The Best Things to Do Near Downtown Ashland, OR

Take a trip to the historic heart of Ashland, where boutique shops line the streets and the smells of farm-to-table restaurants waft through the air. Downtown Ashland is home to a variety museums, art galleries, and of course, the Oregon Shakespeare Festival theaters! Whether you are planning a weekend getaway or your next vacation, there are plenty of things to do here to keep you busy for days!

Below, we’ve provided a comprehensive guide of the best things to do around downtown Ashland, OR, but if you are searching for more, simply download our free Ashland Vacation Guide. Our guide includes over 100 recommendations on the area’s top attractions, outdoor recreation, restaurants, entertainment, and more!

Your Guide to Downtown Ashland, OR

Art & History

Many know downtown Ashland as home to the Oregon Shakespeare Festival, but this fantastic theatrical event is just the beginning of what downtown Ashland offers. Elevate your downtown trip with a visit to these art galleries and museums.

  • Ashland Art Center offers classes and workshops in drawing, painting, printmaking, ceramics, and more.
  • Art & Soul Gallery features fine artwork by artists of SW Oregon and Northern California. You will find a variety of mediums used, including oils, watercolors, and pastels.
  • Adelante! Gallery features fine artwork from local artist created with all mediums, including photography, sculptures, pottery, and jewelry.
  • Schneider Museum of Art is a contemporary art museum located at Southern Oregon University. It offers exceptional learning opportunities to both its students and the Ashland community.
  • American Trails Gallery features the artwork of America’s indigenous peoples.
  • Ashland Artworks features art quilts, jewelry, ceramics, furniture, sterling silver, and more. Their sculpture garden truly sets them apart!

Wineries, Breweries, & Dining

Ashland is famous for farm-to-table eats, vegetarian-friendly restaurants, and some of the most incredible wineries in Southern Oregon. Get a taste of the town at these spectacular wineries, breweries, and restaurants:

  • Grizzly Peak Winery is a delightful boutique winery located just 5 minutes from downtown.
  • Dana Campbell Winery offers a lovely tasting room with incredible views. It is only two miles away from downtown.
  • Greenleaf is an international eatery with delicious vegetarian, vegan, and gluten-free menus.
  • Amuse Restaurant is a refined French-style restaurant with dishes prepared with local, seasonal ingredients.
  • Coquina is an upscale restaurant which features Pacific Northwest cuisine.
  • Standing Stone Brewing Company offers fresh pizza, small bites, and great Southern Oregon craft beer.
  • Caldera Tap House is a local brewery with 20 beers on tap. Their food menu includes pub grub like nachos, burgers, and salads.


Downtown Ashland is home to dozens of boutique stores and independent shops. Whether you are searching for beautiful local artwork to brighten up your home or perhaps a new statement piece to add to your wardrobe, you will find it all here. Some of our favorite downtown shops and stores include:

  • Renaissance Rose (costume jewelry, masks, etc.)
  • Three Penny Mercantile (vintage and artist fashion)
  • Patina Soul (unique and contemporary clothing)
  • Bloomsbury Books (literature and books)
  • Lithia Artisans Market of Ashland (local artwork)

Book Your Stay at Country Willows B&B Inn

Country Willows B&B Inn enjoys a unique combination of proximity to downtown Ashland along with the peacefulness of the town’s countryside. Located just 10 minutes away from the downtown Plaza, our inn is the perfect place to stay and explore the best of what the area offers! All of our guests enjoy an array of special amenities, including onsite hiking trails, daily breakfast, and access to our beautiful pool and lounging area. 

Located in our renovated barn, the Creekside Suite is a lovely, secluded suite that features one bedroom with a California king-size bed, a spacious living room, dining area with kitchenette, and a sky-lit bath with a beautiful porcelain shower. This suite enjoys its own private entrance and outdoor porch with views of the surrounding creek, woods, and mountains! As an added feature, personal bikes may be kept close at hand just outside the door to the Creekside Suite in the barn’s interior. Start planning your next getaway and check our availability today! We can’t wait to host you at Country Willows B&B Inn!

Remember to download your free vacation guide to find more great things to do in downtown Ashland, OR!