Showcase Listing

Few towns in the Southeast offer more gracious charm than Aiken, South Carolina.  Take a relaxing stroll through Aiken's tree-lined ...

Showcase Listing

Bon Ayre is a 55+ active adult, manufactured home land lease community located in Smyrna, Delaware, a town which was recently ranked 31st...

Showcase Listing

Wendell Falls is a new, all-ages community located just minutes from downtown Raleigh, North Carolina, and features an eclectic, walkable...

Showcase Listing

Cresswind Charleston is Charleston-area's BEST active adult lifestyle community. Cresswind inspires active adults to live life to the ful...

Showcase Listing

Brookfield Residential at Two Rivers is a brand new community designed for those 55+, and offers an abundance of opportunities for a vibr...

Showcase Listing

Birchwood at Brambleton is an exciting new community for active adults 55+ located in the heart of Loudoun County, and is intentionally d...


10 Best Small and Mid-Sized Cities for Retirement

Category: Best Retirement Towns and States

May 27, 2021 — Not everyone dreams of retiring in an active community, a small town, or the suburbs. There is a sizable group of baby boomers who yearn for something bigger than that. For these folks, retiring in a small or medium sized city might be just the ticket. This lifestyle has the attraction of living in the center of things, walking to everything, choosing from a raft of interesting restaurants, or seeing a good play production or concert. To these folks that is a lot more appealing than endless rounds of golf, pickleball, or mowing the lawn. Here are picks for some great places to retire that offer an urban lifestyle.

For cities to be considered we had several wish list items, although not every city will have all of them. We tried to find cities that are walkable; where pedestrians enjoy wide sidewalks, safe crossing zones, and some separation from cars. Pedestrian-only zones are a big plus. Bike lanes and paths that keep you and your bicycle out of harm’s way from cars are nice to have. There has to be a number of good restaurants and cultural venues to choose from. The presence of a college or university definitely adds value. And finally, there should be some living options either in the downtown or in a quiet nearby neighborhood. Another bonus would be low cost of living (not all of our picks met that hurdle). We published a list of 9 Great Small Cities for Retirement a few years ago, and boy did that generate a lot of Comments and suggestions (199) – we think you will find them worth reading.

The definitions for small and a medium cities are imprecise. Wikipedia counts a small city as a community with at least 100,000 inhabitants, to distinguish it from a town. OECD defines small cities as having a population between 50,000 and 200,000. They count medium-size cities as places with populations between 200,000 and 500,000. We will include the population for each city listed, and we will use those figures as flexible guidelines.

10 Great Small and Medium Cities for Retirement:

St. Petersburg, FL. St. Pete offers a pleasant lifestyle near the water with many diversions. There are many interesting neighborhoods and attractions. It is home to three colleges. The area near the harbor offers an array of great restaurants for sidewalk dining as well as several museums. The revitalized St. Petersburg Pier is a huge tourist attraction.  The Tampa Bay Rays have their home in St. Pete. The population is 261,388.

Santa Barbara, CA. Located about 85 miles north of Los Angeles, this charming city of 91,364 on the Pacific has done a superb job of preserving its heritage and creating a livable, modern city. The graceful adobe architecture of the Spanish Mission style is everywhere. The Santa Ynez Mountains rise up 4000’ to the east and provide a stunning backdrop. Santa Barbara has an active cultural life with many museums and colleges (UC Santa Barbara and others). There are more than 15 notable parks, some of them quite large. You can choose to live in a house or apartment near downtown, or you can live in an apartment or free-standing house farther out in a development. Bring your checkbook, property is expensive here.

Charleston, SC. The 137,566 people who live in this old city enjoy one of the most beautiful cities in the U.S. Until the mid 1800’s it was one of the 10 largest cities in North America. The College of Charleston and The Citadel are just two of the institutions of higher education that are located here. Streets of pastel colored homes are lined with majestic and Spanish moss draped live oaks.

Boulder, CO. The city of 106,392 has won so many awards that the City’s official website has an entire page devoted to them – most focusing on best “Green”, “Bicycling”, “Running”, “Healthiest”, “Best Place to Live”. Both Modern Maturity and Money Magazine have listed Boulder as a top place for retirement. It has many parks and a plethora of cultural opportunities. Like Santa Barbara, its desirability also makes it very expensive.

Long Beach, CA. This is the largest city on our list (population 462,257). It gets very good scores for walking and biking, especially because of its miles of paths along the (long) beach. The weather is great and the outdoors is a treat almost every day of the year. There are colleges and cultural attractions as well.

