Where Shakespeare meets wine country and outdoor adventure, Ashland packs an incredible amount into one charming Southern Oregon getaway. Here’s how to experience the best of it in three days.
By Teddy Danielson
So far as the United States goes, Ashland, Oregon is way up at the top of my list of favorite cities. While it’s technically a “city”, it’s got the warmth and community spirit of a small town. The people are welcoming, everyone waves, and so many of the businesses are locally owned.
Tucked into Southern Oregon between the Siskiyou and Cascade mountain ranges, Ashland packs an incredible amount into just a few square miles. It’s best known as the home of the world-renowned Oregon Shakespeare Festival, but that’s just the tip of the iceberg. It’s jam-packed with opportunities for wine tasting, hiking, white water rafting, and indulging your inner foodie. And, so far as looks go, it’s one of the prettiest downtowns in the Pacific Northwest.
While Ashland is worth visiting year-round, I highly recommend planning your trip between March and October. That’s when the Oregon Shakespeare Festival is in full swing, outdoor concerts and community events fill the calendar, wineries host live music, and the surrounding mountains and rivers are perfect for adventure.
Let’s dive in, shall we?
Lodging + Transportation
Before I get you hyped up about all of the wonderful things to do in Ashland, let’s get you settled into some lodgings, shall we? Here are just a few of my favorite options:
- For a splurge: Ashland Creek Inn is, in my opinion, the best (and most romantic) hotel in town. Its creekside setting and proximity to Lithia Park make it highly desirable. With just 10 distinctive suites, each with its own private entrance and deck overlooking the creek, you’ll want to make your reservation well in advance.
- Middle of the Road: The Winchester Inn’s historic rooms are well-appointed, and the hotel is centrally located. It’s also home to two of Ashland’s most awarded fine-dining restaurants, Alchemy and Chateaubriand 36, and boasts a pretty spectacular complimentary breakfast.
- Budget-friendly: Just outside of town, Green Springs Inn is a sweet little getaway featuring a lodge with guestrooms as well as private cabins for family stays. It’s a budget-friendly option that doesn’t cut corners.
Transportation
You will definitely want a car when visiting Ashland, as a fair portion of its draw is found in the nature surrounding the town. So, rent a car, or arrive in your own, to experience the magic of Southern Oregon in full.
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Day 1
Morning
What’s that? Coffee and adventure calling? Here we go! Start your first day in Ashland with coffee and a pastry at Bloomsbury Books. This cozy bookstore/cafe is a goldmine for readers, especially for those who appreciate contemporary fiction. The coffee’s great. The pastries are top-notch, and it’s a great place to browse as you sip and savor a light breakfast before setting off on a hike.
The hills surrounding Ashland have no shortage of hiking trails, but my favorite is Grizzly Peak. About a 30-minute drive from downtown, this 5-mile hike has some incline, but it’s quite manageable. And the panoramic views of the Rogue Valley, Mount Shasta, and the Cascade Range from the top are hard to beat.
Afternoon
On your drive back to town, get excited about brunch at La Baguette Music Cafe. La Baguette is Ashland’s longest-standing family bakery, and I am a BIG fan of their jalapeno-cheddar stuffed bagel. Their almond poppyseed bearclaw is pretty amazing, too. If you’re around on a Wednesday or Saturday, this sweet little Ashland hang features live music from 10:30-12:30.
After brunch, it’s time to do a little in-town exploration. Start at Lithia Park. This central gathering place is comprised of 100 acres of gorgeous greenspace. It’s got pickleball courts, volleyball courts, duck ponds, a playground, a swimming reservoir, and more. The Japanese gardens are SO peaceful. A great spot to sit quietly and clear your mind. Oh, and you have to stop to take a drink at the Lithia Fountain. It’s a time-honored tradition with a special surprise. You’ll see!
Once you’ve gotten your fill of the park, take some time to explore Ashland’s quaint downtown area right next door. Here, you’ll find over 30 art galleries and studios and a wide area of shops. I am particularly fond of Ashland Art Works. This art collective showcases a rotating collection of works from 16 local artists in various mediums. It’s a fabulous way to get to know local talent.
Aside from the art, Ashland is home to many a cute shop. Pop into the Webster (hands down my favorite ever yarn store) to get inspired for your next project. Then, check out True Lavender Collective for locally crafted lavender products for the home, your body, your taste buds, and more.
Evening
When evening rolls around, you might want to consider seeking out a Shakespeare play. As I mentioned earlier in this article, Ashland is perhaps most famous for being the hub of the Oregon Shakespeare Festival. So, from March through October, the town is brimming with plays on plays on plays on three main stages. There’s no shortage of shows, so feel free to sit for one before or after dinner at the Brickroom.
The Brickroom was the first restaurant I visited when I came into Ashland. The vibe is modern and, well, cool with its brick-lined walls and clean lines. And the small plates and cocktails are delish. Grab an order of dirty fries and a Mezcal cocktail and see where the night takes you.
Day 2
Morning
Today’s another busy day with kayaking, wine tasting, and music in the park. I’m going to start you off with breakfast at Morning Glory Cafe. This funky, colorful, award-winning eatery is a favorite for locals and visitors alike. It’s usually pretty bustling, so you may need to wait for a table, but the crepes and omelets are more than worth it. I also really like the sourdough blueberry pancakes.
