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10 Undiscovered Places to Retire

Category: Best Retirement Towns and States

April 20, 2021 — Our mission here at Topretirements is to find great places to retire, so we are always on the lookout for undiscovered gems. Today we are going to spill the beans about some undiscovered retirement towns that you might not have heard about before. See end of article for more ideas for underappreciated places to retire.

By definition, most of these places are small.

Boca Grande, Florida. This small, upscale and beautiful residential community is located on Gasparilla Island between Fort Myers and Sarasota. It is home to many retirees and seasonal residents with an average age of 66. The Boca Grande Pass is the deepest natural pass in Florida, and is considered to be the world’s best tarpon fishing spot. That makes the small town not only a tourist destination, but a haven for fishermen. The seven mile island also offers white sand beaches and a quaint downtown and restaurants, but you won’t find any high rises, traffic lights, grocery stores, or gas stations.

Leonardtown, MD. A very small town, it is found in a pastoral section of Maryland between the mouth of the Potomac River and Chesapeake Bay at the southern end of a large peninsula. This area was slow to be developed because of its distance from any city and the bridges that had to be crossed to get here. On the way into town one drives past the modest farms of an old Mennonite community to the northwest, along with occasional horse and buggies. Growth is now happening at a rapid rate, but the community is trying to exert some control over the loss of farmland that would be devastating to the charm of the area. Its downtown near an inlet of the Potomac features the county courthouse, a handsome square, distinguished old stores, and old wharf .

Salida, Colorado. The nearby Monarch Ski Area is a big attraction, as are the areas mountain biking, hiking, and river rafting. Monarch Mountain looms over the town on one sie, and the Arkansas River on another.  This friendly town combines a bit of a bohemian atmosphere with a working class center. The town is working to enhance pedestrian access to the town.

Tubac, Arizona is an ancient Spanish presidio, or fort, that is now a working artists’ community. Tubac was one of the first stops on the Camino Real, the Royal Road from Mexico to its settlements in California. This community in the high desert of Arizona is extremely scenic and offers exceptional recreational opportunities. The streets of the town are lined with old adobe homes and many interesting shops. The Tubac Festival of the Arts is an event not to be missed.

Scaneatelese, New York. in the Finger Lake region, Skaneateles (SKAN-ee-AT-las) is a small, town on the north end of Skaneateles Lake, with a population of about 2,500 residents.The name comes from the Iroquois word for “long lake, and is regarded as one of the prettiest villages within the Finger Lakes. Its quaint downtown offers a toy shop, a chocolate shop, unique stores, bakeries, art galleries, pubs and a wine bar. The clear blue lake provides recreation activities

Westerly, Rhode Island is  near the Connecticut border. It is very popular with tourists because of the wonderful ponds and beaches in the area.  Its economy was once centered on the local granite quarries.The downtown is especially beautiful with classic buildings, churches, and library. The town includes Watch Hill, a watering hole for New York’s elite. Misquamicut State Beach is one of the finest public beaches anywhere in the country.

Leavenworth, Washington. This small town at the base of the Cascade Mountains is very near the center of the state.  In the 1960’s the town leaders decided to capitalize on its backdrop of the alpine hills and turn the town into a tourist destination.  Using Solvang, California, as their inspiration, they completely renovated the downtown area and transformed it into a Bavarian village, complete with many festivals, to draw revelers into the town.  The idea worked! 

Solvang, California.  in the Santa Ynez mountains of Southern California. Solvang, which is Danish for “Sunny fields”, is about 35 minutes inland from coastal Santa Barbara. Nearby towns include Lompoc, Buellton, Ballard, and Los Olivos.  The area  was made famous when “Sideways”, a dark movie about 2 wine-loving bad boys, was filmed here.  Several local wineries and restaurants were depicted  in the movie. The town itself was founded by Danish settlers. It still has a kitschy Denmark meets Heidelberg feel, but the overall effect is pleasant.

Red Wing, Minnesota. Red Wing has a strong and beautiful downtown in the Mississippi River Valley. It also has an impressive economic base as well as the nearby Treasure Island Resort and Casino. It brims with historic charm, complemented by interesting shops and restaurants. Red Wing is on the National Trust for Historic Preservation’s 2008 distinctive destinations list because of its “impressive architecture and enviable natural environment. Sure, it is cold here in winter, so it makes an excellent spot for snowbirds to make as their summer quarters.

Mount Dora, Florida.  This central Florida lakefront community is nestled in gentle hills and orange groves. With an elevation of 184 feet it is one of the higher communities in Florida, making it Florida’s equivalent of a mountain top town! It features active shopping, excellent antiquing, a rich cultural life, and recreation. Many festivals and community events attract residents and tourists.

Bottom line.

These relatively undiscovered towns are definitely “best places to retire” material. They are all relatively small and quite walkable. But we want to know, what other towns should be on this list? Please add them and any other suggestions in the Comments section below.

