in your itinerary to enjoy the many fine restaurants, visit wineries and wander the 93-acre Lithia Park, known for its sycamores, duck ponds and Japanese garden and for the impromptu concerts of cellist Daniel Sperry, who for more than a decade has been playing in the park.
Not far from Ashland is another cultural hub — the Britt Music & Arts Festival (https://britt.org/), which has a summer orchestra and hosts big name touring artists in a beautiful setting. In Jacksonville, often featured on lists of the cutest towns in Oregon, the Britt seats 2,200 and provides a relaxing concert experience with views of mountains and trees and the sunset.
WHAT:
Oregon Shakespeare Festival
WHEN:
Shows run through Oct. 25, with outdoor productions closing Oct. 11.
WHERE:
Ashland, Oregon
TICKETS:
Prices vary.
LEARN MORE:
https://www.osfashland.org/