After you’ve licked your plate clean, get yourself over to Emigrant Lake. It’s a little less than a 15-minute drive, and it’s a tranquil spot to launch a kayak. You can rent a kayak (or a paddleboard) on-site, so it’s easy to get out on the water fast. Take in the views of the surrounding hills as you paddle off those Chilequiles. Please note that this activity is best kept for the morning hours, as the wind picks up in the afternoon, making the lake choppy.
Afternoon
Dry off and drive on back to town for a well-earned lunch at Skout Taphouse & Provisions. This popular open-air hang serves up a plethora of domestic and imported brews and some seriously crave-worthy fish and chips as well as some healthier options (I like “The Bowl”).
Skout is right next door to Lithia Park, so linger over lunch and take in the views. You earned it.
Next up? Wine tasting! Grab a bike (or an e-bike) from Ashland Mountain Adventures and set off to tour some of Ashland’s best wineries. In case you didn’t know, Ashland is a major wino hot spot. It’s particularly well known for its Pinot Noirs, but that’s just the tip of the iceberg. Resistance Wine Company has some awesome wine-tasting trails that cater to all levels of endurance, posted on their site.
For beginners, I suggest their “Leisurely Vineyards Tour”, which will take you to Long Walk Vineyards, Resistance Wine Company, and Weisinger’s Winery. For more ambitious bicyclists, check out their other trail guides. Many of Ashland’s wineries host events throughout the month, such as live music, food truck nights, and so on. So be sure to look at their calendars if you have a few extra days in town.
Evening
Ok so you had a big lunch, AND you went wine tasting. You might not be hungry for dinner, but, regardless, your next stop should be Lithia Park for an evening of music, food trucks, and local vendors. Between the city’s Summer Sounds Concert Series and Ashland Folk Collective, these events happen regularly, and they’re a great way to mingle with the community.
Energy levels pending, I highly suggest you try to make it to a show at Oregon Cabaret Theatre. Performances usually start at 8 pm, so you’ll have plenty of time at the park before cruising over. The Cabaret Theatre puts on Broadway-quality shows in a small theatre in the heart of town. This year, they’re doing a spin on Dracula, Chicago, Robin Hood, and more. You can have dinner at the theatre, but I’m guessing you’re tapped out on yummy food at this point!
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Day 3
Morning
Good morning and welcome to your last action-packed day in Ashland, Oregon. Fuel up at my favorite food truck, Good Morning Breakfast & Brunch. You can track their location here. I think their Chilequiles take the cake, but their breakfast tacos are pretty stellar as well. Make sure to get there early; you’ve got places to be at 9 am!
Done with breakfast? Great! Head on over to Noah’s River Adventures. You’re going white water rafting. Noah’s offers a wide variety of rafting trips, including full-day and multi-day adventures, but I suggest their half-day Rogue River trip. Suit up (they’ll provide everything you need), and let the knowledgeable guides take you on a well-rounded trip through exciting rapids and peaceful float sections. Don’t forget to look around. The views of the Rogue River are just as memorable as the whitewater itself, with forested hillsides, rocky cliffs, and plenty of opportunities to spot local wildlife.
Afternoon
For lunch, stop by Sammich to pick up a mouthwatering, hulking sub. They have a wide selection of hot and cold subs. In the summer, I’m an Ashlyn girl (It’s got turkey and cranberry!). In the colder months, the tuna melt is to die for. Enjoy yours in-house or take it to go for a picnic in Lithia Park.
For the rest of the afternoon, I suggest relaxing in town. Shop for souvenirs or, better yet, grab a game (or five) of pickleball at the courts in the Park. This is also an opportunity to explore Lithia Park a bit more thoroughly. Spend a little extra time in the Japanese gardens and make friends with the ducks.
Evening
As afternoon fades into evening, get yourself a little dolled up and take a seat at Good Juice. This cute, central wine and sake shop offers nibbles and tasting flights. It’s a great way to sample a variety of local wines from different vineyards and a fabulous way to kick off your last evening in town.
If your last evening happens to fall on a First Friday (and I hope it does!), have a wander around town, popping into local galleries that stay open late for Ashland’s First Friday Art Walk before heading to dinner.
Ashland has many fabulous restaurants, but Cocorico is at the top of my list. With fabulous cocktails, fabulous wine, and a thoughtfully crafted, seasonal menu of modern Mediterranean dishes, it’s a must. I like going with friends and eating tapas-style from their starters menu (LOVE the watermelon + feta dish lately), but their entrees are incredible as well.
The Takeaway
With three action-packed, foodie-approved days in Ashland under your belt, I’m pretty sure you’ll understand why so many people fall in love with this little Southern Oregon town. Whether you came for the Shakespeare Festival, the outdoor adventures, the incredible food and wine, or simply a relaxing weekend away, Ashland has a way of making you want to stay just a little longer. And if you ask me, that’s the mark of a truly great destination.
Need more 3-day itinerary inspiration? Check out our Travel Guides for fabulous itineraries in some of the world’s most charming and beautiful cities.
