Ashland is home to countless amazing businesses and the award-winning Oregon Shakespeare Festival. This destination deserves more appreciation, especially at a time when independent shops, restaurants, and theatre companies need additional support.
Tucked away in the forests of Oregon is one of the most underrated destinations in the world. The lovely town of Ashland, Oregon is rarely featured in major travel publications. Yet it is a gorgeous world of its own, comprising a distinct Shakespearean and LGBTQ+ friendly culture, lots of sustainably delicious food, and fairy tale-esque forests. Its claim to international fame is the Oregon Shakespeare Festival (OSF), but still few people have heard of it.
Having visited Ashland several times, I fall into a wistful routine every time I go back. The first thing I do is stop by all my favorite shops on Main Street and in the surrounding area. I lose myself in a cacophony of fairycore, vintage, and neoteric clothes, home goods, and trinkets from the likes of Thread Hysteria, Book Exchange, and Rare Earth. Among Ashland’s boutique shops, the department store Paddington Station is the crown jewel.
Paddington Station first opened in 1973 and has since expanded to include the sister stores Paddington Jewel Box and Inspired by Oregon. Vice president and product manager Kelly Jean Hammond’s parents bought the business in 1993.
“When the store opened,” says Hammond, “Ashland was even more of an artsy hamlet than it is now! Back then, the name Paddington Station would have been synonymous with the other uniquely British-sounding hotspots in town. While old haunts that no longer remain had names like ‘The Underground Deli’ and ‘Tin Pan Alley,’ English-y landmarks like Bloomsbury Books, The Black Sheep, and of course, [OSF], still define our vibrant downtown.”
Paddington sells everything from adorably decorated dishware, to jewelry with real pressed flowers, to the best floral-patterned clothing, to an impressive selection of pronoun pins with options you don’t see too often, like “she/they” or “I respond to all pronouns.”
This is characteristic of Ashland being a center of LGBTQ+ pride and the land of gender-neutral bathrooms—restaurant owners seem to have painted over old bathroom signs in the most creative ways possible. The décor compliments Ashland’s equally creative and comforting cuisine.
Greenleaf Restaurant might be called the most reliable restaurant in Ashland, an essential link in the chain of Main Street: Around a dozen businesses lined up next to each other all share a back patio overlooking Ashland Creek, just a stone’s throw away from the OSF theatres. Having Greenleaf’s chicken alfredo (still one of the best I’ve ever had), sitting in the sun, admiring the flora and listening to the creek, all make for a perfect afternoon.
After maybe some more shopping and changing into evening clothes, I inevitably end up back on Main Street for dinner at Oberon’s Restaurant & Bar or Brickroom Gathering House before the evening show. At Brickroom, classy geometric designs meet a rustic industrial interior, where craft cocktails and classic American dishes with a creative spin are served—if you go there, order a plate of Filthy Fries for me.
Oberon’s looks like the place where Shakespeare’s fairies go after they are done pranking foolish morals, and proclaims itself “Ashland’s most Ashlandiest spot.” In addition to its whimsical interior, it is perfect for cocktail lovers, boasting a variety of homemade components. According to owner Andy Card, this includes infusing syrups and spirits with ingredients such as organic lavender, chamomile, earl gray, and beeswax.
“My favorite is infusing organic strawberries with Aperol over a few days and making strawberry Aperol spritzes for summertime,” says Card. “For every cocktail menu, I bring in a few new infusions.”
After one cocktail (because I will fall asleep during the play if I have more), it’s off to the theatre! 2023 was a particularly amazing year for OSF. The “Season of Love” comprised the best line-up of shows out of the four times I have visited Ashland. This included a performance of Romeo and Juliet more impactful than any I have ever seen before, a maudlin and blues-y rendition of Twelfth Night, a production of Rent reminiscent of its original Broadway run, and a version of The Three Musketeers that I, with the deepest regrets, did not get to see.
In her message featured in several of the shows’ programs, former OSF artistic director Nataki Garrett describes how these shows depict everything from “the love and commitment between comrades” to “the complexity and all-consuming pain of unrequited love,” and “[how] the bonds of family and friendship—and the power of music and art—are the lights that guide us through.”
“This season is our love letter to love,” says Garrett. “It’s our love letter to our incredible artists and the work they create and it’s our love letter to you, our beloved audience, both new and traditional, young and old, from across the country and around the world.”
Although it was a great year for the art, it wasn’t so much for the money. Ahead of the 2023 season, OSF admin sent out an email to members advertising the “The Show Must Go On” campaign. The email expressed an urgent need to raise $2.5 million to launch the season, due to a financial crisis caused by inflation and the lingering effects of the COVID-19 pandemic. This is symptomatic of independent theater in general struggling since 2020.
The morning after a show, I end up at Morning Glory Café for lemon ricotta French toast in a quirky white-picket-fence setting. Maybe after you have breakfast you will do the whole thing all over again, with a different combination of restaurants and shops. You might also try a matinee show, and then embark upon a small bar crawl in the evening. Bar Juillet is another location for cocktails and wines standing alongside Oberon’s and Brickroom.
If you require an alcohol-free evening, Elder Apothecary is a soothing stop at the end of the day, where you can enjoy an herbal latte and a vegan cupcake. “Ashland is the perfect location for an herbal apothecary because it is well located in an area of farmers that grow organic medicinal herbs,” says co-owner Willow Holloway. Elder opened in 2020 and provides locals and visitors with a store of organic health and beauty products, as well as classes and performances.
What else is there to do before you leave Ashland? Go for a walk in the park. Lithia Park is an impossibly tranquil setting of drifting greenery and placid ponds. A cool summer morning in Ashland is the perfect time for an ethereal stroll.
I never tire of Ashland's beauty, or the way it encourages me to discover something new about anything from As You Like It to matcha lattes. “Ashland remains a one-of-a-kind community where love prevails, art reigns supreme, and small businesses thrive,” says Hammond. “Ashland's appreciation for the arts, support of self-expression, and love for fellow man is what makes me proud to be part of this community.”
For 2024, OSF’s traditional Shakespearean program includes Macbeth, Coriolanus, and Much Ado About Nothing. There will also be several meta-textual plays: Born with Teeth, depicting the rivalry between Shakespeare and Kit Marlowe, as well as Shakespeare and the Alchemy of Gender and Virgins to Villains: My Journey with Shakespeare’s Women, both commenting upon gender in Shakespeare.
OSF’s 2024 season will hopefully prove to be more stable after last year’s financial crisis. And hopefully, more travelers will discover and come to appreciate Ashland’s magic in the future.
You can read my full reviews of OSF’s 2023 productions of Romeo and Juliet, Twelfth Night, and Rent via my Substack.
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