The Local's Guide to Ashland

Oregon Shakespeare Festival
Oregon Shakespeare Festival | Oregon Shakespeare Festival
Oregon Shakespeare Festival | Oregon Shakespeare Festival

In no other Oregon town will you uncover such a surplus of wind chimes, books, men with ponytails, and artisanal hula hoops. Ashland, like most prominent Pacific Northwest towns, is best known for its brews and views, but it prides itself on its old-school hippie, Woodstock DNA, which designates it as the most liberal city in Southern Oregon. To fortify that claim, all you need to do is check out the generous amount of gluten-free and grass-fed samples supplied by Ashland’s Co-op; it’s basically the town hall. But the nucleus of Ashland would have to be its curated performing arts scene, which dominates its economy and makes for a national treasure. The Oregon Shakespeare Festival has hosted 20 million visitors since it began with a humble production of Twelfth Night back in 1935. Due to its historical character, Ashland is America’s most comprehensive crack at Elizabethan London (sorry not sorry, New England). Below, we give you a tie-dye sampling of all the pit stops that define this vacationers' oasis.

'Twelfth Night' at Oregon Shakespeare Festival
'Twelfth Night' at Oregon Shakespeare Festival | Jenny Graham/Oregon Shakespeare Festival.

Catch the Shakespeare Festival at the Green Show

The Oregon Shakespeare Festival has performed all of Shakespeare’s plays, depicting each at least 300 times since the festival’s inception. And whether or not you coin Shakespeare (or the Earl of Oxford) as the true author of these works, one must admit that the festival has single-handedly transformed Ashland from small-town America to, well, small-town England in a sense. The Green Show appears six nights a week at 6:45pm sharp from June through October, and it offers festivalgoers and townsfolk alike a culturally enriching encyclopedia of performances, from hands-on science experiments to Native American dance-offs. For free. Every day, there’s something new to experience, and a brand-spanking-new remodel means the Green Show is even more state-of-the-art than before.

Drink in beer history at Caldera Brewing's Tap House

A couple years ago, the internet had a field day with Rogue Brewery’s invention of a Sriracha Hot Stout Beer. Rogue, named after the Rogue Valley, is known as one of Oregon’s staple breweries, and its roots are traced back to a tiny white brick building in the heart of Ashland. The brick-and-mortar is now operated by another brewing pioneer, Caldera Brewing Co., which was the first craft brewery on the West Coast to brew and can their own beer. Over at the Caldera Brewery & Restaurant, a separate facility, you can find Oregon’s largest beer bottle and can display in the restaurant. There’s also a rumor floating around the blogosphere that if you bring a clean mason jar, you can fill up at the bar.

Rouge River
Flickr/Kirsten Comandich

Explore the Rogue River on a scenic drift boat tour

You can’t go anywhere in Oregon without being confronted by its natural beauty; it’s a daily stick-up. Ashland’s specialty? The Rogue River Valley. There are lots of opportunities for catching this basin on a good day, but you’ll want to pay more attention to how you see it. If you’re no stranger to Pirates of the Caribbean at Disneyland and you find getting wet to really grind your gears, you’ll want to take a scenic drift boat trip.

Oregon Vortex
Flickr/Jim Hickcox

Get weird at the Oregon Vortex

Optical illusions or paranormal activity? The world may never know. On the hike to-and-from Ashland, just 30 minutes up the I-5, sits Oregon Vortex, Oregon’s strangest roadside attraction. Think the Rimsky-Korsakoffee House, but in the middle of nowhere. Legend has it that Native Americans thought the land was cursed. As European settlers interacted with the local topography, they found that a gold assay office mysteriously slid down a hill, which baffled their 19th-century European minds. Later, a bunch of ambiguous objects could be seen rolling uphill, and couples would take photographs of themselves only to find their respective heights swapped in the developed picture. Today, you can tour the Oregon Vortex House of Mystery, which will properly spook you based on the given gravity hill.

Antique hunt at one of the most interesting places on the West Coast

Prize Shoppe is no ordinary thrift shop: it’s a vintage haven that specializes in sincerely odd items, such as antique concrete garden animals, old school trophies that your grandpa would have won at the county spelling bee, and first-edition books (you’re in Ashland, after all). Prize has three locations, but Ashland is its only in Oregon -- the other are hotspots in San Francisco and Berkeley, California. To top it off, Prize is located in the historical Enders Building, dating back to 1910 -- like much of the store’s inventory.

Lithia Park
Victoria Ditkovsky/Shutterstock

Get a new perspective amongst the majestic maple trees at Lithia Park

From its Atonement-inspired fountains to the American Planning Association’s 2014 designation of Lithia Park as one of America’s top-10 Great Public Spaces, Lithia Park comes swinging on the national nature scene. As Ashland’s largest park, its 93 acres include numerous hiking trails and abounding nature. Give the Lithia Park Trail a go; it’s short, sweet, and gleefully counted among America’s National Register of Historic Places.

Flaunt your inner (and outer) wino at Liquid Assets

There’s only one bar in Ashland that prioritizes all of the big three: wine, beer, and cocktails. With a rotating menu of over 20 wines by the glass and 250 in the bottle, Liquid Assets is where the vibes remain the most romantic in the middle of the American incarnate of the English countryside. Also, nowhere else in town has as many wine options, so there’s that. The food is Mediterranean inspired, and the cocktails come correct with homemade bitters, freshly squeezed juices, and seasonal infusions. Beer is also well curated: you’ll find Dogfish Head, Russian River, and New Belgium on tap.