Baton Rouge, LA This city of 220,000 is located on the Mississippi River near the “laces” of the Louisiana boot. A college town, it is home to Louisiana State University (LSU) and several other colleges – 20% of the population is made up of college students. Baton Rouge has the state capitol as well as a lively arts scene. The Shaw Center for the Arts opened in 2005, and it houses the Brunner Gallery, LSU Museum of Art, the Manship Theatre, a contemporary art gallery, and traveling exhibits. There are several performing arts venues including The Baton Rouge Little Theater, Baton Rouge River Center, and Manship Theatre.

St. Louis, MO The city of 319,294 has very good walkability.  Located on the Mississippi River, this historic town (gateway to the west) has many neighborhoods and a very rich trove of cultural and civic resources. The St. Louis Zoo and its arch are very famous. Washington University is one of America’s leading institutions. Urban revitalization continues in the new century. Gentrification has taken place in the Washington Avenue Historic District, Central West End and Forest Park Southeast neighborhoods. Crime is high, however, in many parts of the city.

Madison, WI This city has above average scores for walking and biking. The population is 229,493. A university town (University of Wisconsin), its downtown is located in the picturesque isthmus between 2 lakes, Lake Mendota and Lake Monona. State Street, a car-free zone, links the campus with the capital square. There are many other communities that have been incorporated into the city.

Asheville, NC. Walking around in downtown Asheville is a pleasure. It has a great collection of art deco architecture, antique stores, art galleries, and boutiques. Those who prefer the outdoor cafe or coffee house setting will enjoy its many cafes. The people are friendly. Asheville’s people range from artists and musicians to corporate executives, merchants and entrepreneurs. It is easy to park on street or on a parking deck, then stroll through the streets. The population is 92,800. No wonder this city is a perennial best place to retire.

Bozeman, MT This fast growing city had 49,000 residents in 2019, by now it is over 50,000. It offers an interesting, walkable downtown with many restaurants and shops. Many of the latter will be for outdoor gear, as recreation in the nearby mountains is world class. Yellowstone National Park is a fairly short drive away.

Comments? Do you have a dream of retiring in an urban environment? What towns did we leave out that we should have considered? Which places to retire should have been left off? Please share your thoughts in the Comments section below.

Posted by Admin on May 26th, 2021


  1. According to CoreLogic, home prices nationwide have shot up 11.3 percent over the past year. Huge increases for materials like lumber will make this worse. According to the NY Times, much of the growth and resultant price increases are happening in areas away from large cities. Small cities and exurban areas are seeing bigger increases than larger cities. See

    by John Brady — June 2, 2021

  2. St. Louis, are you joking? This is the murder capital of the USA. No one with options should ever think about moving here! St. Louis is a city in rapid decline.

    by James — June 2, 2021

  3. The idea of a small or medium city has a lot of appeal to me. I hate driving everywhere to conduct one’s daily life. One thing i wonder about is how the big cities will rebound, now that Covid is on the wane in the U.S. Can the exodus be reversed, or will it continue. The problem did not seem so bad in the smaller and medium cities.

    by Nick — June 3, 2021

  4. I find it interesting that many retired/retiring folks have a need to move to some distant state or land to find that perfect forever place to live. That favorite vacation place is not it. Keep it as a vacation place during retirement.

    In my many years of travel, I found that many towns/cities have sections/areas within (or close by) that have what one is looking for. Just because the current home/area is no longer desirable does not mean that the whole town/city/state is the same. So, instead of searching for retirement utopia several hundred/thousand miles away, look at a 30 mile radius from where one lives now. That way, one can still be close to family and friends and enjoy a new venue that meet one’s needs going forward. Just a thought.

    by Roland — June 4, 2021

  5. So, Roland, for us, we chased work across the country, even the UK, and back again. We loved living in New England (CT & RI) and went back a number of times, only to have the job disappear. As we hit retirement, we decided WE get to pick the place and STAY there this time. We made a methodical choice, landed in Maine and love it!

