These Are The BEST Places to Retire in Connecticut

Published on 27 December 2023 at 11:25

Relocating during retirement can be a smart financial decision to stretch retirement savings. Connecticut is an attractive option for retirees due to its natural beauty, outdoor activities, healthcare system, rich history and cultural scene, and proximity to major metropolitan areas. Additionally, Connecticut offers tax advantages for retirees, with social security benefits not being taxed and a generous exemption for pensions. The presence of reputable companies such as The Hartford Financial Services Group, Cigna Group, and Webster Financial Corporation provides employment opportunities and supports the local economy. Connecticut holds a special place in my heart. I grew up in Connecticut and it truly is a beautiful place. 

Key Takeaways:

  • Connecticut offers a range of retirement destinations with various advantages.
  • Retirees can enjoy Connecticut's natural beauty, outdoor activities, healthcare system, history, and cultural scene.
  • The state provides tax advantages for retirees with exempt social security benefits and pensions.
  • Connecticut's economy benefits from reputable companies that provide job opportunities.

Why Choose Connecticut for Retirement?

Connecticut offers several compelling reasons for retirees to choose it as their retirement destination. The state's natural beauty, including its long coastline, forests, and mountains, provides ample opportunities for outdoor activities such as hiking, fishing, and boating.

Connecticut's healthcare system is highly ranked, with top hospitals and medical centers located throughout the state. Retirees can access quality healthcare services and specialists conveniently, ensuring their well-being during their golden years.

The state's rich history and cultural scene offer retirees access to many museums, art galleries, and theaters. You can indulge in cultural experiences, admire artistic masterpieces, and immerse yourself in the vibrant arts community.

Additionally, Connecticut's advantageous location close to major metropolitan areas like New York City and Boston presents retirees with easy access to a plethora of world-class amenities and entertainment options. You can enjoy Broadway shows, fine dining, shopping, and a vibrant nightlife scene.

Despite the relatively high cost of living, Connecticut offers tax advantages for retirees. Social security benefits are not taxed in the state, and there is a generous exemption for pensions, allowing retirees to maximize their retirement income.

Best Places to Retire in Connecticut

Based on our methodology, we have identified the 9 best places to retire in Connecticut for retirees. Our rankings considered factors such as cost of living, climate, healthcare, safety, transportation, recreational activities, and quality of life. The list is presented in ascending order of the total attainable score. Each of these 9 locations offers unique advantages and caters to the needs and preferences of retirees.


Bristol is a small city with a population of around 60,661. It offers a low crime rate and a strong sense of community, making it an ideal choice for retirees in Connecticut seeking a safe and welcoming environment.

In addition to its community feel, Bristol boasts a lower cost of living compared to many other parts of Connecticut, making it an attractive destination for retirees looking to make the most of their retirement income. This allows retirees to enjoy a comfortable and affordable lifestyle without compromising on quality.

Bristol's location is another factor that contributes to its appeal for retirees. Situated within easy driving distance to major cities like Hartford, New Haven, and Providence, Bristol offers convenient access to urban amenities without the hustle and bustle associated with city living. This makes it an excellent compromise for retirees who want the best of both worlds – a peaceful and close-knit community combined with the convenience of nearby cultural and entertainment offerings.


Norwich is one of the best towns for retirees in Connecticut, offering a combination of rich history, vibrant arts and culture scene, and access to scenic natural landscapes. The city boasts several museums and historic sites, allowing retirees to immerse themselves in its fascinating past.

Located in a picturesque part of Connecticut, Norwich provides retirees with ample opportunities for outdoor recreation. With parks, hiking trails, and lakes nearby, nature enthusiasts can indulge in their favorite activities, from leisurely strolls to adventurous hikes.

For those seeking entertainment and gaming options, Norwich is close to the Mohegan Sun and Foxwoods casinos, which offer a wide range of amenities and activities.

In terms of healthcare, Norwich is well-equipped with facilities such as the Backus Hospital, ensuring retirees have access to quality medical care.

Whether retirees are looking for cultural immersion, outdoor adventures, or reliable healthcare services, Norwich provides a desirable location that combines all these elements for a fulfilling retirement experience.

