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Where Are the Prettiest Places to Retire?

Category: Best Retirement Towns and States

October 28, 2014 — (Note: See our 2016 version with even more beautiful places to retire) Your editor was at a family wedding a few weeks ago when one of our smart young nephews surprised us with a question. Daeson, who was curious about, queried: “What is the prettiest town you know about?” The unexpected question stunned me, maybe because there are so many choices. I didn’t have a good answer.

Eventually I managed to stutter out Naples, Florida (to which the good wife said, Naples?), and Lucca, Italy. In the days afterwards I came up with many more, better possibilities. The exercise made me realize that it might be a really good idea to go further afield and ask you, our esteemed Topretirements members, what you think are the prettiest towns. In the interest of keeping on topic, let’s concentrate on towns that would be great for retirement, leaving out obvious tourist towns where retirement wouldn’t be such a great idea. Feel free to suggest any town in the world, not just the USA. It might be a good idea for you to provide a few words about what you think it is pretty. And no harm meant to Naples (FL), it has a very beautiful downtown and neighborhoods near the beach. But it also has a lot of sprawl and endless developments too.

A Pretty Towns for Retirement Sampler
To get started, we will provide a list of some of the communities from our database of 1,000 towns that we know enjoy a reputation for being particularly attractive. Note that many people think the prettiest towns are in the mountains, while others prefer small towns. Some dream about living on a lake or a coast. And yet others think there is nothing prettier than a college town. For more ideas please see the list of articles we link to under “Further Reading” at the end.
mount dora yacht

Mount Dora, Florida. We once wrote a Blog post about the prettiest town in Florida, which featured Mount Dora. What we like about this Central Florida town is that there is a beautiful park which the downtown is laid out around. The central streets are pretty. And connected to the downtown area is a pretty lake and the Elizabeth Evans park.

Santa Barbara, California. One of the cool things about Santa Barbara is the long main drag, which goes by historic old buildings, parks, and then ends up at the ocean. The homes are beautiful, and so are the surrounding hills. Of course this whole area between Los Angeles and San Francisco is spectacular, which includes the nearby wine country town of Solvang. Mendocino, which is above San Francisco, is another really pretty California town.

St. Francisville, Louisiana. We asked a friend who lives in the deep South for recommendations on great places to retire in that area. He recommended St. Francisville, and the pictures make it obvious why he came up with this town on the Mississippi.

Charleston, SC. Everyone wants to visit the old city of Charleston, SC, nicknamed the Holy City. It has beautiful architecture, pastel homes, a waterfront, and extensive history.

Charleston, SC

Galena, IL. Many beautiful homes and buildings in the French Colonial and Victorian styles of architecture were created during its early economic prominence due to steamboats and lead mining. Today it is a popular tourist destination, hosting over one million visitors each year. An amazing 85% of the structures in Galena are listed on the National Register of Historic Places.

Stonington, CT. New England is full of beautiful towns, but Stonington sticks out as one of the best. This old fishing village is almost totally surrounded by water. There is a very cute main street, a historic lighthouse, good restaurants, and the boating is terrific.

Camden, Maine. Known as the “Jewel of the Maine Coast”, Camden is popular for its beaches, harbor, and cultural opportunities. Although winters are chilly, it is an ideal 2-places for retirement location.

Hanover, New Hampshire. Downtown Hanover has an enormous square, on which and around is the campus of Dartmouth College. You will find cute shops, restaurants, and beautiful homes. The town is located on the pastoral Connecticut River.

New Braunfels

New Braunfels, Texas. It’s famous with tourists and retirees for its rich German heritage, festivals, and medical access. People love the people, weather, excellent health care, beautiful hill country and safe living environment, and many good restaurants. New Braunfels is over-flowing with old world heritage and small town Texas charm. The Gruene Historical District is a big tourist attraction.

Northfield, Minnesota. This pretty little town has several claims to fame. It is the home of 2 colleges (St. Olaf and Carleton College), and the site of a Jesse James attempted bank robbery in 1876. The latter is celebrated every year in a festival – funny how history turns out!

Bottom Line
Pretty to one person might be plain to another. That’s why we would like to get your opinions of the towns you think not only are exceptionally beautiful, but are also great places to retire. Please share your thoughts in the Comments section below – and we look forward to reading them.