    Also, “retirement” is a new chapter in our lives. Perhaps we get to re-invent ourselves and do stuff we always thought we wanted to do but we worked at jobs we didn’t always like, to take care of our families and save up until we could try that something new. This is our time now! WE left the kids and grandkids behind to fend for themselves (okay, we were also the ones who left our parents behind and went out into the world) but, we’re loving the new home. I agree that its not always the best choice for everyone but thats our story.

    by HEF — June 4, 2021

  6. Hef, where in Maine did you end up? Thanks, Bill

    by Billy — June 4, 2021

  7. I just removed Asheville, NC from my list of possible retirement destinations.

    by Danno — June 4, 2021

  8. Roland, I totally agree with your thoughts on not moving far away in retirement. In some situations, it is a good idea to move closer to family if work has taken you far away from them. Or if you have a burning desire to move to a different location that you have dreamed of your entire life. But to move, just to move makes no sense. Seems the first thing out of people’s mouths when they find out you are about to retire is “where will you move to”! What? I have dabbled with the thoughts of moving elsewhere that is cheaper to live but starting over isn’t easy either. I think of the pro’s and con’s. I have more pro’s to stay put.

    by Louise — June 5, 2021

  9. It doesn’t necessarily require living in a small to medium-sized town to keep your driving to a minimum, or manageable amount. Although we live in the greater Miami metro, with a population of over 6 million, we chose to live in an area within that metro – Delray Beach – that has much of what we need within an easy driving distance. Several supermarkets and many restaurants, services, large public library and retail and big box stores are within a 7-10 minute drive. A 400-bed hospital and hundreds of related doctors’ (and dentists’) offices are also within that driving range. None of these destinations require getting onto an interstate. A major public university is a 20-minute drive away, and a smaller university with a strong emphasis on the performing arts is only a 10-12 minute drive. Two large airports (Fort Lauderdale and West Palm Beach) are a 25-35 minute drive away. Delray Beach also has a vibrant, very walkable downtown that still retains a good deal of its village charm. The downtown and beach are a 15-17 minute drive from where we live, again without getting on an interstate. Many large metro areas have towns or suburbs within them that have a smaller-town feel with lots of necessities and amenities just a short drive away.

    by Clyde — June 5, 2021

  10. Billy – As much as we wanted to be in a town with a beach, the prices (even in 2017) were prohibitive for our budget. We ended up in a small town, just west of Portland ME. Easy access to everything!! Sebago Lake is just west of us and Maine Medical has a large medical campus in Scarborough, to the east. North of us is progressively less expensive and Maine Medical is expanding slowly. Give it a look.

    Danno, we liked Asheville – in theory. Its artsy, fun and a little cooler in the summer BUT it is in the mountains and many of the streets are steep! Not so easy to walk around as you might think. We had a condo there for a while and you pretty much needed a car to drive to the mail box and back again. I could not walk it.

    by HEF — June 5, 2021

  11. Totally disagree with your list. Especially St. Louis, Asheville and Baton Rouge for crime and lack of policing and Charleston SC because they allowed it to grow way to fast, traffic, traffic, traffic especially during tourist season. Personally I’d throw Williamsburg Virginia on to that list. Even in tourist season, we, as locals are very much aware of alternate routes around town. They have everything and so much to do!
    I’ve found it to be a very safe area and even during COVID-19, only a handful of businesses went out, mostly breakfast restaurants of which there are already maybe too many! As a veteran, I love the accessibility of military bases for both health care and commissary usage.

    by Dave C — June 6, 2021

  12. I have looked at or visited many of the cities listed in this article. For the present, we are staying in Connecticut. It is not not the cheapest place to live but it offers a lot and its location is ideal with Boston to the north and NYC to the south with RI beaches nearby and Vermont is beautiful in the fall. If we did move to would either be RI or Maine.

    by Mark — June 6, 2021

  13. Thanks, HEF, I was in Maine two years ago, loved the lobsta and the region. New Hampshire is next. Billy

    by Billy — June 6, 2021

  14. Cost of living does not necessarily correspond to quality of life. I moved to RI and plan to stay put. Close to beaches, an hour away from Boston, and on the train to NYC. Medical care is often overlooked, but at our age, it make a big difference. Another factor for me is the political climate and diversity. The winters are fairly mild by the coast and it is pretty easy to get around with buses that run all over the state. For me, it is pretty close to a perfect spot.

    by Maimi — June 6, 2021

  15. I am trying to get information on Williamsburg, Virginia and not finding much. Mostly all that comes up is information on the active adult communities. We aren’t interested. Is Williamsburg incorporated as a city or is it part of New Port News. Any info to start a search would be great.

    by LynnB — June 6, 2021

  16. Louise – I heard the same question when I (and spouse) retired: “So, where are you guys moving to?” Yes, we moved, but only 25 minutes away. We happened to find a gem of a location with all the recreation and conveniences that we searched for years in other states (including reading many articles on the best places). Most of the conveniences (groceries, restaurants, banking, Post Office, department stores, doctor offices, etc.) are all within a 10-15 minute “walk”. Many other seniors walk here too. We drive only on bad weather days or have things delivered. We also have a 3+ mile nature path that have several access points for the residents.