Southport: A Coastal Village with New England Charm

Southport, located in Fairfield County, Connecticut, is a small coastal village known for its picturesque New England charm, historic homes, and breathtaking views of Long Island Sound. Retirees looking for a serene and scenic retirement destination will find Southport to be an ideal choice.

Beach and Recreation

One of the highlights of Southport is its easy access to the beach. Retirees can enjoy long walks along the shoreline, bask in the sun, or take a refreshing dip in the water. The beach provides serene and peaceful surroundings, perfect for relaxation and rejuvenation.

Additionally, Southport offers a range of recreational opportunities associated with its coastal location. Fishing enthusiasts will find ample spots for a peaceful day by the water, while boating enthusiasts can explore the Long Island Sound and its charming coastal towns.

A Tight-Knit Community

Southport boasts a tight-knit community, where neighbors know and support each other. Retirees will find a warm and welcoming atmosphere, making it easy to establish new friendships and connections. The village hosts a variety of local events and activities, providing retirees with ample opportunities to engage with the community and foster relationships.

Nature and Outdoor Activities

Surrounded by parks and nature preserves, Southport offers retirees the chance to immerse themselves in nature. Explore the stunning trails, witness the vibrant flora and fauna, and enjoy peaceful picnics in the scenic surroundings. Whether it's a leisurely stroll or an adventurous hike, Southport provides plenty of opportunities for outdoor recreation.

Experience the Charm of Southport

For retirees seeking a retirement destination characterized by natural beauty, a strong sense of community, and abundant recreational activities, Southport is a perfect choice. Embrace the idyllic New England charm, enjoy the coastal lifestyle, and create lasting memories in this picturesque village.


Darien is a highly desirable town for retirees in Connecticut. Its convenient location, just 37 miles from New York City, allows retirees to easily access the vibrant cultural attractions, diverse dining options, and world-class shopping of the city.

One of the highlights of Darien is its excellent schools, making it an appealing choice for retirees with grandchildren or those seeking lifelong learning opportunities. The town has a low crime rate, ensuring a safe and secure environment.

Darien boasts beautiful parks and beaches, providing retirees with ample opportunities to enjoy outdoor activities and soak in the natural beauty of the area. Additionally, the town is home to several high-quality medical facilities, including Stamford Hospital and Greenwich Hospital, ensuring excellent healthcare services for retirees.

Overall, Darien offers a well-rounded retirement experience with its proximity to New York City, top-notch educational opportunities, low crime rate, and access to beautiful parks and beaches. It is undoubtedly one of the best towns for retirees in Connecticut.

Riverside: Tranquil and Secure Retirement Haven

Riverside, located in Fairfield County, stands out as one of the best towns for retirees in Connecticut. Renowned for its affluence and picturesque charm, this community offers a tranquil and secure environment for retirees seeking a peaceful retirement. With its natural beauty, top-rated schools, and proximity to New York City, Riverside truly offers the best of both worlds.

Natural Scenery and Outdoor Recreation

Surrounded by stunning natural scenery, Riverside provides retirees with access to beautiful beaches, scenic parks, and invigorating hiking trails. Along the shores of the Long Island Sound, retirees can enjoy breathtaking views and engage in a variety of outdoor activities such as leisurely walks, picnics, and bird-watching. The town's proximity to nature ensures a refreshing and serene retirement experience.

Top-Rated Schools and Educational Opportunities

Riverside boasts a reputation for its exceptional education system and top-rated schools. Retirees who value lifelong learning can take advantage of the numerous educational opportunities available in the town and nearby areas. Whether you're interested in attending lectures, workshops, or community courses, Riverside provides access to intellectual stimulation and personal growth.

Proximity to New York City

Located just a stone's throw away from New York City, Riverside offers retirees easy access to the vibrant cultural scene and world-class amenities that the city has to offer. Retirees can indulge in the finest dining experiences, visit renowned museums and galleries, or catch a Broadway show. The proximity to New York City ensures that retirees can enjoy an exciting city life whenever they desire.

