Are you heading to southern Oregon? Well then, let me tell you about Ashland—a cute and artsy little town might just steal your heart. Though it’s very well known for its yearly Shakespeare festival, there’s so many more fun things to do that I want to tell you about! Let me show you how I spent my perfect 12-hour itinerary there, and how you can too!
Ashland, Oregon 1-Day Itinerary
10:30 AM
Coffee & Brunch at Hither
We kicked off our day at Hither, a cozy little spot that feels like a warm hug in café form. I treated myself to an apricot and fig leaf scone that was oh so buttery and flaky, it practically melted in my mouth. Pair that with an avocado tartine (because who can resist avocado toast, right?) and that was the epitome of a comfort brunch. Add in a few bites of Peter’s biscuit sandwich and I was a happy camper.
If Hither’s buzzing and you’re in need of a Plan B, Mix Bakeshop is just around the corner. Their pastries? Equally as divine—promise!
11:45 AM
Stroll Through Lithia Park
With my belly happy and full, we wandered over to Lithia Park—a 93-acre slice of paradise that feels like your own personal retreat. The park is filled with winding trails, towering trees, and a duck pond straight out of a romance movie. But the hidden gem? The Japanese Garden. It’s tucked away like a secret, full of Asian plants and koi ponds, and it’s so peaceful, you’ll want to stay awhile.
TIP: The Japanese Garden is completely free! If you just want to visit it (and nowhere else in Lithia Park) then park a little closer to the pickleball courts. It’s a little north of the center of the park.
1:45 PM
Explore Downtown Ashland
After a pretty chill morning, I was ready for some (window) shopping therapy in downtown Ashland. This isn’t just any small town—it’s a treasure chest of quirky shops, local artisans, and unique finds. My personal favorite store? Jupiter Row, a place that was born out of a love for everything that makes Ashland special. From handmade treasures to artisan goods it is a little slice of visual lifestyle poetry—where every item tells a story.
TIP: Don’t worry about getting lost—Ashland’s downtown is super walkable, so take your time and explore every nook and cranny!
4:00 PM
Wine Tasting at Weisinger Family Winery
No visit to Ashland is complete without a little wine tasting, right? Just a short drive from downtown, you’ll find Weisinger Family Winery. The tasting room is cozy and welcoming, but the outdoor seating area is where you want to be (weather permitting, of course) I sipped my way through six different wines, falling hard for their bold Malbec while my hubby couldn’t get enough of the Tempranillo.
(If wine tasting sounds a bit intimidating, don’t sweat it! The staff at Weisinger’s are super chill and will help you find your new favorite without any pressure.)
5:45 PM
Dinner at Cocorico
After a day of exploring and sipping, it was time to dive into dinner—and the Southern European restaurant Cocorico was the perfect spot. We started with a watermelon feta salad that was the perfect blend of sweet and savory, followed by charred shishito peppers with just the right amount of heat. But the star of the show? A roasted chicken with peach chutney that was so tender, it practically fell off the bone.
TIP: The inside is cute and cozy, but do yourself a favor and snag a seat on the plant-filled patio. That’s the happening spot!
7:15 PM
Free Green Show at the Oregon Shakespeare Campus
With dinner wrapped up, we strolled over to the Oregon Shakespeare complex for the Green Show. This stage offers free outdoor performances right in the heart of the Oregon Shakespeare Festival campus. And you never know what you might get—live music, dance, theater, or even cultural performances that give you a taste of something new. That evening, we were treated to a performance by Hudost, a modern folk music duo.
It’s a super casual way to soak up some culture without needing a ticket (or breaking the bank). Plus, it’s super family-friendly (including your four-legged family), so it’s perfect whether you’re on a solo adventure or with loved ones.
8:00 PM
See a Live Theater Show
To top off the perfect day, snag seats to one of the shows at the Oregon Shakespeare Festival. Even if you’re not a Shakespeare fan, this is the ultimate bucket list thing to do in Ashland! We caught the show Coriolanus at the Thomas Theatre and were totally impressed with the acting and production.
If you’ve never been to a Shakespeare play before, Ashland is the place to do it—the festival is world-renowned, and there’s something truly special about experiencing it in such an intimate setting.
Make it an Overnighter
Ashland Springs Hotel
If 12 hours just ain’t enough (I totally understand!), then make your visit an overnighter. Staying at the Ashland Springs Hotel is like stepping into a piece of living history with a touch of luxury. This gorgeous hotel, just a quick five-minute stroll from downtown, has been a local landmark since it first opened its doors in 1925. Originally the tallest building between Portland and San Francisco, it’s got that classic, vintage charm but with all the modern comforts you’d want. Imagine relaxing in a beautifully restored room that feels like a step back in time, yet with the convenience of being right in the heart of Ashland’s vibrant scene.
So there you have it—my perfect one-day bucket list itinerary for Ashland, Oregon! It will keep you super busy with eating delicious food, doing a little shopping and getting immersed in some of the artsy culture. Let me know how your day went!
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