Portland, Maine

For seniors who don’t want to give up city life, Portland offers all the amenities of an urban center without the chaos; it’s clean, safe, and friendly with a strong community that has a small-town feel. 

Driving around is typically stress-free: Traffic congestion doesn’t plague Portland as it does most cities. That’s if you even want to drive at all—the waterfront city is incredibly walkable, from the downtown center to Old Port. The Greater Portland Metro bus system also makes it easy to get around.

With ocean views and, in classic Maine style, stunning lighthouses, Portland is rich in opportunities for avid sea lovers. Fishing, boating, kayaking—it’s all possible here. On land, there are plenty of green spaces for walking and biking, from the Eastern Promenade to Deering Oaks Park. For a change in scenery, the six islands of Casco Bay are just a ferry’s ride away for a day trip exploring more of Maine’s beauty. 

The city itself has plenty of cultural events to keep retirees busy: There’s a Biennial Arts & Culture Summit, an art walk every Friday, and a community of more than 500 career artists always showcasing or performing their work. That’s not to mention Portland’s buzzy food scene, from Eventide Oyster Co. to the Duckfat restaurants.  

And as Maine’s largest city, with more than 68,000 people, Portland has a host of volunteering opportunities retirees can choose from. It’s overall very welcoming to seniors, as the first Maine community to join AARP’s Network of Age-Friendly Communities. The Portland Office of Elder Affairs/Age-Friendly Portland was recently awarded nearly $8,000 to help make local businesses and nonprofits more accessible to seniors and those with mobility challenges. 

Plus, there are a variety of housing options, from historic homes to senior living communities to waterfront condos, so retirees are bound to find something that fits their lifestyle.