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Kirk Drake
May 19, 2024 | Kirk Drake

Ashland Oregon Afternoon Itenerary

An Unconventional Afternoon in Ashland, Oregon

What do you get when you mix juicy burgers, serene gardens, bold wines, and a touch of Shakespearean drama? A great list of things to do in Ashland, Oregon that’s anything but ordinary. Buckle up, Enlightened Zaggers, because we’re taking you on a whirlwind tour that defies all expectations.ashland oregon wine tasting walkable

We kicked off our adventure with a burger at Flip, downtown’s hidden gem that laughs in the face of boring fast food. This isn’t your average patty—it’s a mouthwatering masterpiece that’s worth every delicious bite. And don’t get us started on the fries. Flip sets the bar high, and we’re just getting started.

Next, we took a leisurely, unpretentious stroll to Lithia Park. No need for maps or guides; just follow the scent of tranquility to the Japanese Gardens. These gardens are a serene escape from the mundane, with koi ponds and zen vibes that make you forget you’re just blocks from civilization.

Feeling zen yet? Time to shake things up with a pre-show wine tasting at Resistance Wine Company. We’re not your typical winery—we’re the rebels of the vine. Sip on our award-winning 2018 Syrah and discover flavors that laugh in the face of convention. It’s wine tasting, but not as you know it.

With a pleasant buzz and a newfound appreciation for the unconventional, we wandered over to the OSF Courtyard for a free afternoon show. Shakespeare outdoors? Yes, please. It’s lively, it’s engaging, and it’s a cultural experience that’s refreshingly different from your standard stuffy theater.

Ashland Oregon Group Wine Tasting

Dinner time rolled around, and we made our way to Peerless Restaurant. This place is the culinary equivalent of a mic drop. Every dish is a statement, every bite a revelation. From the appetizers to the main courses, Peerless doesn’t just serve food—it serves unforgettable experiences.

To cap off our day, we indulged in a soak at Chozu Bath and Tea Gardens. This isn’t your grandma’s spa day—it’s a sanctuary of calm that washes away the day’s adventures with warm, mineral-rich waters. Total relaxation achieved.

Finally, we wound down at the Swank House, Ashland’s answer to cookie-cutter accommodations. This charming bed and breakfast is all about comfort with a twist, the perfect end to a day that’s been anything but typical.

So, there you have it. A day in Ashland that breaks all the rules, just the way we like it. From Flip’s killer burgers to Resistance Wine Company’s audacious flavors, every moment defies the ordinary. Ashland, Oregon—where the unexpected is the norm, and every experience is a new adventure.



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