October 28, 2014 — 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 Topretirements.com, 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, 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.
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, 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!
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