For further reading
Prettiest Town in Florida
Classic Old Florida Towns
College Towns Make for a Great Retirement
5 Big Reasons Why Small Towns Are Great Places to Retire
10 Great Places in the Mountains for Retirement
The Best Places to Retire on a Lake

Posted by Admin on October 28th, 2014


  1. Essex, CT, on the east side of the state, is a lovely little town!

    by ella — October 29, 2014

  2. Beaufort, SC – beautiful low-country small town, waterfront downtown with restaurants, galleries, and gorgeous antebellum homes – smaller version of Charleston, with many sea islands and Hunting Island State Park nearby! Perfect for those of us who cannot exist without sand in our toes!

    by SandyZ — October 29, 2014

  3. Juneau, Alaska is one of the most beautiful cities in the world. It has it all – ocean, mountains, varied terrain and a surprisingly mild temperature. It is great for people who love adventure, the outdoors, and nature. From the top of Mount Roberts looking down on the city and all of the surrounding islands, while the sun sets, you may just fall in love.

    by Pat B. — October 29, 2014

  4. I lived 33 years in San Francisco, which I would argue is the prettiest city in the US. If you have plenty of money, it’s a great place to retire. I also think Sedona, AZ and Prescott, AZ are both very pretty towns. Sedona is probably pretty expensive, but I think Prescott is a bit more moderate. I also think Bartlesville OK is pretty, and it is very inexpensive.

    by Ginger — October 29, 2014

  5. Chattanooga, TN. Scenic beauty all around, a reinvented downtown that is a magnet for tourists (the Aquarium, the Riverfront, the Arts District, the Hunter Museum of Art). Lively cultural scene, a Minor League baseball team, friendly people, affordable cost of living, manageable traffic. We moved here from the NY Metropolitan area and are completely happy with our choice.

    by Mimi — October 29, 2014

  6. Decorah Iowa is a beautiful retirement location with its scenic limestone bluffs and the family – friendly Upper Iowa river for canoeing and kayaking. Decorah is also home to Luther College and Vesterheim, the Norwegian – American museum. A vibrant downtown with lots of shopping and restaurants, and a nice bike trail bring many visitors to Decorah. World class health care (Mayo Clinic) , good golf and tennis facilities, and a low cost of living make retirement in Decorah highly desirable.

    by Rich — October 29, 2014

  7. Mountain Brook, Alabama

    by Marianne — October 29, 2014

  8. The only one of these towns I’ve seen is Northfield MN which I’ve seen 3 times and believe me, it is just a delicious town. Perfect size, scale, charm, resources, amenities, the works. OK, I’ve never been there in January, but what with global warming trends… the winters everywhere will be getting milder over time. Northfield is a gem.

    by Leslie — October 29, 2014

  9. Mimi,
    I was thinking of one of the small towns near Chattanooga, but then i read the area is highly prone to tornadoes and that scared me away. I live about two hours north of NYC; and, as you know, we don’t have that problem here. Do you have any input on this issue for me? Thanks!

    by ella — October 29, 2014

  10. Interesting…the number of northern towns. I know Stonington CT is beautiful, but $$$

    by Ed — October 29, 2014

  11. Mimi-I second Chattanooga! We moved here from Naples, Florida and I think Chattanooga is much prettier than Naples. Where did you move to in Chattanooga? We are downtown in a condo and love the beauty, plus a walkable downtown. Grocery stores, a pharmacy, banks, hair salons, yoga salons, pet grooming, physical therapists, restaurants and shopping are all within walking distance. Love it here!

    by LisaJ — October 30, 2014

  12. Try Duluth MN, terrible winters, but with Lake Superior in your backyard some of the best natural scenery ever. Also check out Redding Ca, can’t beat Mt. Shasta for a back ground.

    by marvL — October 30, 2014

  13. Mimi/LisaJ & others-I am interested in knowing more about Chattanooga/Nashville and other TN areas. Heard there are pretty places over there, and want to know first hand about weather (hot sticky Summer & tornadoes?), pollution (air, water?) and local crime rates (conducive to raise a family?). We are currently selling our home in southern CA, and learning to find a good ranking High School for our Sophomore daughter to go to-is downtown, or suburban, Chattanooga a better choice? Thank you for sharing more details with us!

