This Laid-Back City Offers Big Travel Perks for Retirees

Portland, Oregon, is known for both its rugged Pacific Northwest beauty and distinctive urban vibe, earning it a place in many Americans’ retirement fantasies. At the same time, Oregon’s largest city is well-situated for retirees who want to hit the road, skies, or seas in search of other adventures. Here is what you need to know about Portland, especially if travel is high on your retirement agenda.

Travel Accessibility

Portland International Airport (PDX), northeast of downtown, is served by nearly 20 domestic and international carriers, with direct flights to more than 75 destinations.

PDX has undergone major renovations in recent years, with the new main terminal opening in August 2024. Some construction is expected to continue into early 2026. Portland calls the new facility the “local-est airport yet,” noting that it now has “100% local shops and restaurants.”

For rail buffs, historic Union Station near the city’s downtown offers daily service on several Amtrak routes. A block away, the Portland Transit Mall is a hub for Portland’s MAX Light Rail system as well as bus lines that cover a wide swath of the area.

Finally, Portland is located on the Columbia River, which connects to the Pacific Ocean about 100 miles to the west. While the Port of Portland is a major West Coast seaport, the city is less active in the passenger trade, with the exception of river cruises. American Cruise Lines, for example, offers a variety of multi-day tours on the Columbia and Snake Rivers with Portland as their starting point.

However, avid cruise travelers will find the Canadian city of Vancouver just across the border from Portland. Some 20 cruise lines sail from the Port of Vancouver, including Cunard, Holland America, Princess, and Royal Caribbean, with destinations that include Alaska, California, and Hawaii, as well as Canada’s Inside Passage.

Cost of Living and Affordability

Because of its desirability, Portland can be an expensive place to live. That’s driven largely by high home prices. Multnomah County, which encompasses Portland and the surrounding area, had median home values of $528,000, according to the most recent U.S. Census Bureau estimate. That was considerably higher than the national median of $303,400.

The Economic Policy Institute’s Family Budget Calculator (which takes into account housing, food, transportation, healthcare, taxes, and other necessities) estimates that a household with two adults and no children living in Multnomah County would spend $6,346 a month on average or $76,154 a year.

Zeroing in on taxes, the Tax Foundation ranks Oregon 30th among the 50 states for its overall tax burden (with 50th place being worst). That’s due in part to its high corporate and personal income taxes, which rank 49th and 40th, respectively.

The state fares better in terms of sales taxes, where it ranks 4th in the nation. In fact, Oregon has no state or local sales tax at all. “If there’s one thing that unites Oregonians, it’s opposition to sales taxes,” the Tax Foundation says.

Of particular interest to retirees, Oregon does not tax Social Security benefits. However, it does tax just about every other type of retirement income, including pension benefits and distributions from retirement accounts like 401(k) plans and IRAs.

Lifestyle Considerations for Retirees

Portland offers all the cultural attractions you might expect of a large city, including live music and theater, museums, gardens, and “the world’s largest independent bookstore,” as Powell’s Books bills itself.

Portland is also known for a lively restaurant scene. “Farm-fresh is the dish of the day, every day, washed down with an ever-expanding list of locally brewed craft beers, small-batch liquors and award-winning wines,” the website Visit the USA says.

The area also boasts plenty of parks and wildlife trails for hiking and cycling, and its location on the Columbia and Willamette rivers provides opportunities for kayaking and paddleboarding. Golf Digest reports that there are “49 courses within a 15-mile radius of Portland, 37 of which are public.”

To help retirees stay in shape for their travels, Portland also has an ample supply of health care facilities. For example, the Medicare.gov website lists 20 hospitals within a 25-mile radius, half of them with four- or five-star ratings.

Other Things To Consider

Idyllic in many respects, Portland is not without its problems. Like many cities with high housing costs, it has a serious homelessness problem. The City of Portland reports that, “Currently there are hundreds of unsanctioned camps spread out across virtually every neighborhood of our city,” adding that, “overall homelessness in Portland increased by 65% from 2015 to 2023.”

In a 2024 article titled “Is Portland a Good Place to Retire To?,” Portland Monthly magazine concluded that, “Portland may be less expensive than such West Coast rivals as San Francisco and Seattle, but many older residents—especially those on fixed incomes—find the city’s housing costs and taxes stultifying.”

On the plus side the author noted that, “Portland is hardly Palm Springs, but it offers plenty of options for the retiring set able to access them, who are lured by the natural beauty that has long attracted people (of all ages), plus new zoning laws that allow for two—and sometimes more—dwellings on lots where only single homes once stood.”

The Bottom Line

With easy access to domestic and international flights and the major cruise port of Vancouver not far away, Portland is well-positioned for retirees who want to explore the world. It also has an abundance of attractions in its own right. At the same time, it can be an expensive place to live, with high housing costs, high income taxes, and a potentially punishing estate tax.

As with scoping out other potential retirement destinations, it’s a good idea to visit the area during all four seasons and possibly rent there for at least a year before investing in a home. That way, you can decide for yourself whether Portland’s charms are worth the price tag that accompanies them.