For further reading:

Posted by Admin on April 19th, 2021


  1. I have been to many of the places mentioned in the article. All I can say is that there is a reason why they are still “undiscovered.” Vacations okay; to living there, well….

    by Roland — April 20, 2021

  2. We lived in Westerly for 6 years and LOVED IT! The photo is of the the library where we spent a lot of time. The town beach is great – with a pavilion and plenty of room. The town is practically equal distance to NYC and Boston plus easy access to New London, Hartford and Providence. Its right on the Amtrak line and the Providence airport is 45 mins. It was a welcoming place where they cherish family and their children. We were close to going back there but ultimately decided on Maine due to the better Parkinsons medical support.

    by HEF — April 20, 2021

  3. I would second (or, more precisely, third) the recommendation for Westerly. Beaches with rolling surf, the gorgeous Watch Hill and its harbor, the proximity to Providence, Boston and New York. I great central starting point if you enjoy weekend trips — Main, Martha’s Vineyard, Nantucket, Cape Cod, the unparalleled foliage of the northern New England States, and, of course, less than an hour from Newport, one of the most glorious cities in this country as far as this former sailboat owner is concerned.

    by Ed LaFreniere — April 21, 2021

  4. Roland is right. Most people nearing or at retirement age almost exclusively want a new location to have quality health care. I am suspicious that any of those listed are within a reasonable drive of a quality medical center. With aging comes health issues— diabetes, hypertension, knees and hips needing replaced, cardiovascular disease, etc etc. It’s more that sunsets and golf courses that the majority are seeking.
    A lot of the info on this site might be on target for those retiring in their 50s. Not so much for the >65 crowd.
    I would suggest one free source is the site, which lets you compare hospitals and providers, dialysis facilities, etc. It may not be the final word, but one can get an idea of how a center ranks on categories the government tracks– effective care, complications, etc. Best to do the homework when you think about all the things you will need to access if you pick up to move. I lived in the SW once and it was beautiful. I could find a physic or a plastic surgeon on every corner but finding a good internist was next to impossible. Just sayin’……

    by B Dodson — April 21, 2021

  5. Hef, Westerly is a lovely town, but a distance to high quality health care. Most people who live there drive to Yale New Haven. Nobody in their right mind would go to Westerly Hospital or South County Hospital. I don’t know that Maine is any closer to a top rated hospital? I suppose people in Southern Maine could drive a few hours to Boston. I chose a small coastal college town about an 60 miles south of Boston, but still hard to find quality health care in RI.

    B. Dodson, thanks for the website.

    by Maimi — April 23, 2021

  6. Mt Dora, FL is a northern suburb of Orlando so proximity to great air connections at MCO or budget links at Sanford’s SFB are easy, also close to Canaveral National Seashore. Healthcare options are plentiful.

    by kw — May 1, 2021

  7. I lived in Orlando for six years and visited Mt. Dora on a number of occasions. Although it could be considered suburban, I found it to have a very charming small-town feel. The downtown is very attractive.

    by Clyde — May 2, 2021

  8. The two most important things to consider in a retirement location for me is: Quality Health care nearby.
    And this is why we have chosen to live 60 miles from Boston, Ma where the best medical care in the world is available. The other important thing that is NOT available here in Massachusetts, No State Tax. People with a substantial portfolio (bank account) will end up paying the State for the priviledge of living here. Many people have moved north over the State line to New Hampshire which has no State Tax and happily avoid paying it. Many Rhode Islanders make Florida their place of residency to avoid paying their State Income taxes. Be informed before making any decisions concerning where to move in retirement.

    by Shirley — May 21, 2021

  9. Shirley,
    May I ask what town you are living in in the Boston area? We are also are looking near Boston and wanting to learn everything we can about that area. Especially south west of the city. Would like to have close proximity to Rhode Island and the Cape as well.

    by Cindy — May 22, 2021

  10. Cindy-

    I live an hour from Boston in Rhode Island on the west side of Narragansett Bay south of Pawtuxet Cove in the Gaspee’ Plateau area of Warwick overlooking Narragansett Bay and I LOVE it! Friendly neighbors, great colleges and universities, culture, proximity to good transportation hubs (air, train, ferry, bus) and access to excellent medical care. My home is not fancy or large but older with much charm. I grew up in the northern Midwest but scholarships to grad school sent me East and I have moved many times, but this place is my wonderful home. Best wishes in your search! If I can be more helpful, feel free to be in touch!

    by Barb — May 23, 2021

  11. I’d look at Franklin ma, Milford ma, Foxboro ma, and No. Attleboro ma to start

    by Gail — May 23, 2021

  12. Thank you Barb and Gail. Will look into the areas you suggested.

    by Cindy — May 24, 2021

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