There is a lot to love about Southern Oregon. From wine tasting to shows at the Oregon Shakespeare Festival to extraordinary culinary adventures, this one-of-a-kind region has something for everyone. Read on to discover seven of the best things to do in Ashland, Oregon. Afterward, if you are looking for more ways to spend your time, download our free Ashland Vacation Guide! It is full of recommendations on parks, restaurants, entertainment, and more.

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7 of the Best Things to Do in Ashland, Oregon

1. Take an Early Morning Hike

Ashland, Oregon, is home to several unique hiking trails, and when you stay at Country Willows B&B Inn, you won’t need to travel far to find two of them. Starting at our inn, you can amble your way up the meadow path to the Irrigation Canal Trail. This trail connects to the Ashland Trail System, where you can find one of Southern Oregon’s most beautiful waterfalls! With songbirds, sunshine, and towering trees, an early morning hike is one of the best ways to appreciate the region’s natural beauty. (For more information on trails that are convenient to Country Willows, read our blog on hiking in Ashland)

2. Enjoy a Day On the Water

Ashland’s waterways beckon all to explore! Swimming at the Ashland Creek in Lithia Park and rafting down the Rogue River are both popular ways to cool off during the summer. Noah’s River Adventures or Momentum River Expeditions are two excellent local rafting guides. Whether your ideal trip is an easy float, basking in the sun or a wild ride on the white water, Ashland has it all.

3. Delve Into the Arts at First Friday Art Walk

Whether you are an artist, a collector, or looking for the perfect Southern Oregon souvenir, you don’t want to miss First Friday Art Walks. This special art even is on the first Friday of the month. It is a wonderful way to catch a glimpse into superb artisan craftsmanship. With featured artists in attendance, onsite demonstrations, and refreshments, you’ll revel in this night out on the town!

4. Shop the Local Markets

Ashland is one of the best places in the region to find fresh and local produce throughout the year. If you are looking to bring home a taste of Southern Oregon with you, then make a trip to The Ashland’s Grower’s Market. Here, you will find organic fruit or vegetables, Rogue Valley plants, homemade jams, raw honey, and more!

Another unique market is The Lithia Artisans Market. This artistic event finds favor with all seeking to bring home handcrafted jewelry, art, and clothing. It is every weekend from spring through fall!

5. Expand Your Theatrical Horizons

If you are planning a trip to Ashland, Oregon, chances are that you are coming for the Oregon Shakespeare Festival. During your trip, remember to enjoy all the offstage events that the festival offers. Extra events at the Oregon Shakespeare Festival include the Green Show and Noon Talks. The Green Show offers free music throughout festival season, featuring everything from soulful jazz to bluegrass to dance performances. Noon Talks are a great way to deepen your theater experience. Meet scholars and theatre artists from around the country at this educational event!

6. Embark on a Culinary Adventure

No trip to Ashland is complete without diving into the culinary arts scene. Whether you are craving savory charcuterie or something on the sweeter side, like artisan chocolates, you will find it all here. In addition, the city is home to many outstanding wineries and vineyards. For a vacation that you won’t soon forget, we recommend taking a winery tour. Don’t forget to stop by a local bakery for a sweet treat afterward!

7. Relax

With all the conveniences of a bed and breakfast and the luxuries of a boutique inn, there is no better place to relax than Country Willows B&B Inn. Nestled along Ashland’s beautiful countryside, just minutes away from downtown, our guests enjoy the best of what the area offers. Take advantage of the many restful spots located on our property, including a heated outdoor pool, double front porches, elegant rooms with working fireplaces, and more.

We also offer daily farm-to-table breakfast, hot tea throughout the day, and many other perks that will help you unwind and return home feeling completely refreshed!

If you are ready to plan your next vacation, check our current specials and book your stay. We can’t wait to host you at Country Willows B&B Inn!