The Best Cities to Live in Oregon

Combining spectacular scenery and a high quality of life, it’s no surprise that Oregon consistently makes it to lists of the most sought-after places in the US.  Residents enjoy the pristine natural beauty of its lush forests, fertile valleys, sandy beaches, and snow-covered mountain peaks. The state offers a high quality of life that makes it a great place to settle for retirees, young families, and everyone in between.

In 2018, a survey by moving company United Van Lines ranked Oregon as the second most popular state for people to migrate to. In Oxfam America’s 2021 Best States to Work Index, the Beaver State took the top spot, jumping several notches higher from its fifth place ranking in 2020.  The global anti-poverty organization also ranked it as the Number 1 state for working women.  

If you’re thinking of moving to Oregon, one of the first things you need to do is find the right community for you. Start with this comprehensive guide, which discusses some of the best cities to live in Oregon, as well as important things you need to know about making this beautiful area your home. 

Best Cities to Live in Oregon

Oregon is a state of contrasts. Bounded to the west by the Pacific Ocean, it boasts approximately 362 miles of rugged coastline that encompasses Highway 101 – considered one of the most scenic drives in the United States. Every inch of the coastline is open to the public, providing epic views of the ocean and breathtaking cliffs dotted with lighthouses, as well as long stretches of golden sand that seem to go on forever.

Meanwhile, Central Oregon is home to a high desert as well as the Cascade Mountain Range with its snow-covered peaks. It is here where you’ll experience truly out-of-this-world sites, such as Oregon’s Moon Country, where the lava fields of Newberry National Volcanic National Monument served as a training site for Apollo astronauts during the 1960s.

In the fertile valleys of the state are world-famous wine regions and AVAs hosting over 900 wineries. Along with the coastal areas, these wine regions comprise some of the best cities to live in Oregon. 

Whether you choose to live by the beach, mountains, or fertile wine valleys, Oregon has something to match your preferences. In finding the right city, town, or neighborhood for you, consider each region has to offer. 

The Best Cities in Southern Oregon

If you love being surrounded by the raw beauty of Oregon’s forests, mountains, and lakes, Southern Oregon is the perfect choice for you. The region is also home to some of the top wineries in the state, providing a refreshingly rustic landscape and laidback way of life. On top of all these, the area is a major cultural destination, with a rich history that has been enhanced by highly popular festivals and events. 

Looking for the best city to live in Oregon? You will love what these southern communities have to offer. 


Tucked between the majestic Siskiyou and Cascade mountain ranges, Ashland is one of the best cities to live in Oregon. With its population of roughly 21,000, Ashland boasts a charming small-town vibe except when it hosts the world-famous Oregon Shakespeare Festival, when approximately 400,000 visitors come to the city and turn it into a bustling mecca for theater lovers.

This gorgeous southwestern Oregon city is home to the 175-acre campus of the Southern Oregon University, giving it a vibrant college town vibe. Residents enjoy warm sunny weather for 200 days each year, providing plenty of time to soak up the sun at Crater Lake National Park or rafting on the Rogue River. In the winter, Mount Ashland provide 200 acres of skiable terrain, and its snow-capped peaks are perfect for sightseeing tours.


The close proximity of the city of Talent to Ashland makes it an excellent base for those who want to make the most of the economic opportunities in the area but love to come home to an idyllic country lifestyle. 

Situated in the picturesque Rogue River Valley, Talent is home to one of the state’s oldest wine regions. This city has a population of around 6,500 residents but its 24-year-old community theater Camelot Theatre Company draws visitors from all over Southern Oregon and beyond. Some of the best hiking trails in Oregon can be found in the nearby Siskiyou Mountains, which boasts exceptional biodiversity. 


Starting out as a Western gold-rush town in the 1850s, Jacksonville is known as one of Oregon’s oldest communities. This historic town features homes made in 19th-century Classical Revival, Queen Anne, and Craftsman architectural styles, some of which have been transformed into modern condos.

Southern Oregon’s secret gem is also known for the Jacksonville Wine Trail, which hosts the annual Oregon Wine Experience, an event the puts the spotlight on the Rogue Valley’s finest wines from over 100 wineries. Situated in the breathtaking foothills of Oregon’s Siskyou Mountains, Jacksonville continues to attract homebuyers for its thriving epicurean and cultural scene. 


