Mount Hood and Hood River Town.

6 Towns Perfect for Retirement in Oregon

Oregon sits near the northwest corner of the United States, just north of California and south of Washington State. It is known for its diverse ecological diversity, including rainforests, mountains, plains, and countless national wonders such as the Oregon Caves National Monuments, the Cascade Range, and the Columbia River. Due to its heavy tree-covered mountains, the state's leading economy centers on lumber and wood products. A hub for both nature and culture, Oregon is a safe and beautiful state to relocate to for retirement. Most of its towns are on the smaller side, but the state is home to over four million people to meet and explore the state.


Panoramic view of Brookings, Oregon jetty and harbor entrance, captured by drone.
The panoramic view of Brookings, Oregon jetty, and harbor entrance was captured by drone.

Located on the Wild Rivers coast, with a warm ocean climate, mild winters, the Coastal Range Mountains to the east, and the Chetco River running along the south end, Brookings is a beautiful community with no shortage of outdoor activities and culture to explore. The town's population sits at just under 7,000. Brookings is full of restaurants, markets, and breweries, including the Superbly Distilling Company, Chetco Brewing Company, Misty Mountain Brewing, and Tap House, among others. Brooking's has no shortage of seasonal activities to explore, including Whale watching from Harris Beach State Park, the Winter Art & Chocolate Festival each February, the Pirates of the Pacific Festival each August, and the American Music Festival every Sunday throughout the summer. The town is also home to excellent outdoor facilities such as Azalea Park, which is home to disc golf courses, ball fields, and a playground; the Chetco Point Park, including a beachside fenced dog park; and the Port of Brookings Harbor, including a marina, beach access, and several dining and shopping options to browse through.


Aerial view of Ashland, Oregon.
Aerial view of Ashland, Oregon.

A slightly larger community with over 21,000 residents, Ashland is in the top 10 of "The 100 Best Small Arts Towns in America." Retirees can spend their days exploring and creating this Oregon town's rich cultural scene while nestled in between the Siskiyou and Cascade mountains. The town is also home to unique events, such as the Ashland Mystery Festival, which takes place each October. The local theater is the oldest Elizabethan theater in the United States, offering performances 365 days a year and hosting art galleries to peruse. Ashland is also home to Mt. Ashland Skii Mountain, which is an excellent destination for winter and summer sports alike, from skiing and snowboarding to mountain biking and hiking. This town provides enough culture and outdoor excitement for a fast-paced lifestyle or a more leisurely one centered more around good food, music, and company.

Hood River

Mount Hood and Hood River city
Mount Hood and Hood River Town.

Only an hour's drive away from Portland and three hours from Seattle's major international airport, Hood River is a tiny rural community with strong connections to the rest of the world. With a population under 9,000, this small community is an all-season cultural hub. Life in Hood River is incomplete without frequent visits to its cultural and commercial heart, such as the Fruit Company, which is both a local heritage museum and a functioning orchard gift shop. Known for its agritourism as the U.S.'s largest exporter of pears, there is also fresh food, fresh culture, and living agricultural history to embed oneself in. It is also home to the Western Antique Aeroplane & Automobile Museum, among several indoor and outdoor galleries and exhibitions. For those yearning for a consistent farm-to-table economy and lifestyle, whether on a small patch of land or in town after weekly grocery stops at the Eliot Woods Farn, McCurdy Farm, and Kiyokawa Family Orchards, Hood River may just be one of the best places in the continental U.S. to realize this lifestyle.


Cityscape along Silver Creek in Silverton, Oregon, USA.
Cityscape along Silver Creek in Silverton, Oregon, USA.

Known as Oregon's Garden City, Silverton is the place to be for those who love beautiful foliage, and pristine gardens, and who want to spend the bulk of the year outdoors enjoying their own flower beds. Home to slightly over 10,000 inhabitants, Silverton is a tiny community embedded in nature and the outdoors. Most impressive, the Oregon Garden is home to a growing 80-acre city-run garden, miles of trails with ten waterfalls in the Silver Falls State Park, and ample walking, hiking, biking, and horseback space to explore Oregon's backyard. Silverton's cozy downtown is located roughly half an hour from Salem, giving you easy access to more prominent communities and services without sacrificing small-town living. When it's time to turn indoors, residents can spend their days exploring the Frank Lloyd Wright Gordon House, Lunaria Gallery, and the twelve Cascade Foothills Wineries. There are roughly a dozen spots to eat and drink in town and easy access to farms and orchards to eat directly from the land. Silverton is an excellent community for a beautiful retirement embedded in flowers, good food, and good wine.


A view of the main street in downtown Sisters, Oregon.
A view of the main street in downtown Sisters, Oregon. Editorial credit: Bob Pool /

A tiny community with under 3,000 residents, Sisters has a more Western American vibe than other small Oregon communities. Every year, the rodeo comes to town over a three-day "take-over-the-town folk festival," mixing into the town's wilderness and boutiques-filled downtown. Although tiny, Sisters sees a lot of fluctuating tourism, meaning that there will never be a shortage of interesting people coming and going to meet and learn from. Aside from its numerous annual folk events, such as the September Sisters Folk Festival and the June Sisters Rodeo, the town boasts its vibrant downtown full of clothing boutiques such as Bedouin and The Jewel, as well as restaurants and cafes such as Sisters Coffee.


The Liberty Theatre in downtown Astoria, Oregon, a city landmark.
The Liberty Theatre in downtown Astoria, Oregon. Editorial credit: BZ Travel /

A museum and history junky's dream, Astoria is home to countless museums, such as the Columbia River Maritime Museum, Flavel House Museum, and the Oregon Film Museum. Astoria is a historic coastal city with a population of roughly 10,000 people. Astoria is surrounded by three rivers, and forests, and is a bustling fishing community known for its rich heritage. The town is also known for its brewery scene and is home to several spots, such as the Bridgewater Bistro, Shallon Winery, and the Wet Dog Cafe and Brewery. Known as the "Little Town that Could," Astoria is proud of its culture and community, which are dedicated to passion and perseverance. Astoria would make an excellent home for anyone looking to continue their artistic, professional, or athletic passions or for anyone looking to discover their next great adventure.

A Rewarding Retirement Awaits in Oregon

Oregon is an excellent choice for many retirees looking to relocate and settle. With no sales tax and a relatively low-income tax rate, not only is Oregon an intelligent decision for investing your money, but it is also a state that will love you back. From its gorgeous and rolling landscapes, offering everything from coastal to high mountain living, rich agricultural and cultural scenes, and warm and moderate climates, Oregon has all the qualities that will provide a stable, rewarding, and enriching retirement.

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