Thinking about retiring to Vermont?
I once shared that dream of peaceful country roads and village greens.
Then I ran the numbers.
Some Vermont towns will deplete your nest egg faster than you can pronounce “Winooski.”
Winter isolation, limited services, and surprising costs create retirement challenges the tourism board doesn’t advertise.
The state’s natural beauty remains constant, but your retirement satisfaction in these 20 towns might melt away faster than April snow.
1. Fair Haven, Vermont
Fair Haven sits at the western edge of Vermont, bordering New York. This small town might look charming at first glance, but retirees face significant challenges here.
The town struggles with limited healthcare options, forcing seniors to travel for specialized medical care.
Winter months can be particularly harsh, with heavy snowfall and limited public transportation making it difficult for older residents to get around.
Why It’s On This List: Fair Haven tops our list due to its combination of high property taxes, limited senior services, and isolation during winter months.
2. West Brattleboro, Vermont
West Brattleboro might offer beautiful scenery, but retirement here comes with serious financial concerns. The median income is only $40,446, with a poverty rate approaching 20%.
The unemployment rate sits at 4.9%, which doesn’t help the overall economic situation.
While you can enjoy the nearby Green Mountain National Forest, the financial strain might overshadow the natural beauty.
Why It’s On This List: The combination of low median income, high poverty rates, and limited economic opportunities makes West Brattleboro a challenging place for retirees on fixed incomes.
3. Brattleboro, Vermont
Brattleboro proper faces even more severe economic challenges than its western counterpart. The unemployment rate here is a concerning 9.2%.
The median income of $42,776 isn’t enough to offset the high cost of living that plagues much of Vermont.
But here’s the deal: while the town has cultural offerings, the financial strain can make retirement here difficult.
Why It’s On This List: High unemployment combined with modest incomes makes it difficult for retirees to maintain financial stability in Brattleboro.
4. Morrisville, Vermont
Morrisville made the list of challenging places to live in Vermont overall, and the same issues affect retirees. The town struggles with economic stability.
Winter accessibility becomes a major concern for seniors, with snow removal services being costly and sometimes hard to find.
You’re better off considering the limited healthcare options before settling here for your retirement years.
Why It’s On This List: Limited senior services, healthcare access issues, and harsh winters make daily life challenging for retirees in Morrisville.
5. Springfield, Vermont
Springfield faces economic challenges that directly impact retirees. The town has struggled to maintain its economic base over recent years.
Housing costs remain high relative to income levels, creating a financial squeeze for those on fixed retirement incomes.
That’s why many retirees find their savings depleting faster than expected when living in Springfield.
Why It’s On This List: The combination of economic decline and relatively high housing costs creates a difficult financial environment for retirees.
6. Bennington, Vermont
Bennington offers historic charm but presents practical challenges for retirees. The town’s healthcare facilities are limited compared to more populated areas.
Property taxes here, like much of Vermont, rank among the highest in the nation.
Winter isolation can become a serious concern, especially for older residents who may have mobility issues.
Why It’s On This List: High property taxes combined with limited healthcare options make Bennington less than ideal for retirement living.
7. West Rutland, Vermont
West Rutland struggles with providing adequate services for its aging population. The town has limited public transportation options.
Healthcare specialists are often a significant drive away, creating challenges for regular appointments.
I made a classic mistake thinking small town charm would outweigh practical needs, but retirees need reliable access to services.
Why It’s On This List: The lack of senior-focused amenities and services makes daily life unnecessarily challenging for retirees.
8. Newport, Vermont
Newport sits near the Canadian border, making it one of the coldest spots in Vermont. Winter temperatures regularly drop below zero, creating hazardous conditions for seniors.
The remote location means limited access to specialized healthcare services.
The job market is small, which affects retirees looking for part-time work to supplement their income.
Why It’s On This List: Extreme winters combined with isolation from major healthcare centers makes Newport particularly challenging for retirement living.
9. Milton, Vermont
Milton faces challenges with affordability that hit retirees particularly hard. Housing costs remain high while services for seniors are limited.
The town’s location means residents often need to travel for specialized medical care.
Want me to explain why this matters? For retirees with mobility issues or those who no longer drive, this creates significant barriers to healthcare access.
Why It’s On This List: The combination of high living costs and limited senior services makes Milton difficult for retirees on fixed incomes.
10. White River Junction, Vermont
White River Junction serves as a transportation hub but lacks comprehensive services for seniors. The cost of living remains high compared to retirement income.
Winter weather creates significant challenges, with snow removal and heating costs becoming major expenses.