If you’re dreaming of moving to a place where you can be close to wineries and breweries, as well as myriad outdoor adventures, Medford will check all your boxes. 

Not to be missed is Crater Lake, the deepest lake in the United States, known for its pristine blue waters and towering cliffs. Enjoy swimming, kayaking, canoeing, or jet boating in the “Wild and Scenic” Rogue River. Hike to the top of Table Rocks where you can get spectacular bird’s eye views of the Rogue Valley. 

Considered to be the fourth largest metro area in Oregon, the nonfarm payrolls of Medford outperformed the state average in 2020. In the past 10 years, the labor market in Medford has increased by 11.5%. The biggest employers are two major medical centers, while assisted living and senior services are also important economic drivers in the community. 


Located in scenic Rogue Valley, Phoenix offers an endearing small town charm while providing quick and easy access to the economic opportunities in nearby Ashland and Medford. The city’s downtown area offers an unhurried retail and dining experience, with local shops and restaurants featuring unique and distinctive fare. 

A must visit is Phoenix Industrial Studios, an innovative shopping center housing a variety of small businesses. The city also boasts excellent wine tasting rooms for some of the best wineries in Rogue Valley, such as Ryan Rose Wines, Goldback Wines, and Sound & Vision Wine Company. 

And of course, there’s the great Oregon outdoors. With over 35 acres of land dedicated to parks, trails, and greenways, Phoenix provides a quick getaway into the best that nature has to offer.

Central Point

If your idea of the perfect lifestyle includes great wine, cheese, and chocolate, you can’t find a better place to settle than Central Point. This charming countryside community is located right smack in the heart of Rogue Valley, surrounded by some of Oregon’s best wineries, as well as the country’s top cheese and chocolate makers.

Central Point is home to Rogue Creamery whose blue cheese was named the best in the world in 2019. Each year, the creamery hosts the Oregon Cheese Festival, a signature event showcasing the city’s long tradition of excellent cheese making.

Just a short distance from Rogue Creamery is Lillie Belle Farms, famous for its handcrafted artisan chocolates. Named one of America’s Top 10 Chocolatiers, Lillie Belle Farms offers a wide range of chocolate flavors, including quite a few that you can’t find anywhere else.

All these fine cheeses and chocolates make the perfect companions to some of Oregon’s finest wines produced in Central Point’s five AVAs. The area is major stop in the famous Bear Creek Wine Trail, one of the best reasons to visit the state. 

Other Amazing Cities in Oregon

Outside of Southern Oregon are a host of distinctive cities that make the state a vibrant mx of the old and the new. You don’t need to travel far to have a fun and diverse adventure. Simply take a short drive and explore these other distinctive Oregon cities.


Oregon’s largest and most populous city, Portland has a booming economy, thanks to the presence of big-name companies such as Boeing, Columbia Sportswear, Intel, and Nike. The average household income in Portland is higher by almost $4000/year than the national average, which makes this city a great location for job seekers. 

In 2021, Portland was named by U. S. News & World Report as one of the ten best metro areas to live, as well as one of the safest places to live in the country. 

Those pursuing higher education will be spoiled for choice since Portland is home to renowned institutions, such as the Portland State University, University of Portland, and the Oregon Health & Science University. 

Coos Bay

There are plenty of reasons why Coos Bay is an excellent place for anyone to call home. It is the largest city on the Oregon Coast but it manages to retain its suburban vibe. Moreover, its close proximity to Coos Bay makes it an excellent location for people who want to settle down near the water. Families will enjoy spending weekends exploring the numerous beaches or engaging in adrenaline-pumping water sports. The city also has a lower cost of living index compared to the state and the entire country – one of the reasons Coos Bay is one of the best cities to live in Oregon. 


One of the three biggest cities in Oregon, Eugene has an enviable location close to the Pacific Ocean and to verdant mountains. Head west and you’ll reach the Oregon coast, with its free public beaches, soaring cliffs, and picturesque lighthouses. Head east and you’ll reach lush rainforests and the breathtaking mountains of the Oregon Cascades. Get an adrenaline rush by rafting and kayaking on the Willamette River and the McKenzie River.  

