Ashland, Oregon, is one of those towns that feels like it was designed for lingering—whether you’re soaking in the springs, sipping local wine, or strolling through leafy parks. Found in Southern Oregon’s Rogue Valley, it’s best known for its Shakespeare Festival, but there’s so much more here: fabulous dining, boutique shopping, natural beauty, and world-class hospitality. I spent 24 hours, a perfect day in Ashland, OR, and left already planning my return.
Here’s what I did.
Morning Magic at Lithia Springs Resort
My home base for this trip was Lithia Springs Resort, a serene retreat renowned for its mineral-rich waters, lush gardens, and luxurious accommodations. The rooms are spacious and inviting, featuring soaking tubs that allow for enjoying the spring water in complete privacy.
If you’re traveling with pets, the resort goes above and beyond—offering thoughtful extras like local vet, grooming, and dog park info to make your pup’s stay as special as yours, and fancy treats.
I started the day with their breakfast buffet, which offers everything from eggs and fruit to gourmet yogurt, steel-cut oats, biscuits and gravy, and the real star—the scones. (Do not miss them!)
After breakfast, I wandered the property snapping photos of the lush flowers, admired the outdoor pool, and took a moment to sit in one of the many inviting garden nooks.
Strolling Through Lithia Park
Just a few minutes from the resort is Lithia Park, a green oasis with over 90 acres of beauty. Expect fresh air, meandering trails, shady trees, and often the sound of talented local musicians adding a soundtrack to your walk. I got lucky and experienced the sounds of cellist Daniel Sperry not far from the park entrance.
The Japanese Garden is a highlight, complete with a koi pond and an atmosphere so serene it feels like snuggling with nature. This place is seriously good for both body and soul.
Lunch by the Creek
When hunger struck, the group I was traveling with headed to Greenleaf Restaurant, where outdoor seating made the meal even more memorable. Their breakfast, lunch, and dinner menus shine with fresh, flavorful dishes, many of which are PNW-inspired.
I loved the salad and sandwich options (hello, wonderful-sounding Greenleaf Chicken Piccata sandwich), but the Mediterranean quesadilla (roasted tomatoes, spinach, feta, and avocado) won me over. Pair it with a crisp local wine or refreshing iced tea and enjoy the relaxing creekside views and people-watching.
Afternoon Shopping & Sipping
Downtown Ashland is a treasure trove for shoppers. Whether you’re into gourmet kitchen accessories, whimsical décor, stylish clothing, or global-inspired housewares, you’ll find something to tempt you. A few of my faves were Gypsy Road Studio, The Culinarium, and The Drift Collective.
The Websters is a shop for fiber enthusiasts, and just peeking inside made me want to start a new hobby. I loved the Little Free Fibrary Box in front of the store where you can swap yarns with other crafters. What a clever idea!
Book lovers shouldn’t miss the beloved local bookstore—Bloomsbury Books. I loved wandering through its shelves and browsing the gift items. If you’re hungry or thirsty, a lovely oasis awaits you upstairs in the café, with a most decadent-looking quiche.
Need a caffeine fix? Pop into the nearly 20-year-old town staple, Mix Bakeshop, for expertly crafted coffee, tea, and pastries. The cheesy herb scone I grabbed for later is still haunting my taste buds in the best possible way.
No visit to the Rogue Valley is complete without a wine tasting experience. With nearly 150 vineyards and tasting rooms to choose from, you’re spoiled for choice.
Many wineries are just a short drive from town, making Ashland an excellent home base for wine lovers. I can attest and give thumbs up to Red Lily, Weisinger, and Hummingbird Estate.
The Historic Ashland Springs Hotel
Even if you’re not staying overnight, stop into the Ashland Springs Hotel downtown. This landmark property, over 100 years old, blends vintage elegance with modern comforts. The lobby is breathtaking—think classic architecture and old-world charm—and their onsite restaurant, Lark, serves chef-driven farm-to-table meals that make for a memorable dining experience.
Evening Theater
Ashland is famous for its Oregon Shakespeare Festival, a tradition that has been going strong for over 90 years, with productions running from March through late October. Don’t worry if Shakespeare feels intimidating—this award-winning festival has a way of making everyone a fan.
I saw The Importance of Being Earnest at the intimate Angus Bowmer Theatre, and let me tell you: the set, the talent, the energy—everything was exceptional. We laughed until our sides hurt, and I walked away with a new appreciation for the caliber of performances that Ashland consistently delivers.
Pro Tip: Restrooms are on the lower level, so plan accordingly. Additionally, all seats offer great views, so consider saving a few bucks by purchasing seats not located near the front or middle.
Dinner to Remember
For dinner, we couldn’t resist Bar Juillet, an urban, minimalist dinner spot that’s perfect for sharing clean cuisine plates, sipping sensational wines, and indulging in upscale cocktails and zero-proof options. Highlights of the night included the fried chicken, whipped ricotta focaccia, burrata with peaches, and a refreshing watermelon ricotta mint salad—great for passing around the table family-style.
It was the perfect way to cap off a day filled with indulgence, beauty, and cultural treasures.
Why Ashland Belongs on Your Travel List
In just 24 hours, Ashland delivered gourmet dining, world-class theater, gorgeous gardens, historic charm, boutique shopping, and incredible hospitality. Whether you come for the Shakespeare Festival, the wineries, or to soak in the beauty of the Rogue Valley, Ashland has a way of stealing your heart.
It certainly stole mine—I can’t wait to return.
To learn more about Ashland or order a visitor’s guide, click here.
Thanks to Travel Medford and Visit Ashland Oregon for hosting my familiarization trip after the Travel & Words conference. As always, reviews and opinions are 100% mine and unbiased.
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