9 Amazing Small Towns to Retire In

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Middletown, Conn.

Connecticut is well-known for its high-cost area, and Middletown makes no exception. However, the Hartford metro area which also includes Middletown, is the most affordable area, including Stamford and New Haven, as the Council for Community and Economic Research mentioned.

Plus, the local residents that are living there have no difficulty whatsoever making it work. The city’s average income for all types of households is $90,977 a year, and it gets even better for the elderly population with incomes for residents that are 60+.

As Middletown is also the home to Wesleyan University, you would benefit from ALL the perks that come with it: numerous restaurants, shops, and cultural attractions. You will also take advantage of the Wesleyan Institute for Lifelong Learning, where you can follow no-credit courses, lectures, and many other educational opportunities.

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53 thoughts on “9 Amazing Small Towns to Retire In”

    1. You’re right about that !! However if you happen to purchase or already own a property in a really desirable area, now a days, as a senior person, you can end up being harassed in rather sophisticated ways, just because someone one else wants your property.

      1. You’re so correct!! People are tired of being harassed by investors. They should buy and develop empty lots and foreclosed homes vs. bugging homeowners to no end.

  1. Regarding article by Dorothy ,”9 Amazing Small Towns to Retire In” Middletown, Connecticut is first. I grew up in Middletown and visit once in a while. Restaurants are a too many thing on Main Street,etc. The ability to purchase newspapers for local news is gone. Unless a college-related bookstore has changed its mind. It is no longer a Barnes/Noble corporate bookstore. Central News, a longtime outlet is long gone and is replaced by a sandwich shop. A lunch place called Ford News has no newspapers despite its name and serves meals like a diner till midafternoon . Also on Main Street north of that location is another diner. Both have been main stays on Main Street long before these new food palaces arrived on the scene and seem to give Middletown its new reputation. As for Wesleyan Univ., one must live downtown to only walk to campus for amenities. Middletown Area Transit buses operate Mon-Sat 6am-6pm only. I would like my former city to be like other New England towns with a operating main street. Grocery stores have left downtown also. Drug stores also are gone from downtown

      1. Bruce, I believe she is talking about the changes, including the local newspapers, which we all like. I feel her pain….my hometown turned into a poverty-stricken sad town. The Main Street I loved….is taken over by homeless, and often drug dens. Bruce, I think we should focus on how to bring back the feeling of safety and love we felt in our hometowns, so that our grandchildren, etc., will know how sustaining a “hometown” can be.

        1. I concur with Melanie. Newspaper access is important. A local grocery store is also important. As baby boomers, it is important to still have memories of our bygone era too. I despise college towns because of the rude students who don’t have respect for retired people and they always want change to accommodate their own selfish needs.

        2. I just reviewed this posting. I live in PA, grew up here outside of Philadelphia suburbs.
          Lived in Maine(to much snow), Texas (Tornados scary), then Florida (to many Hurricanes),
          came back to PA feeling I can deal with occasional snow. We have plenty of medical facilities, Grocery stores, Pharmacy and local businesses. I own my home convenience I love this area 35 yrs. Wonderful with Historical Sites,museums and local activities.

    1. Thak you for your input! This does not sound like a retirement friendly town and not one I will be considering! Most on this list seem to be college towns and especially after all the violent protests lately i wouldn’t want to be anywhere near them! i will come up with my own list!

    2. I’m with you. Retired and looking. I want to sit on Main Street sip on some coffee and read a local newspaper. If I feel the need for more drama I’ll turn on CNN.

  2. You are out of your minds! Recommending ice boxes like Montana, Minnesota, New England states, etc. to us old geezers with aches and pains and no desire to tread on snow and ice is a total non-starter.

  3. I have a strong feeling that these candidates for “best” are bought and paid for. Older folk with their chronic issues typically hate the cold.