Dubbed as the Emerald City, Eugene is known for its vibrant arts scene and for being home to the 295-acre University of Oregon, one of its largest employers. Other major employers include the PeaceHealth Medical Group and the Eugene School District 4J. 


Nature lovers will love moving to Bend, which is a shortened version of “Farewell Bend.” More than 100 years ago, pioneers named this area Farewell Bend because it was where they bid their goodbyes and forded the Deschutes River before heading further west. 

Bend, which is nestled between Oregon’s high desert and the Cascade Range, is known for its pristine beauty and adrenaline-pumping outdoor adventures. Residents can go whitewater rafting or kayaking in the Deschutes River, or go hiking in the Central Oregon Hiking Trail. In the winter, you can go skiing or snowboarding on Mount Bachelor. This city has become very popular in recent times. In fact, according to the U.S. Census Bureau, Bend reached a growth milestone when the population crossed the 100,000 mark in 2019. 

Things to Know About Living in Oregon

Moving to the Beaver State is one of the best decisions you can make in life. To have a successful transition, it’s best to familiarize yourself with the area and make the necessary preparations.

Here are some of the things you should know about this beautiful state. 

Real estate market update

Analysts say it is a good time to buy a home in Oregon now if you  want to avoid further price increases. According to Neighborhood Scout, the average home price in the state rose 6.55% from the first to second quarters of 2021. Annually, the increase has been a staggering 28.87%. 

According to, the average home price in Ashland, Oregon has increased to $600,000 in September, 2021 from $525,000 in September, 2020, an improvement of around 8.75%. In the last two years, home prices in the city have gone up around 26%.

Key history highlights

When prospectors struck gold in Sutter’s Mill, California in 1848, ambitious miners flocked to southwest Oregon in the hopes of making it big. But many pioneers chose to settle in the fertile territory of Oregon instead of staying put in California. 

The Oregon gold rush boosted economic development in the area, as the locals supplied neighboring California miners with products such as wheat and timber. By the late 1860s, the gold rush euphoria had died down, leaving behind ghost towns in its wake. 

When the gold miners moved on, farmers and merchants revived the economy by starting a robust winemaking industry. To date, winemaking is one of the most profitable industries in Oregon, and wine tourism is one the major reasons numerous families and retirees are drawn to the state.


The imposing Cascade Mountain Range, which separates the western and eastern parts of the state, brings wide climatic variations in the area. In the winter, heavy snowfalls are experienced in the Cascade Range. Winter can also bring polar cold waves that cause temperatures in inland areas to drop to as low as -20 °C. Meanwhile, summer temperatures can go as high as 44 °C (111 °F). 

Southern Oregon has a mild climate that makes it ideal for agriculture, particularly for growing grapes and other fruits. The Rogue Valley is still known as pear country, a nickname it has earned for the many pear and other fruit orchards that proliferated here.

Tax advantages

Moving to Oregon can be a good idea for retirees since the state exempts Social Security retirement benefits from taxation. Oregon is also one of only five states in the country that has no sales tax on purchased good. 

Explore the Best Cities to Live in Oregon 

Find the best community to live in the Beaver State with the help of the local experts in Ashland Homes Real Estate. 

Equipped with more than 40 years of experience, Ashland Homes Real Estate is the firm that you can trust to help make your dream home a reality. As you’ll see when you sort through our homes for sale, you’ll find houses that come in all shapes, sizes and styles. We specialize in selling everything from suburban homes to rural properties. We also have homes available to suit nearly any budget.

Real Estate for Sale

If you would prefer to purchase real estate for sale and build on it as opposed to buying a home that already exists, Ashland Homes Real Estate, Inc. can assist you with this, too! We have real estate for sale in Ashland, OR and many of the surrounding areas. What’s more, we can help you find exactly what you’re looking for, regardless of whether you want to buy it to build your dream home or purchase it as an investment.

Contact us at 800.334.7499 or email info(at)ashland-homes(dotted)com with any questions or to learn more about a house or property that piques your interest.