Oregon is a place that welcomes the weird, and there’s a little town in the southern part of the state that truly marches to a beat all its own. Known for its Shakespeare festival and hippie vibes, Ashland is an endearing little iconoclast of a place. Perhaps the most offbeat, eccentric town in Oregon, Ashland is an absolute delight. And once you get a taste of this weird and wonderful little town, you may never want to leave.
Located in Southern Oregon’s resplendent Rogue Valley, Ashland is a place of breathtaking natural beauty and a free-spirited community.
Jeff Hitchcock/Flickr One of Oregon’s smaller towns, Ashland has a population of just over 21,000.
The town is most known for its arts scene.
Visitor7/Wikipedia The eponymous Ashland Independent Film Festival is like a mini Sundance, but with total Oregon vibes.
And The Oregon Shakespeare Festival really is the heart and soul of the community.
perrin w/TripAdvisor Founded in 1935, this live theatre venue is straight out of the 1600s, complete with the troupe’s iconic outdoor Allen Elizabethan Theatre, which opens in early June and runs through mid-October.
And the theatrics continue in town, where you’ll find a variety of shops with tongue-and-cheek names that would make The Bard proud.
K. Kendall/Flickr
Renaissance Rose is one of the most eccentric spots in town, selling masks, costumes, and all things vintage. Everything about this place is extra, in the best possible way.
Renaissance Rose You can pick up some masks for your own rendition of A Midsummer Night’s Dream.
The Ashland Library is one of the town’s most gorgeous buildings. Its outdoor green space is an inviting little oasis where you’ll generally find folks reading, sketching, or strumming a guitar.
Krister Axel/Google Local
And the restaurants downtown definitely speak to Ashland’s laidback attitude. Morning Glory is the place to go for brunch in Ashland; it’s a cozy little restaurant dishing up big plates of comfort food.
Soozesun/TripAdvisor
Oregon is big with the whole “farmcore” movement, proudly supporting local farmers and artisans. And this is epitomized with Ashland Food Co-op, the town’s beloved organic, community-owned grocery store.
Ashland Food Co-op/Facebook
This connection with the earth really is part of Ashland’s collective identity. Lithia Park is the city’s crown jewel; it’s 93 acres of fairy-tale forests around Ashland Creek, stretching from the town plaza to Mount Ashland.
Mitch Diamond/Photodisc Collection via Getty Images
And if you want to really experience Ashland’s natural splendor, head out to Willow-Witt Ranch.
Willow-Witt Ranch
Willow-Witt Ranch is a 445-acre organic farm in Southern Oregon’s high country, where you can come and enjoy a magical and memorable experience on a real, working ranch.
Willow-Witt Ranch The ranch offers several different camping experiences, but staying overnight in a furnished tent surrounded by Southern Oregon’s expanse of farmland and forests sounds particularly perfect.
You can really get in touch with nature, and go backpacking with the farm’s friendly goats.
Willow-Witt Ranch
Other unique accommodations in Ashland can be found at Wellsprings Spa. This natural hot springs destination has an organic garden, meditation temples, and myriad camping options, including tipis, domes, and bell tents.
WellSprings Ashland/Facebook
The main attraction here, however, is the Olympic-sized swimming pool, which receives 80,000 gallons a day of naturally alkaline, mineral water, and is thought to have therapeutic properties.
WellSprings Ashland/Facebook
In fact, the warm waters in the Jackson Hot Springs/Bear Creek area have long been believed to possess healing powers; these waters were even used as ceremonial and birthing sites by Native American tribes.
sinatrajr74/TripAdvisor
In town, you’ll even find Ashland’s life-giving, lithium-loaded waters flowing from a public fountain.
K. Kendall/Flickr
While the jury is out on the actual powers of these waters, that’s really beside the point.
K. Kendall/Flickr
Because after spending time in the delightful, eccentric little town of Ashland, you’ll want to drink the water, too.
Willow-Witt Farm
Ashland really is the perfect slice of small town life in Oregon, in all its weird and wonderful glory. If you’re feeling drawn to small-town life in Oregon, be sure to check out these 11 charming cities.
Jeff Hitchcock/Flickr
One of Oregon’s smaller towns, Ashland has a population of just over 21,000.
Visitor7/Wikipedia
The eponymous Ashland Independent Film Festival is like a mini Sundance, but with total Oregon vibes.
perrin w/TripAdvisor
Founded in 1935, this live theatre venue is straight out of the 1600s, complete with the troupe’s iconic outdoor Allen Elizabethan Theatre, which opens in early June and runs through mid-October.
K. Kendall/Flickr
Renaissance Rose
You can pick up some masks for your own rendition of A Midsummer Night’s Dream.
Krister Axel/Google Local
Soozesun/TripAdvisor
Ashland Food Co-op/Facebook
Mitch Diamond/Photodisc Collection via Getty Images
Willow-Witt Ranch
The ranch offers several different camping experiences, but staying overnight in a furnished tent surrounded by Southern Oregon’s expanse of farmland and forests sounds particularly perfect.
WellSprings Ashland/Facebook
sinatrajr74/TripAdvisor
Willow-Witt Farm
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Address: Ashland, OR 97520, USA
