Living in Ashland Oregon: A Comprehensive Guide
If you're considering living in Ashland, Oregon, whether for work, retirement, or simply a change of scenery, you're in for a treat. This comprehensive guide will cover everything you need to know about this charming town—from its vibrant neighborhoods to local culture, and even the pros and cons of living here. As the home of the renowned Oregon Shakespeare Festival and beautiful Lithia Park, Ashland offers a unique blend of arts, nature, and community spirit.
Table of Contents
- Why Choose Ashland OR?
- Best Neighborhoods in Ashland OR
- The Cultural Scene in Ashland OR
- Outdoor Activities in Ashland OR
- Pros and Cons of Living in Ashland OR
- Frequently Asked Questions About Ashland OR
- Conclusion: Is Ashland OR Right for You?
Why Choose Ashland OR?
Ashland is a small city nestled in the southern part of Oregon, approximately 16 miles from the California border. With a population of around 20,000, it boasts a welcoming community feel while offering a range of amenities typically found in larger cities. The town is known for its stunning landscapes, cultural events, and outdoor activities, making it an attractive destination for people from all walks of life. Ashland's picturesque surroundings include rolling hills, lush parks, and winding trails that invite residents and visitors to explore its natural beauty. The vibrant downtown area features charming shops, local eateries, and art galleries, contributing to the town's unique character and charm.
What truly sets Ashland apart is its cultural richness. Home to the renowned Oregon Shakespeare Festival, the city draws theater enthusiasts from near and far, eager to experience world-class performances. In addition to theatrical productions, Ashland hosts various art festivals, music events, and community gatherings throughout the year, fostering a strong sense of connection among its residents. The emphasis on the arts is evident in the numerous galleries displaying works by local artists and the vibrant street art that adorns the town.
Outdoor enthusiasts will find that Ashland offers an abundance of recreational activities. Hiking, biking, and skiing are just a few of the outdoor pursuits that residents can enjoy year-round, thanks to the nearby mountains and parks. Lithia Park, a centerpiece of the community, provides a serene escape with its walking paths, botanical gardens, and tranquil creek—perfect for picnicking or simply unwinding amidst nature. Whether you’re seeking adventure or a peaceful retreat, Ashland caters to all preferences, making it an ideal place to live, work, and play.
Best Neighborhoods in Ashland OR
One of the most appealing aspects of living in Ashland is the diversity of its neighborhoods. Each area has its own unique character, catering to various lifestyles and budgets.
Granite Street Area
Granite Street is one of the best locations in Ashland. It is known for its historic homes and proximity to the Plaza and Lithia Park. Here, you can find beautiful old homes, some listed for over $4 million, while others offer more affordable options in the $500,000 range.
This neighborhood is not only desirable for its stunning homes but also for its walkability. Residents can easily access local restaurants, shops, and cultural attractions like the Oregon Shakespeare Festival.
Ashland Hills Neighborhood
Just a short drive from the downtown area, Ashland Hills offers stunning views and luxury homes. The homes here are often multi-level, built into the hillside, providing spectacular vistas of the surrounding landscape. Prices can range from $600,000 to multi-million dollar estates.
While the views are breathtaking, keep in mind that this area may not be ideal for families with young children learning to ride bikes due to its steep terrain.
North Mountain Area
The North Mountain area features newer construction homes and is perfect for those looking for modern amenities. This neighborhood is situated near North Mountain Park, which offers baseball fields and walking paths, making it a great choice for families.
The Cultural Scene in Ashland OR
Ashland is perhaps best known for its vibrant cultural scene. The Oregon Shakespeare Festival, America's first Elizabethan theater, attracts visitors from around the globe.
In addition to the festival, the town is home to numerous art galleries, theaters, and music events throughout the year. The community places a strong emphasis on the arts, making it an enriching environment for both residents and visitors alike.
Local Cuisine
If you're a foodie, Ashland will not disappoint. The town features a diverse culinary scene with dozens of restaurants offering everything from gourmet to casual dining. Notable spots include:
- Osteria La Briccola: An Italian restaurant known for its homemade pasta.
- Alchemy Restaurant and Bar: A highly-acclaimed restaurant that has been featured in national publications.
- Skout Taphouse & Provisions: A great place for local beer and bites.
Don't forget to check out the Ashland Food Co-op, which prioritizes locally sourced and organic products, making it a favorite among health-conscious residents.
Outdoor Activities in Ashland OR
Living in Ashland offers endless opportunities for outdoor activities. The town is surrounded by beautiful landscapes, including:
- Hiking: Access to the Pacific Crest Trail and numerous other trails for all skill levels.
- Biking: Mountain biking trails are abundant, especially around Mount Ashland.
- Skiing and Snowboarding: Mount Ashland is just a short drive away, offering winter sports activities.
- Water Activities: Immigrant Lake provides options for kayaking, fishing, and paddleboarding.
Pros and Cons of Living in Ashland OR
While Ashland offers many benefits, it's important to consider both the pros and cons before making your move.
Pros
- Cultural Richness: The arts and cultural events are a major draw for many residents.
- Community Spirit: A welcoming community that fosters a sense of belonging.
- Natural Beauty: Stunning landscapes and outdoor recreational opportunities.
- Quality Schools: The Ashland School District is highly rated, making it a great choice for families.
Cons
- Cost of Living: Ashland is one of the more expensive areas in Southern Oregon.
- Isolated Location: The town is somewhat isolated from larger cities and amenities.
- Parking Issues: Finding parking in downtown can be challenging, especially during peak tourist seasons.
- City Council Regulations: Some residents feel that local government policies can be overly aggressive.
Frequently Asked Questions About Ashland OR
Is Ashland, Oregon a good place to retire?
Yes, Ashland is often considered a great place to retire due to its mild climate, rich cultural scene, and beautiful surroundings.
What activities are available in Ashland?
Residents can enjoy hiking, biking, skiing, and attending various cultural events throughout the year.
How is the healthcare in Ashland?
Ashland has a community hospital and is within driving distance of larger medical facilities in Medford.
What is the average home price in Ashland?
The median home price is around $600,000, but there are options available at various price points.
Are there good schools in Ashland?
Yes, Ashland has a highly regarded school district with several elementary schools, a middle school, and a high school.
Conclusion: Is Ashland OR Right for You?
Living in Ashland, Oregon, offers a unique blend of culture, nature, and community. With its vibrant neighborhoods, rich cultural scene, and abundant outdoor activities, it's no wonder that many people are drawn to this beautiful town. If you're considering a move, take the time to explore all that Ashland has to offer!
For more information, feel free to reach out to me, Brian Simmons, and I would be happy to assist you in your journey to discover Ashland.

Buying Southern Oregon
At Buying Southern Oregon, we are a dynamic team dedicated to helping you achieve your real estate goals. Combining Brian Simmons’ deep market expertise and Josh Berman’s strong negotiation skills, we provide personalized service and local knowledge to ensure a seamless and rewarding experience. Whether you’re buying, selling, or relocating, we’re here to guide you every step of the way and make your Southern Oregon real estate journey a success.