Editor’s note: This article offers general ideas for a retirement scouting trip.
Many folks visit a community that appeals to them and fall in love. But the details that form their daily lives when they’re retired were hidden by the experience of being on vacation. It’s best to live in town for a few uneventful days to get a handle on what’s important to you.
1. Belfast, Maine
Belfast’s working harbor and compact, walkable downtown are appealing.
Its community hospital, MaineHealth Waldo Hospital, provides emergency and other services.
However, older housing stock, insurance, heating bills and coping with cold, rainy and icy weather are considerations after touristy summer ends.
2. Lewes, Delaware
Lewes offers historic areas, beaches and a walkable downtown.
Beebe Healthcare provides an emergency room open 24 hours a day and other services.
Flood and wind insurance, summer crowds and traffic are factors.
3. Abingdon, Virginia
Abingdon has a brick-lined downtown backed by the Appalachians.
Johnston Memorial Hospital has an emergency room and other services.
Long drives to larger cities and poor weather in the mountains are considerations. So are hills on which to build or buy.
4. Brevard, North Carolina
Brevard’s downtown is appealing, but consider how you’ll fare on the mountain roads leading to homes farther out of town.
Transylvania Regional Hospital, a 25-bed hospital, has an emergency department along with orthopedic and other services.
How is drainage, internet connection, access during bad weather? Steep driveways?
5. Fairhope, Alabama
Fairhope’s bay views, live oaks and walkable streets are appealing, but August heat can be oppressive. What about insurance?
Thomas Hospital offers emergency, critical care, orthopedic and other services.
Get quotes for homeowners insurance, wind, flood, etc., once you’ve narrowed it down to a handful of houses.
6. Oxford, Mississippi
Oxford has a major university and an appealing walkable square.
Baptist Memorial Hospital-North Mississippi has an ER plus heart, cancer, rehabilitation and other services. Read more: retirement communities that buyers often miss.
Consider game-day traffic, parking, noise, summer heat and humidity. How do nearby short-term rentals affect the neighborhood during busy times?
7. Decorah, Iowa
Decorah has a traditional downtown, nearby limestone bluffs and trails.
WinnMed has an ER and offers urgent care, inpatient, rehabilitation and other services. Read more: scenic driving plan.
Iowa exempts qualifying retirement income for many who are 55 or older. Check your eligibility, and consider heating bills, shoveling, etc.
8. Traverse City, Michigan
Traverse City is a small city with easy access to the bay.
Munson Medical Center is a referral hospital for northern Michigan. Read more: scenic train and road trips.
It’s cold, windy and snowy in the winter, so check heating bills and how you’ll handle icy roads. Summers can be busy with tourists.
9. Spearfish, South Dakota
Spearfish is close to the northern Black Hills.
Monument Health Spearfish Hospital offers emergency care, a host of specialties, intensive care and surgical services. Read more: weekday scenic drives.
There’s no state individual income tax in South Dakota. Consider insurance against hail, access during inclement weather, wildfire evacuation and distance to specialists.
10. Fredericksburg, Texas
Fredericksburg’s historic downtown caters to tourists, but there’s plenty to do year-round.
Methodist Hospital Hill Country has an ER plus heart, cancer, rehabilitation, orthopedic and other services. Read more: Texas retirement communities.
Texas does not charge a personal income tax. Property taxes, insurance, cooling bills and water bills can still be pricey. Check how short-term rentals affect life around a potential home.
11. Silver City, New Mexico
Silver City’s high-desert downtown is close to outdoor recreation on public lands. Summers are warm and nights can be chilly; the air is dry.
Gila Regional Medical Center is a 25-bed critical access hospital that provides emergency care, cancer care, surgery, imaging and other services. Read more: overlooked western stops.
Consider access during inclement weather, high elevation and distance to specialists.
12. Prescott, Arizona
Prescott has a compact, walkable historic downtown on high terrain.
Dignity Health Yavapai Regional Medical Center’s Prescott campus offers a range of services. Check the ones you need.
Consider how to get around during inclement weather, distance to specialists, evacuation in case of wildfire, insurance, etc.
13. Sandpoint, Idaho
Sandpoint has a compact downtown and is nestled between lake and mountain.
Bonner General Health, a 25-bed critical access hospital, offers emergency care, cancer care, orthopedic care, imaging, rehabilitation and other services. Read more: slow scenic-driving plan.
Consider how to get around during inclement weather, shoveling or plowing costs, wildfire coverage and travel for specialist care in larger cities such as Coeur d’Alene or Spokane.
14. Port Townsend, Washington
Port Townsend has an appealing Victorian downtown and access to the water.
Jefferson Healthcare is a critical access hospital that offers emergency care, surgery, rehabilitation and other services. Read more: coastal small towns worth a slow drive.
There’s currently no broad individual income tax in Washington, with a new tax on income above $1 million scheduled for 2028. Consider weather access, wind, earthquake readiness and whether your regular trips rely on a ferry.
15. Astoria, Oregon
Astoria’s riverfront offers river views with the feel of a working port.
Columbia Memorial Hospital offers emergency care, heart care, critical care, surgery and other services. Read more: historic places worth the trip.
Social Security isn’t taxed in Oregon; other forms of retirement income may be taxed. Check for adequate drainage on hillside lots and research property insurance and heating bills.
Make the Scouting Visit Ordinary
During your visit, test-drive the ordinary parts of town living. Check healthcare and appointment availability, shop for groceries, get a haircut and visit places you’d use regularly. Talk to an insurance agent and consider renting in a neighborhood you could afford. Try your usual routes by day and after dark when it’s safe.
Consider staying longer than just a weekend. Make these errands before making an offer on a house, then visit again during the community’s least-desirable season. See if you can cope with the weather without the excitement of a vacation.
Sources
Primary and official sources checked on August 28, 2026:
- Belfast: MaineHealth Waldo Hospital
- Lewes: Beebe Healthcare, Margaret H. Rollins Lewes Campus
- Abingdon: Ballad Health, Johnston Memorial Hospital
- Brevard: Transylvania Regional Hospital
- Fairhope: Infirmary Health, Thomas Hospital
- Oxford: Baptist Memorial Hospital-North Mississippi
- Decorah: WinnMed hospital and services
- Traverse City: Munson Medical Center
- Spearfish: Monument Health Spearfish Hospital
- Fredericksburg: Methodist Hospital Hill Country
- Silver City: Gila Regional Medical Center
- Prescott: Dignity Health Yavapai Regional Medical Center
- Sandpoint: Bonner General Health
- Port Townsend: Jefferson Healthcare
- Astoria: Columbia Memorial Hospital
- Retirement income: Iowa Department of Revenue individual income tax provisions
- State tax structure: South Dakota Department of Revenue individual tax information
- State tax structure: Texas Comptroller guidance
- State tax structure: Washington Department of Revenue income tax FAQ
- Retirement income: Oregon Department of Revenue personal income tax guidance
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