  4. Pretty ridiculous if anyone thinks reading an article like this is going have any value to anyone other than Dorothy. Seriously. There are so many other factors to consider, such as normal weather patterns (do you love summer and despise cold winters? Is near constant rain ok? What weather disasters are known to occur, such as tornados or hurricanes, or floods, or earthquakes, etc., the general character and social tones of long-time locals (some populations really are not very welcoming to outsiders, and some are), any major food differences, major political issues, specific churches that may be nearby or not…. and on it goes.
    So the housing costs, restaurants, hiking trails, etc. are all fine to look at, but gotta think about the realities of probable daily life.
    Make a list of any and ALL things you’d like to have in your perfect town, and hold nothing back. Nothing. Get as crazy and unreasonable as you want. Then prioritize each desire till you have three or more levels of importance ranging from “I’d be totally miserable without” to “it’d be really nice if”. By searching only for the top “must haves”, you may identify a list of viable places worth looking at closer. In the process, it’s likely priorities will shift, as well, as you discover the realities of finding or not finding that town where it’s warm all year, they practically give houses away, there’s zero crime, they all LOVE and fawn over the elderly, and it’s all clothes optional all the time. (Ok, that’s MY list, not yours, but report back here if you find such a town, plz!)

  5. I would say Preskitt, AZ is a good place to retire, however; Housing market is high like anywhere else, people mainly from California are retiring here, traffic is actually bad here (no one follows the speed limit here, people do run stop lights and stop signs), women drivers and old people drivers are the worst here (almost every incident that I’ve been in (crossing the intersection and no one stopping, either a woman or an old person was driving, and even almost ran over one day by who? A middle aged woman.), the town is slowly becoming progressive.

  6. No, I am retired, and before they fund everyone they need to pay us retirees that worked their butts off to work to retirement and paid into what was known as S/S. Another way for people to sit on their butts and not have to do NOTHING to pay for their way!!!

    1. Your complaint is people getting S/S. If you are getting it. You only get what you put in. No one is getting what you paid in. So how is this making people not pay their way. You get yours. If someone becomes disabled they draw what they paid in. .

    2. Since you seem to have way too much time in your hands, try this
      Figure out how much you actually paid into social security when you were working,
      Then figure out how much you have collected AND WILL CONTINUE TO COLLECT UNTIL YOU PASS

      And then you’ll realize what a ridiculous post you just made

  7. not one place on your list interests me! everything is up north! hate the cold and Snow, even a little is not for my liking! HI. is to small and no where to go once you learn the island then your done!

  8. Spent a week in Charlottesville, Virginia checking out the city, visiting historic sites, museums and parks. Some lovely things about it but our family found people there really snotty and unfriendly, unwelcoming. The food scene was disappointing, didn’t find any of it memorable or worth returning to. Southern hospitality in Charlottesville? Nope. We’ll tgake Richmond anytime, a totally friendly vibe there and a lack of pretension too.

  9. There seems to be a liberal tone to this selection of the nine best towns to retire. Each one has tax issues for seniors. Very poor selection. There are much better places to live then these.

  10. You’re so correct!! People are tired of being harassed by investors. They should buy and develop empty lots and foreclosed homes vs. bugging homeowners to no end.

  11. I hate these list, they are only made to make you change to page after page filled with ads. Want the best 9!or whatever, only needs 1 page, then you can go into detail. I will unsubscribe from any and all adbate pages and suggest EVERYONE else do the same …

  12. Myra Speller

    We all will have a problem in the future. America has changed, no one is looking out for the middle class. It seems that everything is placed on our backs. Every year I am paying more and more taxes and getting less and less support from the government. The roads are in a shamble home taxes keep rising.

    I don’t know what’s the answer to solving these issues. But I am not in the government and not expected to be one to solve these issues.

  13. I’m with you. Retired and looking. I want to sit on Main Street and sip coffee and read the local newspaper. If I feel the need for more drama I’ll turn on CNN.

  14. Cheryl is spot on. I was a democrat for 40 years after seeing what the left has done to dismantle the country and what hey do to those that speak out against them and letting in 18 million free loaders and trouble makers ( they are not all bad ) but were going to be sorry you just wait and see , in law enforcement for a lot of years now have family members in it all say the same thing if you don’t currently have protection you better get it cops are fed up and leaving in droves the left has created a pro crime venue that we have not seen the in the last 70 years, it’s coming . our only chance, GO BRANDON god help TRUMP. Vote republican and pray.

  15. get ready for about 3 months of decent weather in all of these burgs followed by a mud room full of galoshes and mittens. See you in the spring in about nine months

  16. Everyone of these areas are controlled by progressive liberals! Who needs or wants the craziness and the anti America hassles dealing with the crazy blue people!!!

