8 Charming Connecticut Communities To Retire Around Bridgeport

When one thinks of Connecticut, several things come to mind: affluence, commuting to New York City, and, yes, cold winters. However, the United States Northeast has long been overlooked for its advantages as a retirement destination. This is especially true around Bridgeport, Connecticut’s largest city, where small, senior-friendly towns with excellent amenities, affordable living, and easy access to top healthcare facilities make for ideal retirement spots.

Milford, Connecticut

Starting with the largest and arguably most picturesque city on the list, Milford is a coastal city of 50,000, primed as a playground for retirees who don't want to kick their feet up and take it easy. Accessible by train, highway, or boat, you won't find an easier community to come and go as you please. Just a short drive or train ride southwest of Bridgeport, Milford is a coastal gem primed for retirees who want a balance of relaxation and activity.

Take part in the Oyster Festival every third week in August and enjoy listening to such bands as Joan Jett, Marshall Tucker Band, or Soul Asylum. You can enjoy walking the beach since Milford has over 14 miles of shoreline, more than any town in the state.

Avon, Connecticut

For retirees looking for a quiet, affordable community with quick access to a larger city nearby, about an hour from Bridgeport, Avon provides retirees with peaceful suburban living while keeping them within easy reach of top-tier healthcare and amenities. Because West Hartford is only seven miles away, the Hartford Hospital, one of the best hospitals in the country, is just a short drive away. Avon boasts a strong healthcare industry, with Avon Health Center Inc. and Apple Healthcare Inc. ranking among the town’s top employers.

Known for its historical background, the Pine Grove School House has been transformed into a museum open to the public. The Blue Fox Run Golf Course is popular with the retired.

Middletown, Connecticut

When it comes to arts and culture, Middletown is a surprising option for retirees. Enjoy visual and performing arts from Wesleyan University or the well-known youth theater group, Oddfellows Playhouse.

See a different view of Middletown while taking the Katharine Cruises along the Connecticut River or explore the Mattabesett Trail that traverses the Metacomet Ridge. The Middlesex Historical Society is a fun local museum preserving regional history. Also, the Middletown Senior and Community Center is available to residents 60 years of age and older.

Mystic, Connecticut

If you aim to be in the middle of the action, Mystic is the place for you. One of Connecticut's top tourism destinations, there is never a shortage of activities. Mystic isn't an actual town; it is a census-designated place and village in Groton and Stonington. But the area will have you feeling New England vibes.

Enjoy the area's beauty from the Mystic Bridge Cultural District, The Mystic Seaport Museum, or the Mystic Aquarium. The area is home to a couple of first-class retirement living centers, like StoneRidge or Masonicare, as living options.

Southbury, Connecticut

Southbury is known for its strong combination of a rural lifestyle and bustling city amenities. Compared to its smaller neighbors, Oxford and Old Saybrook, Southbury has abundant shopping, recreation, and community events.

Do you want to get back to nature? Southbury has three state parks: Kettletown State Park (south of Southbury), George C. Waldo State Park (west of Southbury), and Southford Falls State Park (southeast of Southbury).

However, the strength of Southbury is its retirement village, Heritage Village, which is one of New England's largest retirement communities.

Madison, Connecticut

Situated on the Connecticut shoreline midway between Boston and New York City, with a direct connection to Interstate 95 and the Shore Line East Train Station as public transportation, Madison has closer access to world-class cities than most retirement communities.

With a population around 17,000, Madison has a percentage of retirees age 65 or older at approximately 14%, and a median household income of $87,000. Enjoy a surprising robust beach community, with East Wharf and West Wharf Beach on Wharf Road, and The Surf Club encompassing 45 acres on Long Island Sound with bocce courts and horseshoe pits available for recreation.

Old Saybrook, Connecticut

Located where the Long Island Sound and the Connecticut River meet is the town of Old Saybrook, a waterfront hideaway that is the perfect option for a retiree looking to blend the charm of the Northeast right on the water.

Cultural art enthusiasts will feel at home retiring to this small Connecticut town of just over 10,000 people. One of the most famed actresses on the silver screen, Katharine Hepburn, is honored here with the Katharine Hepburn Cultural Arts Center and Museum. You'll find a 285-seat theater to enjoy arts programming over 300 days out of the year.

The retirement population percentage is just under 15%, while the median household income is north of $80,000. The Old Saybrook train station was rebuilt in 2002 and provides daily service to Boston and New York.

Oxford, Connecticut

For those who want a quieter, rural retirement within a 40-minute drive of Bridgeport, Oxford’s New England charm and proximity to New Haven’s healthcare facilities make it an attractive option. With a population of just over 12,000, Oxford is located in a part of Connecticut known for its Quaker Farms. Here, you can visit the Quarry Walk, a village-style atmosphere encompassing shops, dining options, and holding many community activities throughout the year. Perhaps, channeling your inner cowboy is what you desire, feel free to stop at Mustang Meadow, a family-owned and operated horseback riding barn within Oxford's town limits, where you can enjoy 144 acres of pastures, bridges, creeks and woods that are accessible for even the most novice rider.

You need not worry about additional amenities since Oxford is only 15 miles northwest of New Haven, where you can take advantage of first-class healthcare facilities.

Connecticut's Retirement Havens Near Bridgeport

While the Northeast isn't as well known for its retirement communities as more traditional locales, like Florida or Arizona, you can see retirement has a new meaning in Connecticut. With unrivaled historical charm, access to world-famous cities, and some of the best healthcare facilities in the country, these small Connecticut towns will have retirees thinking more about leaf-watching in the fall than strolling down a beach.