604 Fair Oaks Ct, Ashland, OR 97520

Downtown Ashland, Oregon – What To See, Eat, and Do

Downtown Ashland, Oregon is a happening place with a small-town vibe. It’s easy to get around, there are amazing restaurants, and plenty to see and do. For those unfamiliar with everything Ashland as to offer we’ve made this handy guide to help you explore all of the best things to see, eat, and do in downtown Ashland, Oregon.

Downtown Ashland Oregon Looking Down E. Main St.

Where is Downtown Ashland, Oregon?

Unofficially, the downtown area in Ashland stretches along a ½ mile strip of Siskiyou Boulevard from the Ashland Public Library up to Calle Guanajuato and through Lithia Park. Along East Main St. and Lithia Way you will find the majority of businesses located in the downtown area from restaurants and cafes to boutique shops and offices.

Google Map of Downtown Ashland Oregon

How To Get Around Downtown Ashland, Oregon

Ashland is easy to get around and walking is usually your best option for getting around downtown. Ashland is also a bike-friendly city with a bike-share program, a central bike path, and plenty of places to lock up throughout town. And, the city of Ashland, Oregon is a Certified Bicycle Friendly Community so you can feel safe while you’re pedaling around town. You can even stop by Ashland Electric Bike Rentals to rent an Ebike for the day!

Best Places to Check Out in Downtown Ashland, Oregon

Make your way past the Ashland Library and down toward the plaza taking by taking East Main.

Walk past the Ashland Oregon Library

Feeling Thirsty? Stop By NW Raw Organic Juice Bar

Start your day off right with a delicious juice smoothie or healthy snack at NW Raw Organic Juice Bar.

    • Address: 370 E Main St, Ashland, OR 97520
    • Hours: 7 am-7 pm every day

Check Out Varsity Theatre

The Varsity Theatre is a community landmark and one of the coolest movie theatres you may ever see. 

    • Address: 166 E Main St, Ashland, OR 97520

A true Ashland landmark in Ashland Oregon. Stop by and see the Varsity Theatre.

Peruse Earthly Goods

Earthly Goods is a cool boutique shop with an excellent selection of quality fashion and footwear for women.

      • Address: 142 E Main St, Ashland, OR 97520

Go See The Oregon Shakespeare Festival

Take a left on S. Pioneer St. and prepare to enter Ashland’s most acclaimed attraction, the Oregon Shakespeare Festival. The Oregon Shakespeare Festival (OSF), is a nationally respected, multistage theater complex that’s one of the largest and oldest theater companies in the country. Give yourself a tour and then make your way down into Lithia Park.

      • Address: 15 S Pioneer St, Ashland, OR 97520

Head Down To Lithia Park’s Lower Duck Pond

Right behind the Allen Elizabethan Theatre, there lies a peaceful place called the Lower Duck Pond inside Lithia Park. This is a  great place to sit and people, read a book, or watch the ducks go about their day. It is also the entrance to Lithia Park, so take some time to walk through the park and take in your beautiful surroundings.

      • Address: 17-341 S Pioneer St, Ashland, OR 97520

Lower Duck Pond in Lithia Park

Take a Sip Of The Famous Lithia Water

Once you’ve taken a stroll through the park head across the street from the Lower Duck Pond to find the Lithia Fountains on the Plaza. Yes, you can and should drink from them! Ashland, Oregon is famous for the lithium-rich water that gurgles from a fountain in the center of the Plaza. Some say it has magical healing powers, but regardless of its health benefits it is an experience you won’t soon forget. Check out this video to see for yourself 😉 

      • Address: Lithia Fountains, N Main St, Ashland, OR 97520

Grab a Bite To Eat at Oberon’s Restaurant & Bar AKA “Ashland’s most Ashlandiest Spot” 

“For those who seek the unique, value the arts, crave home-style meals, prefer craft beer or have an affinity for creative cocktails, Oberon’s Restaurant and Bar is your destination. Oberon’s Restaurant and Bar is a colorful hub of music, food, drink, and laughter for the culturally adventurous and playful at heart, perfectly blending modern art and renaissance culture.”

      • Address: 45 N Main St, Ashland, OR 97520

Check out Ashland's most Ashlandiest Spot

Stroll Down Calle Guanajuato

After you have enjoyed a tasty meal at Oberon’s or one of the other amazing restaurants on the Plaza walk around the back of the stretch of buildings where Oberon’s is located toward Ashland Creek. On the weekend, you will find a local artisans market here and people enjoying a meal sitting at one of the creekside restaurants.

      • Address: Calle Guanajuato Park, Ashland, OR 97520

Take a stroll down Calle Guanajuato in downtown Ashland

Enjoy A Tasty Treat At Rocky Mountain Chocolate Factory

Do you have a Sweet Tooth? Stop by the Rocky Mountain Chocolate Factory to fulfill your afternoon chocolate craving. This Chocolate factory is known for its friendly service and a large variety of tasty treats all made in house!

      • Address: 33 E Main St, Ashland, OR 97520

Go Thrift Shopping At Three Penny Mercantile

This vintage clothing store is a must for any thrifty shoppers! The Three Penny Mercantile’s mission is “to stay true to the idea of self progression, ever-changing, non-stagnant, un-uniform, healthy, comical, free-spirited  approach to life and individualistic expression whether in personal presentation or display.”

      • Address: 101 E Main St, Ashland, OR 97520
      • Hours: 10 am-8 pm Every day

Take In Some Locally Made Art At The Ashland Art Center

The Ashland Art Center is a one-of-a-kind gallery showcasing some of the best artists from around the Rogue Valley and beyond. Head inside and wander through the galleries. There is even a wine bar to add to the experience and daily art classes you can sign up for.

Ashland Art Center

Whether you’re visiting us or new to town we hope you enjoy exploring Ashland! Have you been to Ashland before? If so, what other hot spots would you add to this Downtown Ashland, Oregon Guide?

At KDA Homes, our mission is to be pioneers in smarter home design leading the way for sustainability in residential development and green building. If you’re interested in being a part of a sustainable community in Ashland, Oregon please contact us today to learn more about KDA Homes currently on the market.

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