Dessert at the Ashland Springs Hotel
Flickr/Al Case

Treat yourself to a damn fine mean at the English Garden

If you like a good riches-to-rags-back-to-riches story, the Ashland Springs Hotel makes for a proper bedtime anecdote. Started as a boutique hotel in 1925, the then-Lithia Springs Hotel was a luxurious link between California and Oregon. The place fell into disrepair in the late 20th century but has since made a full recovery, even going as far as to kick off the farm-to-table culinary movement in the Rogue River Valley. It's also the city’s tallest building, which only bolsters its credibility as a momentous local establishment. Here one can splurge on local craft wine and regional bounty in the scenic on-site English Garden.

Go on a safari-themed spa day

It’s time for you to become formally introduced to the hot stone massage. Or perhaps a salt scrub? At Blue Giraffe Day Spa, a forested retreat located a couple minutes from Downtown Ashland by foot, you’ll entertain much more than a pedi. While getting your wax on, you are complemented with an Elven-savvy, Rivendell-centric view of Ashland Creek. Everybody’s welcome -- especially if you’re the type who enjoys collecting crystals and tarot cards. And don’t let the kitschy, African safari-inspired interior decor throw you off: it'll be one of the most relaxing experiences you can have in Ashland.

Oregon Cabaret Theatre
Oregon Cabaret Theatre

Find out what Dick Hay Pie is. Eat slice after slice.

If you are a human person who has lived on Earth for some time, you’re probably familiar with ice cream cake. In Ashland, ice cream cake has some stiff competition in the form of Dick Hay Pie, which is “ice cream pie.” It’s a splash of vanilla ice cream, peanut butter (I know), and a thick drizzle of hot fudge. It’s served at the Oregon Cabaret Theatre, which brings us to...

Oregon Cabaret Theatre
Oregon Cabaret Theatre

Spend the evening at the Oregon Cabaret Theatre

When you’re ready to bump yourself up a few centuries from Elizabethan England, Ashland holds Oregon’s most soulful rendition of the 1930s. The Oregon Cabaret Theatre often blends its shows with its audience, offering interactive performances that can get a bit gritty -- even for an establishment sitting in an old Baptist church. But if you have any soft spot for Liza Minnelli, you won’t want to miss one of these acts in action.

Pace yourself on the First Friday Artwalk

For whatever reason, cities usually showcase the majority of their artists within their industrial epicenters. And for whatever reason, a small town like Ashland is no different. From 5pm to 8pm, you can hike the First Friday Artwalk. It features an array of galleries throughout the Historical Downtown and Railroad Districts, featuring opening receptions for fresh monthly art exhibits. One of First Friday’s most popular hosts is Ashland Art Works, a neighborhood confederation of local artisans, jewelers, and ceramicists. Expect paint, booze, and history -- and be sure to wear sneakers.

Lithia Park Waterfalls
Flickr/Al Case

Go searching for Ashland's secret waterfall

There are many hidden gems nestled deep within the Oredson-Todd Woods. Sprawling with 7 miles of various trails and an elevation of 900 feet, a simple hike will unearth Oregon’s only native orchid, the rich magenta calypso bulbosa, which grows naturally along this terrain and vaguely resembles a dragon’s head. If you’re looking for waterworks and a slice of the Garden of Eden, you’ll want to follow the Oredson-Todd Woods Trail, which will take you to an ethereal waterfall of biblical proportions.

Be the next big playwright

No festival will ever quite meet the weight of the Oregon Shakespeare Festival in terms of feeding the local economy, but that doesn’t mean other festivals can’t hold their own. The Ashland New Plays Festival, unlike the Shakespeare Festival, gives contemporary playwrights the mic. During the New Plays Festival flagship events in mid-October, four plays are chosen from hundreds of national submissions to come alive each fall. Submit your play here.

Alchemy Restaurant and Bar
Alchemy Restaurant and Bar

Drink like the Portland hipster you are at Alchemy

Alchemy Restaurant and Bar has been a big hit since exploding onto the local cocktail scene in 2013 as the tail of the historic 1883 Winchester Inn. And it’s easy to see why: In 2015, it was named to the OpenTable Diners' Top 100 Best Restaurants for Foodies in America. This affirmation comes with the joint only being two years out of the gates. Alchemy incorporates many of the same elements that make upscale, modern Portland cocktail bars impress: hundreds of carefully curated spirits, a Multnomah Whiskey Library aesthetic, a daring, seasoned menu (seared foie gras), and even a grandiloquent website.

Douse yourself in the visual arts at the Schneider Museum

Another perk to being a college town? A community-wide focus on the arts. The Schneider Museum of Art, part of Southern Oregon University, was built by a Portland-based architect and opened in 1986. Ever since, it has harvested a selection of exhibitions focused on historical perspectives of art (fitting for Shakespearetown, USA) and progressive contemporary art. Currently, it offers four separate galleries, each zeroing in on influential contemporary West Coast artists.

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Jack Rushall is a Portland-based freelance writer for Thrillist, MUNCHIES and The Washington Post. He likes to open windows. You can follow him on Instagram @fromrushallwlove, or on Twitter @JackRushall.