Safe and Sound

Riverside boasts a low crime rate, providing retirees with peace of mind and a sense of security. The town's commitment to safety contributes to a worry-free retirement experience, allowing retirees to fully enjoy their golden years without concerns about personal safety or property security.

For retirees seeking a tranquil and secure retirement haven, Riverside in Fairfield County is an idyllic choice. With its natural beauty, top-rated schools, proximity to New York City, and commitment to safety, Riverside offers retirees a slice of paradise where they can enjoy a blissful retirement lifestyle.

Cos Cob: An Idyllic Retirement Destination in Connecticut

Cos Cob, located in the beautiful southwest corner of Connecticut, is one of the best towns for retirees in Connecticut. This charming town offers a serene and picturesque environment that captivates the hearts of its residents.

One of the highlights of Cos Cob is its abundance of beautiful parks and natural scenery. The town is surrounded by gems like the Mianus River State Park, where retirees can enjoy hiking trails, picnicking spots, and stunning views of the river. Greenwich Point Park, with its sandy beaches and gentle waves, provides the perfect spot for relaxation and enjoying the coastal scenery.

When it comes to safety and security, Cos Cob exceeds expectations. The town boasts a low crime rate, allowing retirees to enjoy peace of mind as they explore this tranquil community.

Another advantage of choosing Cos Cob as a retirement destination is the availability of excellent healthcare facilities and senior services. The town is well-equipped to cater to the healthcare needs of retirees, ensuring they receive top-notch medical care and support.

Points to consider:

  • Beautiful parks and natural scenery
  • Low crime rate, ensuring safety and security
  • Excellent healthcare facilities and senior services

Furthermore, Cos Cob's prime location makes it highly convenient for retirees seeking cultural and entertainment offerings. The town is well-connected to major cities like New York City and Stamford, allowing retirees to easily access a plethora of museums, galleries, theaters, and other attractions. Whether it's a Broadway show or a fine dining experience, retirees in Cos Cob have an array of options within reach.

Cos Cob, with its natural beauty, safety, healthcare, and proximity to cultural centers, has all the essential elements retirees seek in an ideal retirement town. Consider Cos Cob as a top choice when planning your retirement in Connecticut.


Hartford, the capital city of Connecticut, offers retirees a variety of amenities and attractions. With its proximity to Boston, New York City, and other major cities, Hartford provides easy access to cultural and entertainment options. The city has a rich history and is home to several museums, theaters, and other cultural institutions. Hartford has four distinct seasons and offers a range of recreational activities for retirees to enjoy.


Torrington is a small city located in the tranquil Litchfield Hills region of Connecticut. With a population of over 35,300, Torrington offers a charming small-town ambiance that is perfect for retirees seeking a peaceful and close-knit community.

One of the major attractions of Torrington is its relatively affordable cost of living compared to other parts of Connecticut. Retirees can enjoy a comfortable lifestyle while stretching their retirement savings further.

In addition to its affordability, Torrington boasts a stunning natural setting. The Litchfield Hills region provides a picturesque backdrop, offering opportunities for outdoor recreation such as hiking, fishing, and skiing. Whether you prefer a leisurely stroll through beautiful parks or an adrenaline-pumping adventure, Torrington has something for every outdoor enthusiast. My uncle currently lives here and he is a retired USPS employee. My Grandpa lived here as well and he was a retiree CEO of a businees.

Vibrant Arts Scene

For retirees with an appreciation for the arts, Torrington does not disappoint. The city is blessed with a vibrant arts scene, with numerous galleries, theaters, and museums to explore. Immerse yourself in local talent, enjoy live performances, and appreciate the creativity that thrives within the community.

Weatogue: A Tranquil Haven for Retirees in Connecticut

Good ol Weatogue aka West Simsbury. This is where I hail from! I've spent my formative years living here and have fond memories of West Simsbury. The crime rate is next to none it's a sleepy little place. Weatogue, a charming village nestled amidst majestic mountains, lush parks, and serene nature reserves, is a hidden gem for retirees seeking an idyllic and peaceful lifestyle in Connecticut. This picturesque town offers a perfect escape from the hustle and bustle of city life, providing a slower-paced environment for you to savor each moment of your retirement.

