20 Great Places to Retire

When the time comes, you'll know it. But you may not know where to spend it. Here are some suggestions.


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You may have far-flung plans for your retirement, or you may plan on staying right where you are. But for a growing number of aging baby boomers in Connecticut, the plan is to get out of the house they're in and into a smaller place in a pleasant location not too far from family and friends. That's why during the last 10 years or so there's been an explosion of new housing, and even new communities, for "active adults" over the age of 55 in the state.

With such a huge trend staring us in the face, we decided to get on board with a look at some of the top retirement towns in Connecticut. This is not a scientific survey, but in most cases it does take into account things like cultural amenities, public safety, proximity to medical centers and the availability of appropriate housing. In the range of towns we've selected, we've tried to find something for everyone. But at the same time, we understand that it's possible to experience a perfectly enjoyable retirement in any of the state's 169 towns. Ultimately, it all depends on you, your situation, and your likes and dislikes.

For those who might be looking, however, here are some places to consider.

Shoreline Twins: Madison & Guilford

It wouldn't be hard to make a case for any of Connecticut's 24 shoreline towns as a good place for retirement, but Madison and Guilford stand out for several reasons. First of all, they are both far enough east along the shore so that both I-95 and Route 1 aren't hellishly crowded with traffic at all hours of the day and night. Second, both enjoy attractive, walkable downtown shopping/civic/entertainment districts, with Guilford's clustered around the town green and Madison's along the Post Road. The third advantage is ready access to Long Island Sound. Madison is home to 936-acre Hammonasset Beach State Park; it can get hectic and crowded on hot summer days, especially on weekends, but the rest of the year it offers the state's longest beach and miles of seaside hiking trails. Guilford's waterfront offerings are more modest, but the local Chaffinch Island Park is one of Connecticut's best picnic spots. Finally, both towns are already senior-friendly, with suitable housing, strong libraries and a number of active organizations for seniors. Emergency and many other medical needs can be taken care of at the Yale-New Haven Shoreline Medical Center in Guilford.

Urban Allure: New Haven

For some retirees, this is an irresistible package: restaurants of every cuisine and price, live music and theater, art and history museums, lectures and sports events-and all within walking distance or an easy ride via public transportation. Such are the many charms of New Haven, which in recent years has proven to be a desirable destination for bored empty-nesters willing to ignore the city's troubling crime rate as they trade the big house in the suburbs for a city apartment, condo or loft. The key to New Haven's allure is Yale University, of course, with its ambitions, traditions, intellectual fervor and youthful vigor spinning off everything from dinosaur displays and architectural treasures to cabaret acts and all-night falafel joints. But there's more to New Haven than that-there's Southern Connecticut State University and Albertus Magnus College, two major hospitals, a working harbor and easy rail access via Amtrak and Metro-North. And then there's the pizza, which we're happy to rate as the best in the world until someone can prove otherwise. The housing opportunities are varied, but tend to get more interesting (and expensive) the closer you get to the Yale campus.

20 Great Places to Retire

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