8 Best Oregon Towns For Retirees
Golf, bike, or watch the rodeo while enjoying the added benefit of no sales tax across central and eastern Oregon. Retirement here can play out in a drier and warmer climate than much of the state sees. Days might be spent near the Ochoco National Forest and Crooked River or out around the high desert of Prineville. Try your luck at a Pendleton casino or find community at a senior center in The Dalles. The antique Old West feeling of many of these places will draw retirees wanting a return to simpler times in their golden years.
Sisters

This series starts near the heart of Central Oregon in Sisters. Despite its smaller size, Sisters has a particular advantage for outdoor recreation in this former pioneering lumber town. Stare out at the clear night sky and identify constellations by Whychus Creek at Sisters' Creekside Campground. The 20-plus miles of Peterson Ridge Mountain Bike Trails take adventurers out into views of the craggy peaks of the Cascade Range, with specified horse trails for equestrians looking to exercise their companions, too.
To relax those muscles and fill that appetite after a long bike ride, have an old-fashioned burger or ice cream at the vintage-themed Sno Cap Drive In, a favorite local business established in 1954. And, retirees can become an active part of the community by volunteering at Sisters Community Garden, benefiting themselves and others through growing yummy produce and strengthening connections in the town of Sisters.
Prineville

About a 50-minute drive east of Sisters, Prineville is a high desert town roughly 45 minutes from the conveniences of Bend. Time outside can be spent playing 18 holes on Prineville's Crooked River at Meadow Lakes Golf Course, with no specific membership required, and having a hearty American meal at their onsite Ron's Comfort Food Cafe.
Across the river, Ochoco State Scenic Viewpoint has plenty more green space for walking and picnicking, with 360-degree views of the often blue-tinted Ochoco Mountains. And further up the river, the Ochoco Preserve, as part of the Deschutes Land Trust, has wetlands where McKay Creek and Ochoco Creek connect to the Crooked River, providing 185 acres to see native Chinook salmon or steelhead fish on a guided tour. Willows grow thick along the banks of the Crooked River through this area. For a change of scenery, retirees can watch professional rodeo at the Crooked River Roundup Rodeo, continuing the classic Old West traditions of this area. These attractions make Prineville a place where retirement can be enjoyed exploring the Oregon wetlands and making the best of a western small town setting.
Baker City

Venture out on the US Route 26 East and Oregon Route 7 for about four hours from Prineville, where you'll find Baker City, another former Old West habitat. Golf is available here, too, with the moderately challenging 18-hole Quail Ridge Golf Course with Creston's for grub, and views of the surrounding Elkhorn Mountains and Wallowa Mountains. Concerning local small businesses, Sweet Wife Baking puts the baking into Baker City, winning over residents with homemade macarons, breads, and more.
Art is an important facet of Baker City, besides its sweet treats and nature spaces. Artistic hubs like Crossroads Carnegie Art Center are scattered across the town, supporting and developing some of the region's most talented creatives through sales galleries, plein air events, and classes for both adults and children, made for retirees looking to get their hands on creating their own art or purchasing a community member's piece of art. And during the summer, older folks might appreciate going for a tour or simply walking past the architecturally Italian-inspired Adler House Museum, a symbol of Baker City's past, one final piece that will make retirement here well-rounded with chances for retirees to get in touch with their creative side or enjoy golfing on the green.
La Grande

45 minutes north of Baker City, La Grande is typically known as a college town, home to Eastern Oregon University, full of antiquated pieces of architecture. Only a short walk from the university, La Grande's downtown strip is marked by favorite eateries, such as the colorfully pink La Fiesta Mexican restaurant, offering weekly specials on margaritas and tacos. Roughly midway between the college and the downtown area is Art Center East, keeping the community involved in its creative scene with art classes and annual events like the wintertime Handmade Holidays Makers Market, where retired individuals can show off their creations.
Toward the western outskirts of town, La Grande Country Club welcomes new members to its nine-hole course and clubhouse, who may be retirees seeking a place of sport and leisure in their newfound retirement. Another outdoor space elderly folks who have dogs might want to check out is Riverside Dog Park to the north for play and socialization, fulfilling canine and human interaction needs. La Grande's community suggests a retirement in a historic town with a blend of creativity, good food, and opportunities to get outside with family and friends.
Pendleton

