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.

Brookings

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 and mild winters, Brookings is a beautiful community bordered by the Coastal Range Mountains to the east and the Chetco River along the south end. The town has a population of just under 7,000 and offers plenty of outdoor activities and cultural experiences to explore. It is home to numerous restaurants, markets, and breweries, including the Superbly Distilling Company, Chetco Brewing Company, Misty Mountain Brewing, and Tap House. Brookings hosts various seasonal events, such as 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 during summer. The town also boasts excellent outdoor facilities like Azalea Park, which features disc golf courses, ball fields, and a playground; Chetco Point Park, with a beachside fenced dog park; and the Port of Brookings Harbor, including a marina, beach access, and numerous dining and shopping options.

Ashland

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

A slightly larger community with over 21,000 residents, Ashland ranks among 'The 100 Best Small Arts Towns in America.' Retirees can spend their days exploring and creating in this Oregon town's rich cultural scene while nestled between the Siskiyou and Cascade mountains. The town also hosts 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 featuring art galleries to browse. Ashland is also home to Mt. Ashland Ski Mountain, a great destination for both winter and summer activities, from skiing and snowboarding to mountain biking and hiking. This town offers enough culture and outdoor adventure for a fast-paced lifestyle or a more relaxed one focused on 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.

Silverton

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 ideal spot for those who love beautiful foliage and pristine gardens, and who want to spend much of the year outdoors enjoying their own flower beds. With a population of just over 10,000, Silverton is a tiny community nestled in nature and outdoor spaces. One of its highlights is the Oregon Garden, a thriving 80-acre city-managed garden, along with miles of trails featuring ten waterfalls in Silver Falls State Park. There are plenty of opportunities for walking, hiking, biking, and horseback riding to explore Oregon's backyard. Silverton's charming downtown is about half an hour from Salem, offering easy access to larger communities and services without losing its small-town charm. When residents want to stay indoors, they can explore the Frank Lloyd Wright Gordon House, Lunaria Gallery, and the twelve Cascade Foothills Wineries. The town has around a dozen restaurants and bars, plus easy access to farms and orchards for fresh, farm-to-table eats. Silverton is an excellent community for a beautiful retirement surrounded by flowers, good food, and great wine.

Sisters

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

A small community with fewer than 3,000 residents, Sisters has a distinctly Western American vibe compared to other small towns in Oregon. Each year, the town hosts a three-day "take-over-the-town folk festival" during which a rodeo joins the local festivities, blending into the town's wilderness and boutique-filled downtown. Although it’s small, Sisters experiences fluctuating tourism, ensuring a constant flow of interesting people coming and going to meet and learn from. Besides its many annual folk events, like the September Sisters Folk Festival and the June Sisters Rodeo, the town features a lively downtown with clothing boutiques such as Bedouin and The Jewel, along with restaurants and cafes like Sisters Coffee.

Astoria

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

A museum and history junkie's dream, Astoria is home to numerous museums such as the Columbia River Maritime Museum, Flavel House Museum, and the Oregon Film Museum. This historic coastal city has a population of around 10,000 people. Surrounded by three rivers and forests, and known as a lively fishing community, Astoria boasts a rich heritage. The town is also famous for its brewery scene, featuring spots like the Bridgewater Bistro, Shallon Winery, and the Wet Dog Cafe and Brewery. Known as the "Little Town that Could," Astoria takes pride in its culture and community, driven by passion and perseverance. It’s an excellent place for anyone looking to pursue artistic, professional, or athletic passions or 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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