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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Price & Promise: Naugatuck

This entry requires a leap of faith and perhaps a change in preconceptions. Naugatuck is a gritty old manufacturing town on the banks of the Naugatuck River just south of Waterbury-and was once the place where everything from Keds to Mounds bars were made. Following a long postindustrial decline, the borough in recent years has found some favor as a bedroom community for the ever-expanding swarms of people who work in Fairfield County but can't afford to live there. They like Naugatuck's cost of living (median condo price: $139,000) and the easy ride up and down Route 8 (except for the damnable Commodore Hull Bridge in Derby/Shelton). But now something new and quite unexpected is in the works. If all goes as planned-and things were moving right along in early spring-a $707 million live/work/play project known as Renaissance Place is going to take advantage of Naugatuck's river frontage and handsome green by constructing a town within a town-1,800 residential units, 500,000 square feet of retail space, 76,000 square feet of office space, a hotel and more on 60 acres. The community (naugatuckrenaissanceplace.com) will be public transit-oriented and independent of national or regional power grids-in short, everything a conscientious boomer is looking for. A happy retirement on the banks of the Naugatuck River? It just might be in the cards.

Beside the Tidal River: Essex

Here's a Connecticut town with an actual pedigree. In a 1996 book by Norm Crampton called The 100 Best Small Towns in America, Essex was deemed the very best of all-and it has wisely used "Best Small Town in America" as a rallying cry ever since. In addition, Essex was recently one of only four Connecticut destinations (along with Mystic Seaport, Mark Twain House and Litchfield Hills/Mayflower Inn) to make it into the best-selling 1,000 Places to See Before You Die. Why all the fuss over this old seafaring town in the lower Connecticut River Valley? Well, Crampton's ranking methods are a little murky, but there's the lovely location on the river, of course, at the very center of what the Nature Conservancy has termed "one of the last great places." And there's the sense of history, evidenced in places such as the Connecticut River Museum and the Griswold Inn, a lively local tavern that claims to be the oldest in the state. Which brings to mind other good spots to eat and drink, and the local playhouse, the galleries and shops, and even, just in case, Middlesex Hospital's Shoreline Medical Center. Active-adult housing is not quite as readily available here as in nearby towns, and what there is tends to be fairly pricey. But isn't that what you'd expect from the "best small town in America"?

Historic Valley Towns: Farmington & Woodbury

Those with a strong sense of history might feel at home in these two well-bred towns, where the very early settlers of Connecticut found sustenance in the riverine soil and enveloping hills. Farmington is easily the larger of the two-an old-line, affluent suburb of Hartford with well-established neighborhoods, good public golf courses, the UConn Health Center, Hill-Stead Museum, many shopping and dining options-and, to be fair, daily traffic adventures on Routes 4 and 10. Farmington has also become a hotbed of condo living for active seniors, with 520 sales over the past two years at a median price of $205,000. Woodbury, located in the Pom-peraug River Valley, offers a far more rural retirement option. Main Street (Route 6) is lined with historic houses, churches and antiques shops. There are also more restaurants here (Good News Cafe, John's Café, Carmen Anthony Fishhouse, Charcoal Chef, Curtis House, etc.) than in any comparably sized town in the state, with the possible exception of Old Saybrook. Add that to the flavor of the Litchfield Hills and Colonial history and you've got an increasingly popular retirement destination.

Lake & Hillside: New Milford

New Milford is home to a nice combination of features for those who might be in the market for a bit of the country life. It's got lots of lakefront acreage on Candlewood Lake (Connecticut's largest), for instance, which gets very busy in summer but is peaceful and lovely the rest of the year. Its large geographic size means there are many back roads and quiet rural retreats offering pleasant views of nearby green pastures, hills and valleys. The Housatonic River runs for miles right down the middle of the town, providing a habitat for fish and game and recreational opportunities for the rest of us. And the town green is one of the most pleasant in the state, surrounded by churches, municipal buildings and businesses. Finally, New Milford is clearly more open than are adjacent towns to the sort of housing that freshly minted retirees are looking for. While neighboring Kent saw sales of only 18 condominiums over the past two years and Washington 10, Bridgewater 3 and Sherman just 1, New Milford had condo sales of 318 at a median price of about $180,000. A wider variety of places where you don't have to mow your own lawn? Now that's a good thing.

Well-Heeled Peace & Quiet: Roxbury & Lyme

When some people think of retirement, they don't see condos or a gated community; they see a sturdy, smallish house, preferably of an older vintage, down a quiet country lane, perhaps with a studio or potting shed attached. They're not looking for organized activities involving shuttle buses and attendance sheets, but rather wish to be left alone to do exactly what they want at precisely their own pace. There are any number of towns in Connecticut where this is possible, but two of the best are Roxbury and Lyme. For one thing, neither town has any condominiums at all, and barely any commercial activity. Roxbury is an uncrowded old farming town that for years has famously served as a retreat for writers (Arthur Miller and William Styron lived and worked here; A.R. Gurney live here now). Most of the farms have by now been turned over to the local land trust, but the smell of hay in the fields remains an intoxicating presence. Lyme, located along the lower eastern banks of the Connecticut River, attracts a saltier crowd, including sailors who put in at lovely, unspoiled Hamburg Cove. A word of warning: Quiet days and nights come at a price-houses in both Roxbury and Lyme are considerably more expensive than the state average.

20 Great Places to Retire

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