One of the primary attractions of Weatogue is its abundance of outdoor activities that cater to nature enthusiasts. The surrounding mountains offer scenic hiking trails, giving you the opportunity to immerse yourself in the beauty of the Connecticut landscape. You can also enjoy leisurely bike rides and peaceful fishing trips in the nearby parks and lakes. Weatogue truly embraces the spirit of outdoor adventure, ensuring that you will never run out of opportunities to explore and connect with nature.

For retirees prioritizing their healthcare needs, Weatogue has several esteemed medical centers and hospitals that provide exceptional care. You can enjoy peace of mind knowing that you have access to top-notch medical services within close proximity to your home. The town's commitment to providing excellent healthcare ensures that you can enjoy your retirement years with confidence and security.

Immerse yourself in the tranquility of Weatogue and discover a retirement haven like no other. This scenic village combines pristine natural beauty, a slower-paced lifestyle, and convenient access to quality healthcare, making it one of the best towns for retirees in Connecticut. Embrace this opportunity to create a fulfilling and serene retirement experience in Weatogue.


Connecticut offers an array of appealing retirement destinations that boast unique advantages. Whether you prefer the close-knit community of small cities or the captivating views of coastal villages, the state has something to suit every retiree. Its natural beauty, abundant outdoor recreational activities, high-quality healthcare system, and proximity to major metropolitan areas make it an enticing choice. Moreover, Connecticut's tax advantages for retirees further enhance its appeal as a preferred retirement spot. As you plan for your retirement, consider these top retirement havens in Connecticut to make the most of your golden years.


Why should I choose Connecticut for retirement?

Connecticut offers a range of retirement destinations with natural beauty, outdoor activities, a high-quality healthcare system, rich history and cultural scene, proximity to major metropolitan areas, and tax advantages for retirees.

What are the best places to retire in Connecticut?

Based on our rankings, some of the best places to retire in Connecticut include Bristol, Norwich, Southport, Darien, Riverside, Cos Cob, Hartford, Torrington, and Weatogue.

What makes Bristol an ideal retirement spot?

Bristol is a small city known for its low crime rate, strong sense of community, affordability, and convenient location near major cities.

Why should I consider retiring in Norwich?

Norwich is known for its rich history, vibrant arts and culture scene, scenic location, access to outdoor activities, and healthcare facilities.

What does Southport offer as a retirement destination?

Southport is a small coastal village with picturesque views, historic charm, access to the beach, a tight-knit community, and abundant recreational opportunities.

What advantages does Darien offer for retirees?

Darien is located near New York City, known for its excellent schools, low crime rate, beautiful parks and beaches, and high-quality medical facilities.

What makes Riverside an attractive retirement community?

Riverside offers a tranquil and secure environment, natural scenery, proximity to New York City, low crime rate, and access to beautiful beaches, parks, and hiking trails.

What does Cos Cob have to offer retirees?

Cos Cob is known for its beautiful parks, natural scenery, low crime rate, excellent healthcare facilities, senior services, and convenient access to cultural and entertainment offerings in nearby cities.

Why should I consider retiring in Hartford?

Hartford offers retirees a variety of amenities, attractions, rich history, cultural institutions, access to major cities, varied recreational activities, and a range of healthcare options.

What makes Torrington a good retirement location?

Torrington is a small city with an affordable cost of living, a scenic location in the Litchfield Hills, access to outdoor recreation, and a vibrant arts scene.

What does Weatogue offer as a retirement haven?

Weatogue is a small village surrounded by mountains, parks, and nature reserves. It offers a tranquil environment, outdoor activities, and top-notch medical care.

What are the best retirement destinations in Connecticut?

Connecticut offers a variety of attractive retirement destinations with natural beauty, outdoor activities, quality healthcare, and proximity to major metropolitan areas. Consider Bristol, Norwich, Southport, Darien, Riverside, Cos Cob, Hartford, Torrington, and Weatogue when planning your retirement.

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