The theme of the Old West continues up in Pendleton, about 50 minutes northeast of La Grande, another smaller area in Oregon with a rich history in pioneering, which means it's naturally got a fantastic rodeo at the Pendleton Round-up Grandstand every year by the Umatilla River, flowing through Pendleton. This is right by the Pendleton Round-up & Happy Canyon Hall of Fame, honoring the cattle and men who participate in the rodeo, as well as Native history with artifacts like beadwork.
Retirees who want to live in a place where traces of the 19th century remain might appreciate Pendleton for that reason, not to mention the Wildhorse Resort & Casino in the neighboring Umatilla Reservation. Comedy duos and golf are two of the entertainment factors here, and retirees can join Club Wild for special hotel rates for a staycation playing slots or bingo. A retirement in Pendleton can be spent reliving the pioneering days of the US with plenty of amusement and areas like the Pendleton River Parkway for a reconnection with nature along the Umatilla River.
Hermiston

A little over half an hour from Pendleton is Hermiston, a small Eastern Oregon city with plenty of green spaces to bring together loved ones and get some light exercise, like at Riverfront Park on the Umatilla River or at Hat Rock State Park with its distinct formation in the dry sagebrush hills of Oregon. Fish for rainbow trout, jet ski on Lake Wallula, or hike here.
Get the support you need at the Harkenrider Senior Activity Center, with programs like Meals on Wheels running to serve the older percentage of the community. And the recently opened Hermiston Family Aquatic Center teaches water aerobics and lap swimming for getting exercise in water. There is also Hale's Tavern, a go-to spot after a swim or for taking the grandkids out for big portions of American food with stereotypical western furnishings. Hermiston has a wide variety of outdoor activities and is well-connected to other parts of Eastern Oregon, including a community that seems to support its older population.
Umatilla

Just a short 10-minute drive up from Hermiston lies Umatilla on the banks of the Columbia River. Nugent Park and Umatilla Landing Park, the latter set near where the Columbia and Umatilla rivers meet, offer quiet reflection on a bench or on a walk by the water, or a spot for hosting events like a retirement party. These two parks are by where the older parts of town once were, and where the Union Pacific railroad ran through, now just sites for imagining those times. There is also the Umatilla Marina Park for boating on the Columbia River, or fishing or picnicking.
Regarding local places to eat, The Bridge Bistro & Brews is a popular watering hole, treating retirees to scrumptious burgers and salads, with in-house reservations possible. They often have events on, like live music in the evening, making Umatilla a good spot for smaller community gatherings in a scenic riverfront location, plus the added bonus of a low cost of living here.
The Dalles

An hour and a half west of Umatilla is The Dalles, about 133 miles north of our first location, Sisters. This semi-rural town has its well-known Bargeway Pub & Catering restaurant on the water of the Columbia River, where The Dalles sits, almost as part of the 8-mile Riverfront Trail. This area has been shaped by melting ice sheets, resulting in interesting rock formations that can be viewed for miles.
In the rather historic part of The Dalles, the Mid Columbia Senior Center gives older people assistance, connection, and a range of activities, including bingo twice a week and low-cost day trips to regional sights like the Goldendale Reindeer Farm. But in the surrounding area, there are art centers, homesteads, and wineries like Sunshine Mill. Book a small group tasting for 10-20 people, or an on-site tasting for parties up to eight. There are also two clubs, Heritage Club and Founder's Club, that retirees can join for additional perks. The Dalles seems to be a geologically and historically fascinating place, as well as boasting great food and riverfront walks.
Plan Your Retirement in Oregon
Eastern and central Oregon's excellent proximity to the great outdoors, a host of community programs meant to keep seniors healthy and connected, and home-cooked food at cozy restaurants turns this state into a strong candidate for a fulfilling retirement. Plus, no sales tax here! Take a look at this list to find what might be where you spend your seniority, in the more remote landscape of the Wallowa Mountains or by Hat Rock State Park, and find yourself in the rustic pioneering terrain of this Pacific Northwest state someday. Many of these areas have a relatively low price tag, too, compared to other parts of Oregon.