    by buddy — October 30, 2014

  14. I agree with Mountain Brook, Alabama. I loved the Birmingham area when I lived there and I was right on the border of Mountain Brook. But the summers are HUMID. And although B’ham is very dirverse and has friendly folks that welcome folks from anywhere…I did not find the same friendliness and yankee acceptence in other parts of AL. But if you can tolerate HUMID, I think AL has a few great areas for retirees.

    by EMA — October 30, 2014

  15. I have to thank the publisher for never mentioning Wyoming in these articles, because we are full! There is no more room for people here (I hear that Oregon is nice).

    by Gary — October 31, 2014

  16. Gary,
    May we still visit in the summer?

    by Sandie — October 31, 2014

  17. Buddy-summers are warm (usually July and August are the hottest) however, nothing compared to Florida. We have been in Chattanooga for 4.5 years and have not had a Tornado here. From my understanding it doesn’t happen often and their are many older buildings downtown (meaning they are still here) and add to the charm. Water and air are good (probably because Chatt is very forward thinking with a big emphasis on healthy environments). Chattanooga is a great place to raise kids with many private schools. If you are thinking public schools I would seriously consider Signal Mountain High School which is 5-10 minute drive from downtown.

    by LisaJ — October 31, 2014

  18. Sandie, Without tourist money, our liberal lodging taxes would be moot! Our usual well-groomed highways would turn (back) to potholes (although it is said that Wyomingites prefer potholed roads). So please come and touch our mountains and pet our wolves, grizzly bears and jackalopes, but don’t forget your Visa card! And remember, when your Visa runs out, so must you 😉

    by Gary — November 1, 2014

  19. LisaJ-thanks for the info! With divine’s blessing, we will put your area in our list to visit and explore first with the hope to stay in the future.

    by buddy — November 2, 2014

  20. We had the joy to visit Wy in early September a few years ago. Breathtaking scenery and delightful people. When we learned about the very long, and very cold winters, we took our warm memories back to Virginia. (Especially after they explained what those gates near the interstate exits are for!!!)

    by Sandie — November 2, 2014

  21. Sandie, I’m glad you have some warm memories of Wyoming! My bride of 40 years and I have lived here since our wedding, but not without a occasional dream of moving to warmer surroundings. After many travels we’ve decided to continue our stand here but we got our passports and have become Snow Birds; no particular place (just getting out before those gates close ahead of us)! The five or six months of relatively mild weather compared to something like Phoenix in July are (still) simply wonderful for both of us! Also: grandkids 😉

    by Gary — November 3, 2014

  22. We just last week returned from a 3 week cross country trip to find a place to retire. Hands down Colorado was the most beautiful. We looked at many houses that met our needs and the prices compared with south Fl were astonishing. In a good way! Countryside is beautiful and depending on how rural you want to be you can have peace! We also visited Ocala, Fl on the way home where things are much more reasonably priced and you can have some acres and peace. Now we just have to make up our minds this week…decisions, decisions!

    by Lorrie — November 3, 2014

  23. Has anyone considered northeast coastal North Carolina? These are the protected inner banks where the outer banks are not too far away. Far enough away yet close to everything. Abundant wildlife, sunsets on the Albemarle Sound, reasonably priced housing and affordable amenities.

    by Charlie — November 4, 2014

  24. St. George Utah
    Lots to do! Great people and many from midwest and so. california. Beautiful landscape. Nothing like Vegas.

    by carol — November 4, 2014

  25. Idahoans-Any comments for Idaho pretty places (Boise, Coeur d’Alene, Sandpoint, etc.)? I would also like to know more about living in Idaho, is this a friendly State for retirement (property tax, cost of living, etc.) or not? Thanks for your comments!

    by looking-4retirement-place — November 5, 2014

  26. Charlie,
    Sounds very appealing! My one concern would be excessive heat and humidity from June thru the end of September. That’s why i’m looking in the mountains. If only.

    by ella — November 5, 2014

  27. Ella, just about anyplace from Florida o Boston will have heat and humidity. Some mitigation comes from being near the coast but that’s why they invented air conditioning. To each his own. Mountains are nice, but get cold in the winter. there was already snow in the North and South Carolina mountains!