But here’s the catch: while it’s close to Dartmouth-Hitchcock Medical Center, daily living expenses can quickly deplete retirement savings.
Why It’s On This List: Despite good medical facilities nearby, the high cost of living and harsh winters make White River Junction challenging for retirees.
11. Bellows Falls, Vermont
Bellows Falls sits along the Connecticut River with historic charm, but retirement here comes with challenges. The town struggles with economic stability and limited growth.
The median household income hovers around $41,000, making it difficult for retirees on fixed incomes.
That’s why many seniors find themselves financially stretched when facing Vermont’s high heating costs and property taxes.
Why It’s On This List: Economic stagnation combined with high living costs creates financial pressure for retirees in Bellows Falls.
12. St. Albans, Vermont
St. Albans offers small-town living but lacks comprehensive services for seniors. The town has limited specialized healthcare options.
Winter weather is particularly harsh, with Lake Champlain’s influence creating heavy snowfall.
But here’s the deal: while the downtown has charm, the practical challenges of daily living can overwhelm retirees.
Why It’s On This List: Limited senior services combined with severe winters make St. Albans a difficult choice for retirement living.
13. Swanton, Vermont
Swanton’s location near the Canadian border means brutally cold winters. Temperatures can drop to -20°F, creating dangerous conditions for seniors.
The town has limited public transportation options, making it difficult for non-driving retirees.
You’re better off considering these practical limitations before being charmed by the rural setting.
Why It’s On This List: Extreme winter conditions combined with isolation from services creates significant challenges for retirees in Swanton.
14. Lyndonville, Vermont
Lyndonville faces economic challenges that directly impact retirees. The job market is limited for those seeking part-time work.
Healthcare options are restricted, often requiring travel to larger towns for specialized care.
I made a classic mistake assuming small towns always have lower costs, but Vermont’s rural areas often have surprisingly high living expenses.
Why It’s On This List: Limited economic opportunities combined with healthcare access issues make Lyndonville challenging for retirees.
15. Windsor, Vermont
Windsor claims to be the “Birthplace of Vermont” but struggles to provide comprehensive services for seniors. The town has limited specialized healthcare facilities.
Property taxes remain high, creating financial pressure for those on fixed incomes.
Winter accessibility becomes a major concern, with snow and ice making travel difficult for older residents.
Why It’s On This List: The combination of high taxes and limited services creates daily challenges for retirees in Windsor.
16. Island Pond, Vermont
Island Pond sits in Vermont’s “Northeast Kingdom,” known for its natural beauty and extreme isolation. The town is over 30 miles from the nearest hospital.
Winter temperatures regularly drop below zero, with snowfall often exceeding 100 inches annually.
Want me to explain why this matters? For seniors with health concerns, this isolation can be not just inconvenient but potentially dangerous.
Why It’s On This List: Extreme isolation from healthcare services makes Island Pond particularly challenging for retirement living.
17. Enosburg Falls, Vermont
Enosburg Falls struggles with providing adequate services for its aging population. The town has limited public transportation options.
Healthcare specialists are often a significant drive away, creating challenges for regular appointments.
But here’s the catch: while housing costs might be lower than some Vermont towns, the practical limitations can outweigh the financial benefits.
Why It’s On This List: Limited access to healthcare and services makes Enosburg Falls difficult for retirees who value convenience and accessibility.
18. Richford, Vermont
Richford sits directly on the Canadian border, making it one of Vermont’s most remote towns. The nearest hospital is over 20 miles away.
Winter weather is severe, with roads sometimes becoming impassable during heavy snowstorms.
That’s why many retirees find themselves isolated during Vermont’s long winters, creating both practical and emotional challenges.
Why It’s On This List: Extreme isolation and harsh winters create significant barriers to comfortable retirement living in Richford.
19. North Troy, Vermont
North Troy faces significant challenges with its remote location and limited services. The town has minimal shopping options for daily necessities.
Healthcare access requires travel, with specialized care often more than an hour away.
I made a classic mistake thinking rural charm would compensate for practical needs, but retirees need reliable access to services.
Why It’s On This List: The combination of isolation and limited services makes North Troy particularly challenging for seniors.
20. Canaan, Vermont
Canaan represents Vermont’s most northeastern town, bordering both New Hampshire and Quebec. This extreme location means serious isolation from services.
The nearest major hospital is over 50 miles away, creating significant healthcare access issues.
You’re better off considering these practical limitations before being attracted to the lower housing costs in this remote corner of Vermont.
Why It’s On This List: Extreme isolation from healthcare and services makes Canaan perhaps the most challenging Vermont location for retirees seeking convenience and accessibility.