  17. Most of these are on the east coast. Why nothing but Minnesota in the center of the country? I’m sure Texas has some good cities for retirement.

  18. I didn’t see any “small” towns in your article. I identify a small town as being less than 10,000. Where as they say everybody knows everybody.

  19. We the people need to get a law passed that states, once the government raises, puts aside or already has money for a specific project or program, THEY CAN NOT UNDER ANY CIRCUMSTANCES, take, borrow, or use the money’s for any reason other then what the money is specified for. That includes any foreign aid & ILLEGAL immigrants

  20. I personally despise the ads you place in specific locations and no longer will I read anything you publish

  21. All of these states are way too expensive to retire to. They are not tax friendly states. They are in no way senior friendly. I do t know who wrote the article but they missed the mark.

  22. Paul kilgallon

    All sounds like the aftermath of the Biden camp! Nice work to the stupid people that voted for him.

  23. We have to vote and vote for the personwho protect social security and Medicare and not give it away to people who are not citizens

  24. LOL now that is funny. They say Hilo Hawaii is expensive, than they list Bozeman Montana.
    Hawaii is dirt cheap compared to Bozeman Montana. Want to go broke, move to Bozeman or Flathead valley. Montana is extremely expensive.

  25. who comes up with this list. Some of the most expensive places to live and that is where you want people to retire to…………..really.

  26. Why are you using an aerial photo of Sarasota, Florida as your headline photo when the city isn’t listed? Makes one wonder about the accuracy of your article.

  27. This entire “retire in usa” is so obviously pro Trump and his party! Why are you couching your hidden agenda in articles to help seniors and sneak these thoughts into their heads? You should be ashamed. Please give us information, but don’t do it in such an underhanded, sly, snakelike manner. Leave the politics out and give clear, transparent information. By the way, any true patriotic American will never vote for a habitual liar, cheating on his wife, draft dodging, tax evading, racist, women no choice, no church going person like Trump. Just look at the facts. Oh and by the way, remember the Billy Bush interview? Keep your mother’s, daughter’s and wife’s private out of arm’s length of Trump. This man failed 1st grade where I was taught not to lie, cheat, steal or call people names like fat and ugly! Open your eyes and call it what it is.

  28. This entire “retire in usa” is so obviously pro Trump and his party! Why are you couching your hidden agenda in articles to help seniors and sneak these thoughts into their heads? You should be ashamed. Please give us information, but don’t do it in such an underhanded, sly, snakelike manner. Leave the politics out and give clear, transparent information. By the way, any true patriotic American will never vote for a habitual liar, cheating on his wife, draft dodging, tax evading, racist, women no choice, no church going person like Trump. Just look at the facts. Oh and by the way, remember the Billy Bush interview? Keep your mother’s, daughter’s and wife’s private out of arm’s length of Trump. This man failed 1st grade where I was taught not to lie, cheat, steal or call people names like fat and ugly! Open your eyes and call it what it is.

  29. Most are ultra liberal towns; no to that. Liberals are arrogant, think they are better than everyone else, most are Godless. That would be hell living around people like that. Sure there will be exceptions to that, but that is just what it is, a smaller number of exceptions.

  30. I wouldn’t touch any of these “so-called” retirement places! Yuck and yuck. Who came up with this list and how did they come up with the “criteria” for this list?? Wasted my time skimming through it.

  31. Are you fucking retarded? This is the worst compilation ever. Every town mentioned is a POS liberal town with freezing weather.

  32. Currently a lifelong resident of Erie Pa. Great place to live and I do it for less than $1500. a month. Winters are much milder and summer, spring, and fall is much warmer. It has a beautiful lake and forests. Surprised that it isn’t listed for one of the most reasonable?

  33. Every single one of these places is way too expensive to live for retirees, except possibly West Virginia, but I may be wrong! Do some research and it’ll tell you to stay away from those states as retirees!! The Northeast is not where retirees want to be! Connecticut? Are you serious?? How old is the journalist writing this piece…25??

  34. I didn’t find the nine cities or what ever but I found like of anti-trump scare stuff the left will do anyhing to stops trump and gop and that means lie all day long

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