    by Charlie — November 5, 2014

  28. Charlie, you’re right, of course! I think i will look into this area. However, another negative would be hurricanes. Yes?

    by ella — November 6, 2014

  29. Ella, Yes there are hurricanes. They can hit anywhere along the eastern seaboard. My daughter had her car flooded out during hurricane Sandy and she lives in Hoboken, NJ! With the weather it is always the roll of the dice. On the Inner banks we are 40 miles from the ocean so any hurricanes that come through get diminished. However, there are no guarantees. I traveled for business for many years nationwide and international. Every place has it’s own set of natural disaster risks. Just pick your poison: Tornadoes in the Midwest, earthquakes and fires in California, volcanoes in Hawaii, Blizzards up north, floods along the Mississippi etc.

    by Charlie — November 6, 2014

  30. Weather: it does seem to becoming more violent almost everywhere.

    Tornadoes are not limited to the midwest. When I moved to Birmingham AL, I causally mentioned to someone who lived there that at least you don’t have tornadoes. She told me (at that time) more people where killed by tornadoes in Jefferson county than any other county in the country. One reason is that they come at night. Now this was back in the mid eighties, I am sure that has changed, but…buyer beware.

    by Elaine — November 8, 2014

  31. I think that weather that comes with advance warning, such as a Blizzard or a Hurricane is tolerable, more so than an EarthQuake or Wildfire that blows up suddenly. It’s all about the opportunity to prepare, hunker down (as we say in Maine during the winter), or board up the windows and drive away, as they do along the east coast during hurricane season.

    by SandyZ — November 9, 2014

  32. Charlie,
    Thanks for the input on the Inner Banks. Much appreciated!

    by ella — November 10, 2014

  33. We have traveled to many areas in the states. Each has a beauty to behold. Gary, my daughter lives in Rawlins, WY. It is windy all year long, and cold in the winter.
    if you all want a mild climate then Grand junction, Co fits that bill. however, I am not promoting it. In the winter, it snows all around us, and makes it hard to get over the passes to go anywhere. We also have a drug problem, especially with the marijuana users. Taxes are 8.8 percent, Gas at the moment is 2.30 a gal. Eastern Wy gets tornadoes and lots of snow, while eastern TN has humidity, and a possible tornado.
    We have considered many places to retire, but don’t want to be clear across the country from our kids.
    The whole thing boils down to what is important to the retiree. There are too many pros and cons to consider. i wish the choice was easy.
    Cheryl- Dec. 15, 2014

    by Cheryl Coverly — December 14, 2014

  34. Cheryl, Grand Junction is always a welcome site when driving east on I70, especially at night! I actually have not been to Colorado since pot became legal there, but I always thought there was a fairly high proportion of stoners on the streets of Colorado cities even before the legalization!!! Rawlins is in the Union Pacific corridor where the weather is worst of Wyoming in my opinion. We’ve lived in Cheyenne and Rock Springs before and can attest to that fact! Driving along I80 in the winter is a crap shoot! We now live in Riverton which is in the Valley of the Winds (and the homeless drunk capitol of Wyoming) and our winters SEEM mild only because most of the snow is scraped off by the mountains before it gets here. I actually like snow, lot’s of snow! I don’t like drunks! Lander or DuBois are close and reasonably priced, and there is less petty crime. Jackson is too expensive but only a three hour drive when the roads are at their worst! We’ve considered some places along the North Platte in East Wyoming, like Torrington or Lingle, but as long as our daughter and grandkids are here, we’ll stay put and take frequent vacations 🙂

    by Gary — December 15, 2014

  35. The main problem with Wyoming,I know I am a native from here,is the one sided politics,which affects everything in the state.Another problem,which has been exasperated the last 20 years,is all the wealthy transplants who have bought up land reducing the locals chances of hunting and fishing access,along with driving up real estate prices .Casper,Cody,Sheridan are examples of this problem. Ig really got bad in Wyoming in the late 1980’s when the states non diversified economy fizzled out and many had to leave to find work,leaving the door wide open for transplants.Myself I went to Alaska to work in those days,even that state has been overrun with rich transplants.At my age I dont have to work anymore,but it sure hurts to see your home state ruined by greed.

    by JB — December 15, 2014

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