    So, these places do exist and they could be just a short distance from where one is now. Instead of Googling far off places, drive around the area. Even places like St. Louis have hidden gems near by.

    Remember, if one decides to move, move for a good reason. Not because one wants to get away from people they are tired of being around. Who knows, it might not be them.

    by Roland — June 6, 2021

  17. I’m trying to get information on Maryland. It’s a very strange state, divided by inter coastal waterway. I’ve read some past info on your web site but I would like to hear more recent views. Thanks

    by Virginia — June 7, 2021

  18. LynneB. Yes Williamsburg is a city and one of the oldest in America…since it was laid out as a city in 1699! Try as a starting point. We’re not a part of Newport News. If you’re having any more questions about the area, maybe try contacting John Womeldorf though a realtor, holds the alter ego of Mr. Williamsburg for his vast and extensive knowledge of the area. Good luck in your search for information and maybe we can meet some day. I own a home in “one of those active adult communities” that seem to always come up in your searches (Colonial Heritage).

    by Dave C — June 7, 2021

  19. Hi LynnB and Virginia
    If you go to at the top of this page, you’ll see the menu on the right. There you’ll find State Guides listed where you can search for information on Virginia, Willamsburg, and Maryland. For example,

    Other sources are and Wikipedia. Topretirements also has Blog Articles and you can use the Search to find more info.

    Hope this helps!

    by Moderator Flo — June 7, 2021

  20. I’m kind of in awe of those of you who have chosen to age in the northeast. I just can’t take the cold anymore. I don’t love where I live and may relocate, but I’m in the south, which means I never have to worry about slipping on ice when I walk, driving on snow or ice or getting into a cold car for months on end. Kudos to you. I wish I could be more flexible about it, because the northeast fits me in so many other ways.

    My newest place to explore is Richmond, VA. Not as warm as where I am in SC, but has some qualities I am looking for. It’s not a city I hear a lot about. Anyone know it well?

    by Jes — June 7, 2021

  21. Jes, We did not look at Richmond but a friend of mine lived in VA and here are her thoughts:

    “I don’t know what the real estate market is right now, but it’s a pretty decent city. I know they did some crime prevention in conjunction with the urban renewal thing they had happening. Richmond would be a contender if I could go anywhere I wanted. I don’t remember anything about tax structure, senior advantages and that sort of thing. Richmond is far more progressive than most of the state outside of the beltway. The weather really isn’t bad at all. Winters are moderate, a few good snow storms and a few awesome tropical storms per season. Fair proximity to the ocean, easy access to anywhere on the eastern seaboard. Yeah… I wouldn’t mind it terribly at all.”

    by HEF — June 7, 2021

  22. HEF – thank you for that. So far I’ve only heard good things from the few people I know who have any information about Richmond.

    by Jes — June 8, 2021

  23. We moved from Rochester NY to the Richmond area, a bit south of the James River, about four years ago. Love spring, fall and winter. Summer is hot, but bearable. There is so much history in the area, as well as beautiful places to visit and hike. We’re two hours from the mountains and about two hours to the beach. Lots of well respected hospitals in the city as well as outlying communities. Plus about two hours to our family in DC (if traffic isn’t too bad), but an easy train ride up. We’re very happy here.

    by Patti — June 9, 2021

  24. Kudos to those who a braving it through the northern winters. I’ve found them harder and harder to tolerate as I get older and I’m several years from retirement. My RA just causes so much pain. I’ve been thinking of outside Nashville as a possible place to retire. Alternately, I’ve considered keeping our home and property in Northern Michigan as we love it and just renting somewhere warm for the 3 coldest months of the year. We could choose a different place each year if we wanted. Its just the 2 of us, no children and just a couple of sisters who are already retired. They would probably enjoy tagging along. I appreciate everyone’s comments and the articles.

    by Gaz S — June 9, 2021

  25. Gaz, I think you would find that most of New England has much more moderate weather than Michigan. Keeping your home and traveling for a few months a year sounds like a great solution.

    by Maimi — June 10, 2021

RSS feed for comments on this post. TrackBack URL

Leave a comment